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Journal articles on the topic 'Adamantane'

Author: Grafiati

Published: 4 June 2021

Last updated: 28 July 2024

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1

Gadzhiev, G. A., M. V. Giruts, D. S. Vylekzhanina, and G. N. Gordadze. "Formation of С10–С14 Adamantanes from Petroleum Protoadamantanes." Chemistry and Technology of Fuels and Oils 629, no. 1 (2022): 41–49. http://dx.doi.org/10.32935/0023-1169-2022-629-1-41-49.

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In order to study the possibility of enriching jet fuels with diamond-type hydrocarbons to improve their physico-chemical and operational properties, a catalyse with aluminum bromide of narrow 10-degree fractions of marine oil in the range of 190–250°С was carried out. Catalysis products were selected at different times and analysed by chromatomass spectrometry. It is shown that during catalysis there is a complete disappearance of non-adamanthane hydrocarbons and "naphthene background" on mass chromatograms with m/z 135, 149, 163 and 177, with the formation of new, mainly thermodynamically weakly stable isomers of adamantanes, and in subsequent It was found that from the narrow fractions of oil 230–240 and 240–250°C, where there are no hydrocarbons of the series of adamantane series, hydrocarbons of the C12–C14 form from the "naphthene background". It is suggested that transalkylation is the reason for the formation of high-molecular adamantans from low-molecular ones.

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2

Wang, Jian-Wei, Ka-Xi Yu, Xin-Yuan Ji, Hongzhen Bai, Wen-Hua Zhang, Xiurong Hu, and Guping Tang. "Structural Insights into the Host–Guest Complexation between β-Cyclodextrin and Bio-Conjugatable Adamantane Derivatives." Molecules 26, no. 9 (April 21, 2021): 2412. http://dx.doi.org/10.3390/molecules26092412.

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Understanding the host–guest chemistry of α-/β-/γ- cyclodextrins (CDs) and a wide range of organic species are fundamentally attractive, and are finding broad contemporary applications toward developing efficient drug delivery systems. With the widely used β-CD as the host, we herein demonstrate that its inclusion behaviors toward an array of six simple and bio-conjugatable adamantane derivatives, namely, 1-adamantanol (adm-1-OH), 2-adamantanol (adm-2-OH), adamantan-1-amine (adm-1-NH2), 1-adamantanecarboxylic acid (adm-1-COOH), 1,3-adamantanedicarboxylic acid (adm-1,3-diCOOH), and 2-[3-(carboxymethyl)-1-adamantyl]acetic acid (adm-1,3-diCH2COOH), offer inclusion adducts with diverse adamantane-to-CD ratios and spatial guest locations. In all six cases, β-CD crystallizes as a pair supported by face-to-face hydrogen bonding between hydroxyl groups on C2 and C3 and their adjacent equivalents, giving rise to a truncated-cone-shaped cavity to accommodate one, two, or three adamantane derivatives. These inclusion complexes can be terminated as (adm-1-OH)2⊂CD2 (1, 2:2), (adm-2-OH)3⊂CD2 (2, 3:2), (adm-1-NH2)3⊂CD2 (3, 3:2), (adm-1-COOH)2⊂CD2 (4, 2:2), (adm-1,3-diCOOH)⊂CD2 (5, 1:2), and (adm-1,3-diCH2COOH)⊂CD2 (6, 1:2). This work may shed light on the design of nanomedicine with hierarchical structures, mediated by delicate cyclodextrin-based hosts and adamantane-appended drugs as the guests.

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3

Pitushkin, Dmitry, Vladimir Burmistrov, and Gennady Butov. "1-(3-Isoselenocyanatopropyl)adamantane." Molbank 2023, no. 2 (May 15, 2023): M1646. http://dx.doi.org/10.3390/m1646.

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The title compound, 1-(3-isoselenocyanatopropyl)adamantane, was synthesized for the first time from 3-(adamantan-1-yl)propan-1-amine by the two-stage reaction with 1-(3-isocyanopropyl)adamantane as intermediate. The product was characterized by NMR, GC-MS, and elemental analysis.

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4

Leonova, M. V., M. R. Baimuratov, and Yu N. Klimochkin. "Synthesis and reactions of allylic azides of the adamantane series." Журнал органической химии 59, no. 11 (December 15, 2023): 1455–64. http://dx.doi.org/10.31857/s0514749223110071.

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A mixture of nucleophilic substitution product and isomeric azide resulting from [3,3]-sigmatropic rearrangement was obtained by interaction of allyl bromides of adamantane series with sodium azide. Epoxidation reactions of allylic azides of the adamantane series were investigated. The reduction of the obtained trans -2-(adamantan-1-yl)-3-(azidomethyl)oxirane with lithium alumohydride synthesized ( S *)-(adamantan-1-yl)[( S *)-aziridin-2-yl]methanol which, when heated with hydrochloric acid, gives the product of the aziridine ring opening is (1 S *,2 R *)-1-(adamantan-1-yl)-3-chloro-1-hydroxypropan-2-amino chloride.

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5

Guo, Jian Wei, Nian Yun Guan, Sa Liu, Chu Fen Yang, and Le Jie Zhu. "Synthesis and Characterizaion of Adamantane-Containing Quaternary Ammonium Salts." Advanced Materials Research 233-235 (May 2011): 238–41. http://dx.doi.org/10.4028/www.scientific.net/amr.233-235.238.

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To develop the potential use of adamantane derivatives in surfactant field, the adamantyl residue was introduced into the quaternary ammonium salt. The method involved synthesizing N-(1-adamantyl)-N, N-dimethylamine from 1-adamantine and quaternizing with different alkylating agents. Eight adamantane-containing quaternary ammonium salts were prepared and their structures were identified by1H NMR and IR.

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6

Keita, Hamidou. "Adamantane-Functionalized Phthalimide Scaffold: Pathways to Supramolecular Interactions and Drug Discovery." Organics 2, no. 4 (November 11, 2021): 388–94. http://dx.doi.org/10.3390/org2040022.

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Herein, the synthesis of a novel adamantanyl-functionalized phthalimide scaffold is demonstrated. The novel compound could be used as a precursor for various synthetic pathways owing to the generic use of adamantane substituents as the driving force for supramolecular interactions with macrocycles and N-substituted phthalimide derivatives as a core structure in numerous drugs. The adamantanyl-functionalized phthalimide scaffold contains bromide groups on the C4 and C5 positions of the benzene ring, effectively allowing further facile modifications of the scaffold. The structure was fully characterized including single-crystal X-ray crystallography. The crystal structure shows an adamantane moiety at an angle of 115.57(7)° to the phthalimide core, hence sterically freeing the adamantane unit for host–guest interactions.

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7

Abdulhasan, Haithem, Ahmed Al-Yasari, and Rahman Alasadi. "Theoretical Study on Molecular Structure and Electronic Properties of New 1,3-Diaza-adamantan-6-ones Derivatives." Indonesian Journal of Chemistry 20, no. 3 (May 9, 2020): 638. http://dx.doi.org/10.22146/ijc.44403.

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In this study, the structural geometry and vibrational frequencies (IR) of 1,3-Diaza-adamantane-6-ones derivatives including Adamantane (A), 1,3-Diaza-adamantan (D), 1,3-Diaza-adamantan-6-one (DO), 5-Benzyl-1,3-diaza-adamantan-6-one (BD), 5-(4-Hydroxybenzyl)-1,3-diaza-adamantan-6-one (HBD), 5-(4-Methoxybenzyl)-1,3-diaza-adamantan-6-one (MBD), and 5-(4-Hydroxy-3-methoxybenzyl)-1,3-diaza-adamantan-6-one (HMBD) were theoretically studied. In addition, molecular orbital energies, including the highest occupied molecular orbitals (HOMOs), and lowest unoccupied molecular orbitals (LUMOs), and electronic properties of the titled molecules were theoretically studied using the computational method. Optimized molecular structures were obtained by DFT method with the hybrid B3LYP functional at a relatively small basis set of 6-31G. The calculated vibrational wavenumbers were obtained using the same level of the theory mentioned above. The contributions to the molecular orbitals of adamantane and substituted-phenyl groups in the title compounds were determined. Moving from A to HMBD, a decrease in the value of LUMO and total energy are noticed, while an increase in the value of HOMO is noted. These findings are supported by the decreasing in the EHOMO-LUMO gap values. Furthermore, a decrease in the value of ionization potential (IP) is obtained, while an increase in the electronegativity (EA) is observed.

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8

Berndt, Jan-Philipp, Frederik Erb, Lukas Ochmann, Jaqueline Beppler, and Peter Schreiner. "Selective Phthalimido-N-oxyl (PINO)-Catalyzed C–H Cyanation of Adamantane Derivatives." Synlett 30, no. 04 (December 14, 2018): 493–98. http://dx.doi.org/10.1055/s-0037-1610403.

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We present a new method for the selective C(sp3)–H cyanation of adamantane derivatives with PINO as the hydrogen abstracting reagent. A cyano radical is thereby transferred from p -toluenesulfonyl cyanide, allowing the cyanation of adamantane derivatives in up to 71% yield. The protocol presents a novel way to orthogonally functionalized adamantanes that are otherwise difficult to prepare. Mechanistic studies support the hypothesis of a radical pathway.

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9

Kul'kov, M. G., G. T. Salakhidinova, E. A. Vtorushina, R. I. Butyrin, and A. E. Aliev. "Quantification of C10–C14 Adamantanes in High-Viscosity Naphthenic Oils." Нефтехимия 63, no. 5 (December 15, 2023): 654–70. http://dx.doi.org/10.31857/s0028242123050039.

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The paraffin–naphthenic fractions (with boiling points below 310°C) prepared from three high-viscosity naphthenic crude oils, classified as types B1 and B2 (according to Petrov’s classification), were subjected to thiocarbamide complexation. The molecular composition of polycyclic hydrocarbon biomarkers and C11–C13 adamantanes in the oil samples suggested a predominantly marine genotype of the precursor organic matter (OM). The molecular composition also suggested source rocks of a clayey type. Nonetheless, the biomarkers detected in one sample indicated some contribution of terrigenous components to the precursor OM. All the oils were generated under the conditions of the main oil generation zone and, presumably, underwent microbial transformations in the deposits. The compositions of C10–C14 adamantanes in the initial paraffin–naphthenic fraction, in the thiocarbamide adduct, and in the filtrate that remained after the adduction were comparatively characterized for each oil sample. The test conditions allowed us to have adamantane more than 100-fold concentrated (in the adduct), to quantify it in the oils, and to evaluate the concentrations of C11–C14 alkyladamantanes in the oils using adamantane as an internal standard. C10–C14 adamantanes exhibited selective adduction ability, with the extraction ratios of individual components being different. Taking into account these extraction ratios, the component concentrations were evaluated on crude oil basis: 2.7 to 7.6×10–3 wt % for adamantane and 87 to 267×10–3 wt % for total C10–C14 adamantanes. The identification of adamantanes in the initial paraffin–naphthenic fractions, adducts, and filtrates revealed the presence of some other tricyclanes (probable precursors of alkyladamantanes) as well as decaline homologues. Like adamantanes, these compounds exhibited selective ability to complex with thiocarbamide.

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10

Shinsuphan, Nikorn, Sriprajak Krongsuk, and Vittaya Amornkitbamrung. "The Photoluminescence Properties of the Alkali Metals Functionalized Adamantane Studied by Using Linear-Response Time-Dependent Density Functional Theory (TD-DFT) Calculations." Advanced Materials Research 1131 (December 2015): 117–22. http://dx.doi.org/10.4028/www.scientific.net/amr.1131.117.

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The photoluminescence properties of pristine adamantane molecule have been calculated by time-dependent density functional theory (TD-DFT) within the hybrid functional level. This study aims to investigate the luminescence properties of the pristine adamantane molecule and its functionalized with neutral and ion of alkali metal to form C10H16-nXn structure (where X is Li, Li+, Na and Na+ atoms, n=1). The electronic gap of the pristine adamantane (7.15 eV) is too wide, leading to an insulator property. While all the functionalized adamantanes exhibit semiconducting behavior. The absorption and emission energies of the original structure are 6.51 eV and 5.63 eV, respectively which are in good agreement with experimental results. The pure adamantane exhibits a broad photoluminescence peak in the ultraviolet region (UV). The Stokes shift of the transition between vertical and emission is 0.88 eV which agrees well with the previous work that measures the Stokes shift of 0.7 eV. The modification of adamantane indicates that the absorption and emission gaps substantially decreases. Substituting with alkali metal causes the photoluminescence onset can be shifted from the UV to the near-IR region. These results suggest that pure and the alkali metal functionalized adamantane molecules are promoting as candidate materials for the opto-electronic applications in the ultraviolet to infrared spectral regions.

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11

Maehara, Takayuki, Hiroshi Hashimoto, and Joji Ohshita. "Synthesis and Heat Resistance of Arylenedioxy-organosilanylene Polymers with Adamantane Units." Zeitschrift für Naturforschung B 64, no. 11-12 (December 1, 2009): 1567–70. http://dx.doi.org/10.1515/znb-2009-11-1241.

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Arylenedioxy-organosilanylene polymers with adamantane units in the backbone were prepared by Rh-catalyzed dehydrocoupling of bis(4-hydroxyphenyl)adamantanes with organohydrosilanes, and their heat resistance was evaluated by thermogravimetric analysis in nitrogen. Among these polymers, the highest Td10 (10% weight loss temperature) of 547 °C was achieved for polymer 2a prepared from 1,3-bis(4-hydroxyphenyl)adamantane and phenylsilane. Polymer 2a exhibited good heat resistance even in air with Td10 = 387 °C, and standing of the polymer at 150 °C for 8 h resulted in no evident weight loss

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12

Pardali, Vasiliki, Erofili Giannakopoulou, Athina Konstantinidi, Antonios Kolocouris, and Grigoris Zoidis. "1,2-Αnnulated Adamantane Heterocyclic Derivatives as Anti-Influenza Α Virus Agents." Croatica chemica acta 92, no. 2 (2019): 211–28. http://dx.doi.org/10.5562/cca3540.

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In this report we review our results on the development of 1,2-annulated adamantane heterocyclic derivatives and we discuss the structure-activity relationships obtained from their biological evaluation against influenza A virus. We have designed and synthesized numerous potent 1,2-annulated adamantane analogues of amantadine and rimantadine against influenza A targeting M2 protein the last 20 years. For their synthesis we utilized the key intermediates 2-(2-oxoadamantan-1-yl)acetic acid and 3-(2-oxoadamantan-1-yl)propanoic acid, which were obtained by a simple, fast and efficient synthetic protocol. The latter involved the treatment of protoadamantanone with different electrophiles and a carbon-skeleton rearrangement. These ketoesters offered a new pathway to the synthesis of 1,2-disubstituted adamantanes, which constitute starting materials for many molecules with pharmacological potential, such as the 1,2-annulated adamantane heterocyclic derivatives. To obtain additional insight for their binding to M2 protein three structurally similar 1,2-annulated adamantane piperidines, differing in nitrogen position, were studied using molecular dynamics (MD) simulations in palmitoyl-oleoyl-phosphatidyl-choline (POPC) hydrated bilayers.

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13

Pabbaraju, Kanti, Sallene Wong, Dmitri K. Kits, and Julie D. Fox. "Adamantane Resistance in Seasonal Human Influenza A Viruses from Calgary, Alberta (January 2007 to August 2008)." Canadian Journal of Infectious Diseases and Medical Microbiology 21, no. 2 (2010): e87-e91. http://dx.doi.org/10.1155/2010/710149.

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The available antivirals for the treatment and prophylaxis of influenza A infections include the adamantanes (amantadine and rimantadine), which are matrix (M2) protein inhibitors, and the neuraminidase inhibitors (oseltamivir and zanamivir). Resistance to the adamantanes is conferred by mutations at amino acid positions 26, 27, 30, 31 or 34 within the M2 protein of influenza A viruses. A significant increase in adamantane resistance has been reported worldwide since 2003, reflected by a similar increase in Canada. The present study reports on the frequency of adamantane resistance in seasonal influenza A viruses in Calgary, Alberta, for the period between January 2007 and August 2008, as an update to the previous report. Positive influenza A samples (221 original patient specimens and 34 isolates obtained by viral culture) were analyzed for changes in the critical amino acid residues of theM2gene. The amplification and sequencing of regions that confer adamantane resistance directly from RNA extracts of clinical samples (without previous culture) makes this approach a fast and efficient process for monitoring resistance. The results showed that the frequency of resistance varied from 37.5% to 49.2% in circulating influenza A H3N2 virus strains (n=213) between January 2007 and April 2007. The frequency of resistance increased to 100% in May 2007, after which all H3N2 viruses were resistant until the end of the monitoring period. All resistant H3N2 viruses contained the serine to asparagine substitution at amino acid position 31. Resistance was not observed in the H1N1 viruses tested (n=39) within this monitoring period. The level of adamantane resistance in H3N2 viruses continues to remain high since resistant viruses became the prevalent circulating strains in 2005. Recent reports have indicated that the currently circulating swine-origin influenza A H1N1 subtype viruses are adamantane resistant. It is, thus, important to continue to monitor seasonal influenza A viruses for antiviral resistance markers to ensure optimal prophylaxis and treatment.

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14

Nowakowska, Monika, Caryn Gamble, and Demetrius C. Levendis. "Bis(adamantan-1-aminium) carbonate." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (March 24, 2012): o1159. http://dx.doi.org/10.1107/s1600536812011828.

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In the title compound, 2C10H18N+·CO32−, the adamantan-1-aminium cation forms three N—H...O hydrogen bonds to three carbonate ions, resulting in a layer parallel to (001) with the adamantane groups located on its surface so that adjacent layers form only C—H...H—C contacts. The carbonate anions occupy special positions of 32 symmetry, whereas the adamantan-1-aminium cations occupy special positions of 3 symmetry.

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15

Stankova, Ivanka, Radoslav Chayrov, Michaela Schmidtke, Dancho Danalev, Liudmila Ognichenko, Anatoly Artemenko, Valery Shapkin, and Victor Kuz'min. "Quantitative structure-activity relationship modelling of influenza M2 ion channels inhibitors." Journal of the Serbian Chemical Society 86, no. 7-8 (2021): 625–37. http://dx.doi.org/10.2298/jsc200509036s.

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A series of adamantane derivatives (rimantadine and amantadine) incorporating amino-acid residues are investigated by simplex representation of molecular structure (SiRMS) approach in order to found correlation between chemical structures of investigated compounds and obtained data for antiviral activity and cytotoxicity. The obtained data from QSAR analysis show that adamantane derivatives containing amino acids with short aliphatic non-polar residues in the lateral chain will have good antiviral activity against the tested virus A/H3N2, strain Hong Kong/68 with low cytotoxicity. QSAR experiments and in vitro data also show good correlation and reveal that modified adamantine derivatives including guanidated in the lateral chain amino acid and ?-amino acids as substituents show low to none activity.

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16

Hewajuli, Dyah Ayu, and NLPI Dharmayanti. "Efficacy, Mechanism and Antiviral Resistance of Neuraminidase Inhibitors and Adamantane against Avian Influenza." Indonesian Bulletin of Animal and Veterinary Sciences 29, no. 2 (December 4, 2019): 61. http://dx.doi.org/10.14334/wartazoa.v29i2.1951.

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Vaccination and antiviral drug are often used to control influenza. However, the effectiveness of vaccine was impaired due to the emergence of new variant of virus strain. Antiviral drug consists of prophylactic and curative substances, namely M2 ion channel inhibitors (adamantane; amantadine and rimantadine) and neuraminidase (NA) inhibitors (NAIs; oseltamivir, zanamivir, peramivir, laninamivir). The synthesis and modification of antiviral neuraminidase (NA) inhibitors (NAIs) and adamantanes increased the antiviral effectiveness. The mechanism of the neuraminidase inhibitor is to prevent influenza infection by inhibiting the release of the virus from internal cells. Adamantane is antiviral drug that selectively inhibits the flow of H+ ions through M2 protein to prevent the uncoating virus particles getting into the endosome. The substitution of (H275Y, S247N, I223L, K150N, R292K, I222T, R152K, R118K, E119V) on NA protein caused resistance of avian influenza virus against the neuraminidase inhibitor. The combination of mutations (S247N, I223L, K150N) increased the resistance of influenza A (H5N1) virus. The diffusion of adamantane resistance varies among HA subtypes, the species of host, the period of isolation, and region. Mutations at residues of 26, 27, 30, 31 or 34 transmembrane M2 protein caused adamantane resistance. The unique substitution (V27I) of M2 protein of clade 2.3.2 H5N1 subtype isolated in Indonesia in 2016 has been contributed to the amantadine resistance. Antiviral combination of M2 ion channel inhibitors and neuraminidase (NA) inhibitors is effective treatments for the resistance.

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17

Gordadze, G. N., A. V. Vasil'eva, D. S. Vylekzhanina, G. A. Gadzhiev, and O. A. Stokolos. "Comparison of the Hydrocarbon Distribution in Thermolysis Products of Asphaltenes, Resins, and Acids Isolated from Weakly Transformed Crude Oil from the Anastasievsko-Troitskoe Oil Field (Horizon IV)." Нефтехимия 63, no. 4 (December 15, 2023): 485–93. http://dx.doi.org/10.31857/s0028242123040032.

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Regular trends in the distribution of hydrocarbon biomarkers (n-alkanes, isoprenanes, steranes, and terpanes) and hydrocarbons of the adamantane series in low-maturity crude oil from the Anastasievsko-Troitskoe oil field (horizon IV) and in products formed by thermolysis of asphaltenes, resins, and acids from this oil were studied by gas chromatography–mass spectrometry. Thermolysis of high-molecular-mass oil precursors yields the same hydrocarbons (HCs) as those present in the initial oil, and also protoadamantanes (precursors of adamantanes). HCs of the adamantane series are not formed, and their presence in this crude oil is due to their supply from other oil source strata. The experiments show that the n-alkanes present in the initial oil in small amounts are released under more severe conditions.

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18

Grob, Cyril A., and Pawel Sawlewicz. "The mild bromination of adamantane and (trimethylsilyl) adamantanes." Helvetica Chimica Acta 71, no. 6 (September 28, 1988): 1508–10. http://dx.doi.org/10.1002/hlca.19880710616.

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19

Моkhоv, V. М., G. М. Butоv, and I. А. Novakov. "1,3-DEHYDROADAMANTANE AND ITS DERIVATIVES: A VERSATILE SYNTHETIC PLATFORM FOR PREPARATION OF FUNCTIONAL COMPOUNDS WITH A CAGE STRUCTURE. A REVIEW." Доклады Российской академии наук. Химия, науки о материалах 511, no. 1 (July 1, 2023): 3–36. http://dx.doi.org/10.31857/s2686953522600891.

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A promising strategy for the synthesis of a functional compounds with framework structure is using of 1,3‑dehydroadamantane (tetracyclo[3.3.1.1.3,7.0.1,3]decane, 1,3-DHA, bridging [3.3.1]propellane) and its derivatives, which are able to restoration of adamantane structure in their reactions. The review provides information on the methods for the synthesis of 1,3-DHA, spectral characteristics, probable intermediates generated from propellanes, and the advantages of using – low-stage syntheses of hardly available adamantine derivatives, atomic precision, and “green chemistry”. The reactions of 1,3-DHA with a wide range of organic compounds are considered, a comparative assessment of its reactivity with respect to CH-, NH-, OH- and SH-acids, as well as arenes, hydantoins, and heterocyclic compounds is carried out. New chemo- and regioselective methods for the one-step introduction of a 1-adamantyl group into the molecules of various substrates are classified. Particular attention is paid to the reactions of 1,3-DHA with various C–H acids, which make it possible to easily form C–CAd bonds to obtain hard-to-reach adamantane derivatives. The influence of pKa of the substrate on the selectivity of the reactions was shown. Low-step methods for the synthesis of new adamantane derivatives, which have shown high activity as hsEH epoxide hydrolase inhibitors and antitumor agents, are described.

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20

Isaev, Sergei D., Nataliya F. Karpenko, Aleksandr G. Yurchenko, Luděk Vodička, Valentin I. Kadentsev, and Pavel Zachař. "Compounds of aziadamantane type: Mass spectrometric study." Collection of Czechoslovak Chemical Communications 54, no. 3 (1989): 691–98. http://dx.doi.org/10.1135/cccc19890691.

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Azi and hydrazi derivatives of adamantane,adamantanone and diamantane were studied by mass spectrometry. The EI spectra of azi derivatives lack completely molecular ions; the presence of abundant dehydroadamantane or dehydrodiamantane ions corresponds to elimination of nitrogen molecule from the molecular ion. Comparison of the EI ionization with photolysis or pyrolysis allowed to deduce some analogies and to suggest the mechanism of decomposition of the molecular ion.

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21

Bakkali, Bouchra El, Guido Trautwein, Juan Alcañiz-Monge, and Santiago Reinoso. "Zirconia-supported 11-molybdovanadophosphoric acid catalysts: effect of the preparation method on their catalytic activity and selectivity." Acta Crystallographica Section C Structural Chemistry 74, no. 11 (October 18, 2018): 1334–47. http://dx.doi.org/10.1107/s2053229618013013.

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The oxidation of adamantane with hydrogen peroxide catalyzed by zirconia-supported 11-molybdovanadophosphoric acid is shown to be a suitable green route for the synthesis of adamantanol and adamantanone. This work evaluates how the catalyst activity and selectivity are affected by some of its preparative parameters, such as the method for supporting the catalytically active heteropoly acid over the zirconia matrix or the pretreatments applied to the resulting materials before being used as heterogeneous catalysts. Our results indicate that the most effective catalysts able to maintain their activity after several reaction runs are those prepared by following the sol-gel route, whereas the most selective catalysts are those obtained by impregnation methods. Moreover, the calcination temperature has also been identified as a relevant parameter influencing the performance of catalysts based on supported heteropoly acids. The increasing catalytic activity observed over several consecutive reaction runs has been attributed to the formation of peroxo derivatives of polyoxometalate clusters at the surface of the catalyst and their accumulation after each reaction cycle.

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22

Pradeep S, Midhun Manohar, and Nihal Kulkarni. "Mapping the Resistance Potential of Influenza’s H + Channel Using an Anti." International Journal of Fundamental and Applied Sciences (IJFAS) 6, no. 4 (December 30, 2017): 31–33. http://dx.doi.org/10.59415/ijfas.v6i4.112.

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One of the biggest problems faced by biotechnologists and pharmacologists all over the world is the difficulty in predicting the strains of viral diseases that are coming into circulation. The problem becomes much worse when it becomes difficult to predict the virus’s resistance pattern.Influenza A virus has many factors that play a role in its infection cycle. Here, we are trying to study how the virus exhibits resistance against an anti-viral blocker.The blocker that is used in this case is amino-adamantane antiviral inhibitor (adamantine).

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23

Causey, Patrick W., Igor Dubovyk, and Clifford C. Leznoff. "Syntheses and characterization of phthalonitriles and phthalocyanines substituted with adamantane moieties." Canadian Journal of Chemistry 84, no. 10 (October 1, 2006): 1380–87. http://dx.doi.org/10.1139/v06-096.

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The reaction of 3,4,5,6-tetrafluorophthalonitrile with 1-adamantanol, 1-adamantylamine, 1-adamantanemethanol, and 1-adamantaneethanol gave 4,5-di-(1-adamantyloxy)-3,6-difluorophthalonitrile, 4,5-di-(1-adamantylamino)-3,6-difluorophthalonitrile, 4-(1-adamantylamino)-3,5,6-trifluorophthalonitrile, 3,4,5,6-tetra-(1-adamantylmethoxy)phthalonitrile, and 3,4,5,6-tetra-(1-adamantylethoxy)phthalonitrile, respectively. The conversion of these tetrasubstituted phthalonitriles to magnesium, nickel, and metal-free phthalocyanines was demonstrated. These highly hindered phthalocyanines exhibited interesting red shifts in their UV–vis spectra.Key words: highly hindered adamantane phthalocyanines, adamantylphthalonitriles.

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Schraml, Jan, and Jan Čermák. "29Si and 13C nmr spectra of trimethylsiloxy and hydroxy adamantanes reinvestigated at low concentration in deuteriochloroform solutions." Collection of Czechoslovak Chemical Communications 55, no. 2 (1990): 452–59. http://dx.doi.org/10.1135/cccc19900452.

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29Si and 13C NMR chemical shifts are reported for mono- and bis(trimethylsiloxy)adamantanes as well as for mono- and dihydroxyadamantanes dissolved in deuteriochloroform. The chloroform induced changes in 29Si and 13C chemical shifts can be qualitatively accounted for by hydrogen-bonding considering basicity and solvent accessibility of oxygen atoms in the solute molecules. The steric effects observed on the 29Si shifts are not due to an interaction of the terminal hydrogen atoms of the trimethylsilyl groups but are due to proximity of two oxygen atoms on one cyclohexane ring of the adamantane skeleton.

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25

Dragomanova, Stela, and Velichka Andonova. "Adamantane-containing drug delivery systems." Pharmacia 70, no. 4 (October 11, 2023): 1057–66. http://dx.doi.org/10.3897/pharmacia.70.e111593.

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Adamantane is a weakly functional hydrocarbon widely used to develop new drug molecules to improve their pharmacokinetic and pharmacodynamic parameters. The compound has an affinity for the lipid bilayer of liposomes, enabling its application in targeted drug delivery and surface recognition of target structures. This review presents the available data on developed liposomes, cyclodextrin complexes, and adamantane-based dendrimers. Adamantane has been used in two ways – as a building block to which various functional groups are covalently attached (adamantane-based dendrimers) or as a part of self-aggregating supramolecular systems, where it is incorporated based on its lipophilicity (liposomes) and strong interaction with the host molecule (cyclodextrins). Adamantane represents a suitable structural basis for the development of drug delivery systems. The study of adamantane derivatives is a current topic in designing safe and selective drug delivery systems and molecular carriers.

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Salvatori, Alejandro, Philippe Negrier, Araceli Aznar, María Barrio, Josep Lluís Tamarit, and Pol Lloveras. "Colossal barocaloric effects in adamantane derivatives for thermal management." APL Materials 10, no. 11 (November 1, 2022): 111117. http://dx.doi.org/10.1063/5.0127667.

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Plastic crystals are currently attracting interest because their solid-state caloric functionality could be used to tackle climate change in two critical areas: (i) more environmentally friendly cooling and heating driven by pressure and (ii) passive waste heat management. Here, we suggest that plastic crystals could also be used for active pressure-assisted (i.e., barocaloric) waste heat management. In contrast to the barocaloric cooling/heating cycle, for active barocaloric waste heat management, the hysteresis may not be a constraint and transition temperatures above ambient are usually desired. In contrast to passive waste heat management, the application of pressure can be an advantage to actively control the absorption and delivery of heat by the plastic crystal. Here, we have investigated the pressure-induced caloric response at the first-order phase transitions occurring above room temperature of three plastic crystals derived from adamantane: 1-adamantanol, 2-adamantanol, and 2-methyl-2-adamantanol. Colossal barocaloric effects have been found for two of them under small pressure changes of 50 MPa. This behavior occurs thanks to a colossal transition entropy change and a large transition sensitivity to pressure, which can simultaneously take place due to enormous transition volume changes. The balance between configurational and volumic entropy changes at the transition has also been discussed. For 2-adamantanol, in addition to the transition to the plastic phase, the less energetic triclinic-to-monoclinic transition at lower temperatures has also been analyzed. The transition temperatures above ambient make these compounds suitable for waste heat management and, thanks to a small hysteresis, also for industrial cooling and heat pumping.

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Shchapin, Igor Yu, Dzhamalutdin N. Ramazanov, Andrey I. Nekhaev, Roman S. Borisov, Evgeny A. Buravlev, and Anton L. Maximov. "One-Stage Catalytic Oxidation of Adamantane to Tri-, Tetra-, and Penta-Ols." Catalysts 11, no. 8 (August 23, 2021): 1017. http://dx.doi.org/10.3390/catal11081017.

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Tertiary tetraols of adamantane (C10H16, Tricyclo[3.3.1.1(3,7)]decan) have been widely used for the synthesis of highly symmetric compounds with unique physical and chemical properties. The methods for one-stage simultaneously selective, deep, and cheap oxidation of adamantane to tetraols of different structures have not yet been developed. In this research, chemically simple, cheap, and environmentally friendly reagents are used and that is the first step in this direction. The conditions, under which the impact of a hydrogen peroxide water solution on adamantane dissolved in acetonitrile results in full conversion of adamantane and formation of a total 72% mixture of its tri-, tetra-, and penta-oxygenated products, predominantly poliols, have been found. Conversion and adamantane oxidation depth are shown to depend on the ratio of components of the water-acetonitrile solution and the method of oxidizer solution introduction when using the dimer form of 1:1 dimethylglyoxime and copper dichloride complex as a catalyst. Under the conditions of mass-spectrometry ionization by electrons (70 eV), fragmentation across three C–C bonds of the molecular ions framework of adamantane tertiary alcohols Ad(OH)n in the range n = 0–4 increases linearly with the rise of n.

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Oh, Ding Yuan, and Aeron C. Hurt. "A Review of the Antiviral Susceptibility of Human and Avian Influenza Viruses over the Last Decade." Scientifica 2014 (2014): 1–10. http://dx.doi.org/10.1155/2014/430629.

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Antivirals play an important role in the prevention and treatment of influenza infections, particularly in high-risk or severely ill patients. Two classes of influenza antivirals have been available in many countries over the last decade (2004–2013), the adamantanes and the neuraminidase inhibitors (NAIs). During this period, widespread adamantane resistance has developed in circulating influenza viruses rendering these drugs useless, resulting in the reliance on the most widely available NAI, oseltamivir. However, the emergence of oseltamivir-resistant seasonal A(H1N1) viruses in 2008 demonstrated that NAI-resistant viruses could also emerge and spread globally in a similar manner to that seen for adamantane-resistant viruses. Previously, it was believed that NAI-resistant viruses had compromised replication and/or transmission. Fortunately, in 2013, the majority of circulating human influenza viruses remain sensitive to all of the NAIs, but significant work by our laboratory and others is now underway to understand what enables NAI-resistant viruses to retain the capacity to replicate and transmit. In this review, we describe how the susceptibility of circulating human and avian influenza viruses has changed over the last ten years and describe some research studies that aim to understand how NAI-resistant human and avian influenza viruses may emerge in the future.

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Harvey, Pierre D., Denis F. R. Gilson, and Ian S. Butler. "Phase transitions and molecular motions in adamantane derivatives: 1-adamantanol." Canadian Journal of Chemistry 65, no. 8 (August 1, 1987): 1757–60. http://dx.doi.org/10.1139/v87-296.

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An order–disorder transition occurs in 1-adamantanol at 359 K on heating and at 342 K on cooling, with transition entropies of 36 and 34 J K−1 mol−1, respectively. FT-ir spectra show that free hydroxyl groups exist in the high temperature phase, but the majority of the O—H groups remain hydrogen bonded. The barrier to adamantyl group rotation in the low-temperature phase, determined from proton spin–lattice relaxation time measurements, is 20.9 Kj mol−1, and the barrier to rotation in the high-temperature phase is 35.0 kJ mol−1.

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30

D’yachenko, Vladimir, Dmitry Danilov, Yaroslav Kuznetsov, Semyon Moiseev, Vladimir Mokhov, Vladimir Burmistrov, and Gennady Butov. "Synthesis and Properties of 1,3-Disubstituted Ureas Containing (Adamantan-1-yl)(phenyl)methyl Fragment Based on One-Pot Direct Adamantane Moiety Inclusion." Molecules 28, no. 8 (April 19, 2023): 3577. http://dx.doi.org/10.3390/molecules28083577.

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A one-stage method for the preparation of 1-[isocyanato(phenyl)methyl]adamantane containing a phenylmethylene fragment located between the adamantane fragment and the isocyanate group, and 1-[isocyanato(phenyl)methyl]-3,5-dimethyladamantane with additional methyl groups at the nodal positions of adamantane, with a yield of 95% and 89%, respectively, is described. The method includes the direct inclusion of an adamantane moiety through the reaction of phenylacetic acid ethyl ester with 1,3-dehydroadamantane or 3,5-dimethyl-1,3-dehydroadamantane followed by the hydrolysis of the obtained esters. The reaction of 1-[isocyanato(phenyl)methyl]adamantane with fluorine(chlorine)-containing anilines gave a series of 1,3-disubstituted ureas with 25–85% yield. 1-[Isocyanato(phenyl)methyl]-3,5-dimethyladamantane was involved in the reactions with fluorine(chlorine)-containing anilines and trans-4-amino-(cyclohexyloxy)benzoic acid to obtain another series of ureas with a yield of 29–74%. The resulting 1,3-disubstituted ureas are promising inhibitors of the human soluble epoxide hydrolase (hsEH).

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Baykova, S. O., S. V. Baykov, A. A. Petrov, V. V. Bumistrov, and V. P. Boyarskiy. "Synthesis and properties of 1,3-disubstituted ureas bearing adamantyl and pyridin(quinolin)yl moieties." Журнал органической химии 59, no. 7 (July 15, 2023): 910–19. http://dx.doi.org/10.31857/s0514749223070054.

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A series of 1,3-disubstituted ureas containing pyridine (quinoline) and lipophilic adamantane moieties was synthesized by the reaction of 1,1-dimethyl-3-(hetaryl)ureas with amine hydrochlorides (13 compounds, 53-94% yields). The synthesized compounds differ from each other in the substitution position of the adamantane fragment, the structure of the alkyl linker between the adamantane fragment and the amide group, and the type of heterocyclic substituent. They are potentially targeted inhibitors of human soluble epoxide hydrolase (sEH).

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32

Burmistrov, Vladimir, Dmitry Pitushkin, and Gennady Butov. "New Facile Synthesis of Adamantyl Isothiocyanates." SynOpen 01, no. 01 (March 2017): 0121–24. http://dx.doi.org/10.1055/s-0036-1588574.

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A series of adamantyl isothiocyanates containing different substituents in the nodal positions of adamantane or spacers between the adamantane and isothiocyanate group have been synthesised by using the reaction of the corresponding adamantyl amines with phenyl isothiocyanate.

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33

Senge, Mathias O., and Nitika Grover. "Synthetic Advances in the C–H Activation of Rigid Scaffold Molecules." Synthesis 52, no. 22 (July 3, 2020): 3295–325. http://dx.doi.org/10.1055/s-0040-1707884.

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The remarkable structural and electronic properties of rigid non-conjugated hydrocarbons afford attractive opportunities to design molecular building blocks for both medicinal and material applications. The bridgehead positions provide the possibility to append diverse functional groups at specific angles and in specific orientations. The current review summarizes the synthetic development in CH functionalization of three rigid scaffolds namely: (a) cubane, (b) bicyclo[1.1.1]pentane (BCP), (c) adamantane.1 Introduction2 Cubane2.1 Cubane Synthesis2.2 Cubane Functionalization3 Bicyclo[1.1.1]pentane (BCP)3.1 BCP Synthesis3.2 BCP Functionalization4 Adamantane4.1 Adamantane Synthesis4.2 Adamantane Functionalization5 Conclusions and Outlook

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34

Todd, Matthew, and Radim Hrdina. "Synthesis of 1,2-Disubstituted Adamantane Derivatives by Construction of the Adamantane Framework." Molecules 28, no. 22 (November 16, 2023): 7636. http://dx.doi.org/10.3390/molecules28227636.

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This review summarizes achievements in the synthesis of 1,2-disubstituted adamantane derivatives by the construction of the tricyclic framework either by total synthesis or by ring expansion/contraction reactions of corresponding adamantane homologues. It is intended to complement reviews focusing on the preparation of 1,2-disubstituted derivatives by C–H functionalization methods.

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35

Jelínková, Kristýna, Jelica Kovačević, Eva Wrzecionková, Zdeňka Prucková, Michal Rouchal, Lenka Dastychová, and Robert Vícha. "Binding study on 1-adamantylalkyl(benz)imidazolium salts to cyclodextrins and cucurbit[n]urils." New Journal of Chemistry 44, no. 17 (2020): 7071–79. http://dx.doi.org/10.1039/d0nj00738b.

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Adamantane-based imidazolium salts with flexible linkers between the adamantane cage and imidazolium core were prepared. Their supramolecular behaviour towards the natural cyclodextrins α-CD, β-CD and γ-CD and cucurbit[n]urils (n = 7, 8) was studied.

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36

Kauscher, Ulrike, and Bart Jan Ravoo. "Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin–carbohydrate recognition." Beilstein Journal of Organic Chemistry 8 (September 17, 2012): 1543–51. http://dx.doi.org/10.3762/bjoc.8.175.

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Cyclodextrin vesicles are versatile models for biological cell membranes since they provide a bilayer membrane that can easily be modified by host–guest interactions with functional guest molecules. In this article, we investigate the multivalent interaction of the lectin concanavalin A (ConA) with cyclodextrin vesicles decorated with mannose–adamantane conjugates with one, two or three adamantane units as well as one or two mannose units. The carbohydrate–lectin interaction in this artificial, self-assembled glycocalyx was monitored in an agglutination assay by the increase of optical density at 400 nm. It was found that there is a close relation between the carbohydrate density at the cyclodextrin vesicle surface and the multivalent interaction with ConA, and the most efficient interaction (i.e., fastest agglutination at lowest concentration) was observed for mannose–adamantane conjugates, in which both the cyclodextrin–adamantane and the lectin–mannose interaction is inherently multivalent.

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37

Doi, Hideo, and Misako Aida. "Hydration of Adamantane Skeleton: Water Assembling around Amantadine and Halo-substituted Adamantanes." Chemistry Letters 42, no. 3 (March 5, 2013): 292–94. http://dx.doi.org/10.1246/cl.2013.292.

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38

Kumarathasan, Rajkumar, and Norman R. Hunter. "OXIDATION OF ADAMANTANE TO 1-ADAMANTANOL USING TETRA-N-BUTYLAMMONIUM OXONE." Organic Preparations and Procedures International 23, no. 5 (October 1991): 651–54. http://dx.doi.org/10.1080/00304949109457919.

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39

Song, Sun-Jung, Kyoung Seok Kim, Kyung Hwan Kim, Jong Beom Kim, Jong-Ho Kim, Keun-Sik Kim, Honghyun Shin, and Dong Lyun Cho. "Highly Selective Production of 2-Adamantanone by Photocatalytic Oxidation of Adamantane." Chemistry Letters 37, no. 10 (October 5, 2008): 1052–53. http://dx.doi.org/10.1246/cl.2008.1052.

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40

Zahid, Maryam, M. Khawar Rauf, Michael Bolte, and Shahid Hameed. "Adamantane-1-thioamide." Acta Crystallographica Section E Structure Reports Online 65, no. 8 (July 18, 2009): o1891. http://dx.doi.org/10.1107/s1600536809027470.

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41

Raine, Alan L., Craig M. Williams, and Paul V. Bernhardt. "1-(Phenylethynyl)adamantane." Acta Crystallographica Section E Structure Reports Online 58, no. 12 (November 30, 2002): o1439—o1440. http://dx.doi.org/10.1107/s1600536802021542.

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42

Černochová, Jarmila, Andrea Čablová, Michal Rouchal, Marek Nečas, and Robert Vícha. "1-(Bromomethyl)adamantane." Acta Crystallographica Section E Structure Reports Online 67, no. 7 (June 25, 2011): o1820. http://dx.doi.org/10.1107/s1600536811023695.

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43

Tanaka, Kazuo, Tatsuhiro Hiraoka, Fumiyasu Ishiguro, Jong-Hwan Jeon, and Yoshiki Chujo. "Adamantane ionic liquids." RSC Advances 4, no. 53 (2014): 28107. http://dx.doi.org/10.1039/c4ra02575j.

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44

Myint, Mo Aung, Jason R. Price, and Eng Wui Tan. "Adamantane-1,2-diol." Acta Crystallographica Section E Structure Reports Online 62, no. 3 (February 24, 2006): o1139—o1140. http://dx.doi.org/10.1107/s1600536806003734.

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45

Mohamed, Sharmarke, Durga Prasad Karothu, and Panče Naumov. "Using crystal structure prediction to rationalize the hydration propensities of substituted adamantane hydrochloride salts." Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 72, no. 4 (July 16, 2016): 551–61. http://dx.doi.org/10.1107/s2052520616006326.

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The crystal energy landscapes of the salts of two rigid pharmaceutically active molecules reveal that the experimental structure of amantadine hydrochloride is the most stable structure with the majority of low-energy structures adopting a chain hydrogen-bond motif and packings that do not have solvent accessible voids. By contrast, memantine hydrochloride which differs in the substitution of two methyl groups on the adamantane ring has a crystal energy landscape where all structures within 10 kJ mol−1of the global minimum have solvent-accessible voids ranging from 3 to 14% of the unit-cell volume including the lattice energy minimum that was calculated after removing water from the hydrated memantine hydrochloride salt structure. The success in using crystal structure prediction (CSP) to rationalize the different hydration propensities of these substituted adamantane hydrochloride salts allowed us to extend the model to predict under blind test conditions the experimental crystal structures of the previously uncharacterized 1-(methylamino)adamantane base and its corresponding hydrochloride salt. Although the crystal structure of 1-(methylamino)adamantane was correctly predicted as the second ranked structure on the static lattice energy landscape, the crystallization of aZ′ = 3 structure of 1-(methylamino)adamantane hydrochloride reveals the limits of applying CSP when the contents of the crystallographic asymmetric unit are unknown.

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46

Lomas, John S., Christine Cordier, and Sylvette Briand. "Thermal fragmentation of 1-substituted spiro[adamantane-2,2′-adamantane] derivatives." J. Chem. Soc., Perkin Trans. 2, no. 5 (1996): 865–70. http://dx.doi.org/10.1039/p29960000865.

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47

Lomas, John S., Christine Cordier, Sylvette Briand, and Jacqueline Vaissermann. "Thermal rearrangement of 1-substituted spiro[adamantane-2,2′-adamantane] derivatives." J. Chem. Soc., Perkin Trans. 2, no. 5 (1996): 871–76. http://dx.doi.org/10.1039/p29960000871.

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48

Odyntsova, V. M. "The main optical characteristics of UV-spectra of 5-(adamantane-1-yl)-4R-1,2,4-triazole-3-thiones derivatives." Farmatsevtychnyi zhurnal, no. 5 (September 4, 2018): 57–62. http://dx.doi.org/10.32352/0367-3057.5.15.01.

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The development of pharmaceutical chemistry confronts molecular spectroscopy the problem of calculating the electronic states, assumptions and explanations of the various properties of complex organic compounds. In recent years, following the basic optical characteristics of the electronic absorption spectra: the wave number of maximum absorption – νmax (in cm-1), the half-width of the absorption bands of – ∆ν1/2 (cm-1), the integral intensity of the absorption band (in l/mol·cm2), the oscillator strength of the electronic transition – f, the matrix element of the transition of electrons – Mik. began widely used. These constants allow you to determine the chromophores in the investigated substances, to establish the probability and the resolution of the electrons’ transition. Our goal was the calculation and study of the basic optical characteristics of the electronic absorption spectra of 5-(adamantane-1-yl)-4R-1,2,4-triazole-3-thione, namely 5-(adamantane-1-yl)-4-methyl-1,2,4-triazole-3-thione and 5-(adamantane-1-yl)-4-phenyl-1,2,4-triazole-3-thione derivatives. When deciding about the purity of the compounds we used melting point, thin layer chromatography and the results of elemental analysis. UV spectra of the investigated compounds was measured with a spectrophotometer Specord 200-222U214 (Germany). Elemental analyzer GmbH (Germany) was used for carrying out the elemental analysis. It is determined that the values of the half-width Δν½ and integrated intensity of the absorption bands (A), the oscillator strength (f) and matrix element of the transition (Mik) can be used as an important constants of 5-(adamantane-1-yl)-4R-1,2,4-triazole-3-thione derivatives for their identification and establishing a deep connection between spectra and structure of the molecule. For the studied compounds is the most characteristic absorption band in the medium wave spectrum with high values of A and f, which indicate about the permitted and probable transitions of electrons which give rise to the observed maxima. Based on the study of the basic optical characteristics of the electronic absorption spectra of 5-(adamantane-1-yl)-4R-1,2,4-triazole-3-thione derivatives is found that chromatofor in the studied molecules is the structure of 1,2,4-triazole and substituents (adamantane, methyl and phenyl radicals). A distinctive feature, namely 5-(adamantane-1-yl)-4-phenyl-1,2,4-triazole-3-thione 5-(adamantane-1-yl)-4-methyl-1,2,4-triazole-3-tion are the values A, f, Mik, which can be used to identify the investigated compounds.

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49

Sheng, Yiqi. "Enhanced blue thermally activated delayed fluorescence with rigid adamantane as non-conjugated linker for space-confined donor-acceptor charge transfer: a theoretical study." Journal of Physics: Conference Series 2338, no. 1 (September 1, 2022): 012022. http://dx.doi.org/10.1088/1742-6596/2338/1/012022.

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Abstract A lack of control over the relative orientation of donor and acceptor moieties in solid films is the main reason for poor electroluminescence efficiency found in most D-σ-A patterns. In this study, adamantane was introduced as the linker for the construction of a D-σ-A system since its rigid but non-conjugated nature. For a systematic study, the same donor (9,9-dimethyl-10-phenyl-9,10-dihydroacridine, DMTPA) and acceptor (2,4,6-triphenyl-1,3,5-triazine, TPZ) block were attached at different sites of the adamantine molecule, forming three kinds of configuration including face-to-face (FF), head-to-tail (HT), and chair (CH) style. DFT/TD-DFT simulation was carried out to investigate the electronic structures, optical characteristics, and charge transfer (ICT) properties of these three designed molecules. Attributed to a non-conjugated adamantane linker, the conjugation between donor and acceptor was disrupted for either of these molecules, resulting in high triplet energy of 2.79, 2.99, and 3.10 eV, respectively. Among them, the face-to-face style molecule presents the smallest ΔEST and greatest charge transfer excitation from donor to acceptor, suggesting an excellent potential for thermal activated delayed fluorescence (TADF). Face-to-face type molecule is a good option for a high-performance blue organic light-emitting diode (OLED) host material based on these results. Our investigation may open a door for designing new host molecule with other donor and acceptor groups to further enhance the efficiency and longevity of OLEDs.

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50

Li, Zunhua, Yingzi Tan, Manhua Ding, Linli Tang, and Fei Zeng. "Keto-Adamantane-Based Macrocycle Crystalline Supramolecular Assemblies Showing Selective Vapochromism to Tetrahydrofuran." Molecules 29, no. 3 (February 4, 2024): 719. http://dx.doi.org/10.3390/molecules29030719.

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Here, we report the synthesis of adamantane-based macrocycle 2 by combining adamantane building blocks with π-donor 1,3-dimethoxy-benzene units. An unpredictable keto-adamantane-based macrocycle 3 was obtained by the oxidation of 2 using DDQ as an oxidant. Moreover, a new type of macrocyclic molecule-based CT cocrystal was prepared through exo-wall CT interactions between 3 and DDQ. The cocrystal material showed selective vapochromism behavior towards THF, specifically, among nine volatile organic solvents commonly used in the laboratory. Powder X-ray diffraction; UV-Vis diffuse reflectance spectroscopy; 1H NMR; and single crystal X-ray diffraction analyses revealed that color changes are attributed to the vapor-triggered decomplexation of cocrystals.

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