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Journal articles on the topic 'Polyaromatic molecules'

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Author: Grafiati

Published: 11 March 2023

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1

Yazaki, Kohei, Lorenzo Catti, and Michito Yoshizawa. "Polyaromatic molecular tubes: from strategic synthesis to host functions." Chemical Communications 54, no. 26 (2018): 3195–206. http://dx.doi.org/10.1039/c8cc00799c.

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This feature article describes the recent progress in the synthesis and application of short tubular molecules bearing multiple (≥3) polyaromatic rings (e.g., anthracene, pyrene, chrysene, anthanthrenylene, and HBC). These polyaromatic tubes display characteristic properties such as strong fluorescent emission, a selective molecular binding ability, efficient host–guest energy transfer and open–closed structural transformations.

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2

He, Lanyan, Pingmei Wang, Lipeng He, Zhou Qu, Jianhui Luo, Baoliang Peng, Xianqiong Tang, and Yong Pei. "Molecular dynamics simulations of the self-organization of side-chain decorated polyaromatic conjugation molecules: phase separated lamellar and columnar structures and dispersion behaviors in toluene solvent." RSC Advances 8, no. 20 (2018): 11134–44. http://dx.doi.org/10.1039/c7ra13101a.

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3

Kartel, M. T., V. V. Lobanov, E. M. Demyanenko, Wang Bo, A. G. Grebenyuk, and O. S. Karpenko. "Sorption of molecular hydrogen on the graphene-like matrix doped by N- and B-atoms." Himia, Fizika ta Tehnologia Poverhni 12, no. 2 (June 30, 2021): 112–23. http://dx.doi.org/10.15407/hftp12.02.112.

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The regularities of interaction of hydrogen molecules with graphene-like planes, where two carbon atoms are replaced by nitrogen or boron atoms, have been studied by the methods of quantum chemistry (DFT, B3LYP, 6-31G**). To take into account the dispersion contributions to the energy of formation of intermolecular complexes that occur during the formation of adsorption supramolecular structures, Grimme’ dispersion correction is used - D3. To study the effect of the size of a graphene-like cluster on the energy of molecular hydrogen chemisorption, polyaromatic molecules (PAM) are used of pyrene, coronene and that consisting of 54 carbon atoms, as well as their nitrogen- and boron-containing analogues where N- and B-atoms are placed in a para-position relative to each other, in the so-called piperazine configuration. The insertion of a heteroatom changes the structure of the transition state and the mechanism of chemisorption. An analysis of the results of quantum chemical calculations showed the highest exothermic dissociative adsorption of the H2 molecule on B-containing graphene-like ones. For N-containing PAM, the exothermicity of the mentioned reaction is somewhat lower, for it a possibility of desorption of atomic hydrogen desorption the surface of the latter with subsequent recombination in the gas phase has been also shown. At the same time, for models of pure graphene-like layer, the data obtained indicate the impossibility of chemisorption of molecular hydrogen. Without a complete analysis of the results for all the possible locations of the pair of hydrogen atoms (formed due to dissociation of the H2 molecule) bound by nitrogen-containing polyaromatic molecules, it can be noted that the dissociative chemisorption of the H2 molecule, regardless of the nature of heteroatom in the PAM, is thermodynamically more probable at the periphery of the model molecules than that in their centers.

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4

Markevich, Alexander, Simon Kurasch, Ossi Lehtinen, Oliver Reimer, Xinliang Feng, Klaus Müllen, Andrey Turchanin, Andrei N. Khlobystov, Ute Kaiser, and Elena Besley. "Electron beam controlled covalent attachment of small organic molecules to graphene." Nanoscale 8, no. 5 (2016): 2711–19. http://dx.doi.org/10.1039/c5nr07539d.

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5

Hagiwara, Keita, Munetaka Akita, and Michito Yoshizawa. "An aqueous molecular tube with polyaromatic frameworks capable of binding fluorescent dyes." Chemical Science 6, no. 1 (2015): 259–63. http://dx.doi.org/10.1039/c4sc02377c.

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6

Thomas, Michael, Irene Suarez-Martinez, Li-Juan Yu, Amir Karton, Graham S. Chandler, Marc Robinson, Isabelle Cherchneff, Dahbia Talbi, and Dino Spagnoli. "Atomistic simulations of the aggregation of small aromatic molecules in homogenous and heterogenous mixtures." Physical Chemistry Chemical Physics 22, no. 37 (2020): 21005–14. http://dx.doi.org/10.1039/d0cp02622k.

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7

Rumi, Mariacristina, Giuseppe Zerbi, Klaus Müllen, G. Müller, and Matthias Rehahn. "Nonlinear optical and vibrational properties of conjugated polyaromatic molecules." Journal of Chemical Physics 106, no. 1 (January 1997): 24–34. http://dx.doi.org/10.1063/1.473191.

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8

Lee, Hwankyu, and Yong-Kul Lee. "Effects of the asphaltene structure and the tetralin/heptane solvent ratio on the size and shape of asphaltene aggregates." Physical Chemistry Chemical Physics 19, no. 21 (2017): 13931–40. http://dx.doi.org/10.1039/c7cp01579h.

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Asphaltene molecules, which consist of differently hydrogenated polyaromatic cores grafted with side alkyl chains of different sizes and grafting densities, were simulated with a solvent mixture of heptane and tetralin using coarse-grained force fields.

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9

Tohnai, Norimitsu, Atsushi Yamamoto, Ichiro Hisaki, and Mikiji Miyata. "Hierarchical Construction of Versatile Diamondoid Porous Organic Salts (d-POS)." Acta Crystallographica Section A Foundations and Advances 70, a1 (August 5, 2014): C983. http://dx.doi.org/10.1107/s2053273314090160.

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Porous materials using organic molecules have attracted much attention due to their potential application such as gas absorption and so on. However, it is still difficult to construct porous structures from only simple organic molecules. Thus, we proposed a novel hierarchical method to construct porous structures. In this method, the first step is to build up molecular assemblies. These assemblies act to sustain porous structures with larger inclusion spaces. Then, the assemblies are accumulated by intermolecular interactions between assemblies to achieve both robustness and dynamics of the porous structures. We have previously reported organic salts composed of triphenylmethylamine (TPMA) and various sulfonic acid derivatives constructed unique molecular assemblies "supramolecular clusters" through cubic hydrogen-bonding networks. Here we demonstrate that TPMA and sulfonic acids having polyaromatic moieties give a new class of porous structures consisting of diamond networks, named as diamondoid porous organic salts (d-POSs). The supramolecular clusters are hierarchically accumulated by π–π interactions between the polyaromatic moieties to yield the d-POSs through formation of the diamond networks. Large steric hindrance of the clusters prevents the diamond networks from constructing highly interpenetrated structures, giving continuous open channels. It should be noted that the interpenetration degree of the diamond networks is controlled by tuning the bulkiness of the cluster with alteration of sulfonic acids.

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10

Maziarz III, E. Peter, Gary A. Baker, and Troy D. Wood. "Electrospray ionization Fourier transform mass spectrometry of polycyclic aromatic hydrocarbons using silver(I)-mediated ionization." Canadian Journal of Chemistry 83, no. 11 (November 1, 2005): 1871–77. http://dx.doi.org/10.1139/v05-195.

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Here, a methodology employing doped Ag(I) salt as an in situ cationization reagent for efficient ionization of nonpolar molecules within a conventional electrospray ionization source is described. The effectiveness of Ag(I)-mediated ionization is demonstrated using ESI Fourier transform mass spectrometry for the rapid detection and identification of priority pollutant polyaromatic hydrocarbon (PAH) species. In contrast to earlier coordination ESI-MS reports employing silver salts, argentated species are not typically observed for PAH species. Instead, oxidation of the PAH occurs to produce only the [PAH]+· odd-electron molecular parent ion, simplifying spectral analysis. In addition, the method demonstrates linear quantitative performance. The Ag(I) reagent provides quantifiable PAHs (not ordinarily amenable to ESI-MS) from 64 ppb, and suggests the immediate potential for sampling and on-line monitoring of complex, real world, and otherwise intractable environmental samples. Finally, the high mass accuracy of ESI Fourier transform mass spectrometry further allows unequivocal identification of molecular formulas within PAH mixtures.Key words: electrospray ionization, nonpolar, hydrocarbons, polyaromatic, Fourier transform mass spectrometry.

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11

Ascenzi, Daniela, Julia Aysina, Paolo Tosi, Andrea Maranzana, and Glauco Tonachini. "Growth of polyaromatic molecules via ion-molecule reactions: An experimental and theoretical mechanistic study." Journal of Chemical Physics 133, no. 18 (November 14, 2010): 184308. http://dx.doi.org/10.1063/1.3505553.

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12

Ichioka, Fumiki, Yuhei Itai, Yuji Nishii, and Masahiro Miura. "Palladium-Catalyzed Direct C2-Arylation of Benzo[b]thiophenes with Electron-Rich Aryl Halides: Facile Access to Thienoacene Derivatives." Synlett 28, no. 20 (April 11, 2017): 2812–16. http://dx.doi.org/10.1055/s-0036-1588994.

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Direct coupling reaction of benzo[b]thiophene and electron-rich aryl bromides was achieved under Pd2(dba)3/SPhos catalysis in the presence of NaOt-Bu. The reaction system was applied for the installation of 2-(methylthio)phenyl group onto thiophene-fused polyaromatic molecules, demonstrating facile synthesis of precursors for thienoacene derivatives.

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13

Bulusheva, L. G., A. V. Okotrub, A. V. Gusel'nikov, D. V. Konarev, A. L. Litvinov, and R. N. Lyubovskaya. "Electronic structure of the complexes of fullerene C60 with polyaromatic molecules." Journal of Molecular Structure 648, no. 3 (March 2003): 183–89. http://dx.doi.org/10.1016/s0022-2860(03)00027-9.

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14

Peterková, Kateřina, Ivo Durník, Radek Marek, Janez Plavec, and Peter Podbevšek. "c-kit2 G-quadruplex stabilized via a covalent probe: exploring G-quartet asymmetry." Nucleic Acids Research 49, no. 15 (August 7, 2021): 8947–60. http://dx.doi.org/10.1093/nar/gkab659.

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Abstract Several sequences forming G-quadruplex are highly conserved in regulatory regions of genomes of different organisms and affect various biological processes like gene expression. Diverse G-quadruplex properties can be modulated via their interaction with small polyaromatic molecules such as pyrene. To investigate how pyrene interacts with G-rich DNAs, we incorporated deoxyuridine nucleotide(s) with a covalently attached pyrene moiety (Upy) into a model system that forms parallel G-quadruplex structures. We individually substituted terminal positions and positions in the pentaloop of the c-kit2 sequence originating from the KIT proto-oncogene with Upy and performed a detailed NMR structural study accompanied with molecular dynamic simulations. Our results showed that incorporation into the pentaloop leads to structural polymorphism and in some cases also thermal destabilization. In contrast, terminal positions were found to cause a substantial thermodynamic stabilization while preserving topology of the parent c-kit2 G-quadruplex. Thermodynamic stabilization results from π–π stacking between the polyaromatic core of the pyrene moiety and guanine nucleotides of outer G-quartets. Thanks to the prevalent overall conformation, our structures mimic the G-quadruplex found in human KIT proto-oncogene and could potentially have antiproliferative effects on cancer cells.

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15

Clark, Victoria H. J., and David M. Benoit. "The vibrational signatures of polyaromatic hydrocarbons on an ice surface." Proceedings of the International Astronomical Union 15, S350 (April 2019): 468–70. http://dx.doi.org/10.1017/s174392131900944x.

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AbstractWe use quantum chemical techniques to model the vibrational spectra of small aromatic molecules on a proton-ordered hexagonal crystalline water ice (XIh) model. We achieve a good agreement with experimental data by accounting for vibrational anharmonicity and correcting the potential energy landscape for known failures of density functional theory. A standard harmonic description of the vibrational spectra only leads to a broad qualitative agreement.

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16

Acree, William, and James S. Chickos. "Phase Transition Enthalpy Measurements of Organic Compounds. An Update of Sublimation, Vaporization, and Fusion Enthalpies from 2016 to 2021." Journal of Physical and Chemical Reference Data 51, no. 4 (December 1, 2022): 043101. http://dx.doi.org/10.1063/5.0081916.

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The compendium of phase change enthalpies published in two parts in 2016 is updated to include new fusion, vaporization, and sublimation enthalpies published in the interim and includes some earlier data either previously missed or were unavailable. Also included in this article is an update of recent studies on the phase change enthalpies of polyaromatic hydrocarbons. Group values previously evaluated to adjust for temperature of phase changes are updated for aromatic compounds in view of recent experimental data. The new group parameters have been evaluated on the basis of their consistency in providing appropriate temperature adjustments to phase change enthalpies at T = 298 K as evaluated by a thermochemical cycle. This evaluation provides transition temperatures and about 1000 heats of fusion, 700 heats of vaporization, 500 heats of sublimation, and about 50 other heats of transitions for about 30 polyaromatic hydrocarbons and 1100 other molecules consisting of C1-C57 organic compunds, organometallics, inorganic compounds, and ionic liquids taken from about 900 references.

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17

Teklebrhan, Robel B., Cuiying Jian, Phillip Choi, Zhenghe Xu, and Johan Sjöblom. "Competitive Adsorption of Naphthenic Acids and Polyaromatic Molecules at a Toluene–Water Interface." Journal of Physical Chemistry B 120, no. 50 (December 13, 2016): 12901–10. http://dx.doi.org/10.1021/acs.jpcb.6b07938.

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18

Li, Heng, Xiaoguang Xu, Jian Shang, Jianlong Li, Xinquan Hu, Boon K. Teo, and Kai Wu. "Proton-Assisted Self-Assemblies of Linear Di-Pyridyl Polyaromatic Molecules at Solid/Liquid Interface." Journal of Physical Chemistry C 116, no. 41 (October 9, 2012): 21753–61. http://dx.doi.org/10.1021/jp303352h.

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19

Kurihara, Kohei, Kohei Yazaki, Munetaka Akita, and Michito Yoshizawa. "A Switchable Open/closed Polyaromatic Macrocycle that Shows Reversible Binding of Long Hydrophilic Molecules." Angewandte Chemie International Edition 56, no. 38 (August 9, 2017): 11360–64. http://dx.doi.org/10.1002/anie.201703357.

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20

Kurihara, Kohei, Kohei Yazaki, Munetaka Akita, and Michito Yoshizawa. "A Switchable Open/closed Polyaromatic Macrocycle that Shows Reversible Binding of Long Hydrophilic Molecules." Angewandte Chemie 129, no. 38 (August 9, 2017): 11518–22. http://dx.doi.org/10.1002/ange.201703357.

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21

Campbell, Josh, and Graeme Day. "Structure prediction of N-heteroacenes as potential organic semiconductors." Acta Crystallographica Section A Foundations and Advances 70, a1 (August 5, 2014): C1621. http://dx.doi.org/10.1107/s2053273314083788.

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Organic electronics offer exciting new alternatives to traditional inorganic devices based on advantages such as lower cost, ease of manufacture and flexibility. Small molecule semiconductors such as pentacene and rubrene are the focus of intense research due to performance approaching that of inorganic semiconductors. Charge transfer in polyaromatic hydrocarbons (PAHs) relies on the degree of π-conjugation and overlap of the π-systems of neighbouring molecules in the solid state. Small changes in the intermolecular interactions can lead to important changes in crystal packing and electronic properties. Thus, functionalization of PAHs is often used to improve their packing in the solid state. The addition of electronegative atoms into the ring system of pentacene has been proposed for improving stability while retaining attractive properties. [1] N-heteroacenes result from the substitution of nitrogen into the arene ring structure. The resulting potential for weak hydrogen bonding could direct coplanar molecular arrangements, sheet formation and favourable π-overlap for charge transport. Theoretical studies [2] have been carried out showing promising properties at the molecular level. As of yet no analysis of the solid state of these molecules has been performed to investigate how this substitution affects the packing and electronic properties. Here, we present the results of crystal structure prediction studies and calculation of charge transport properties aimed at understanding the influence of nitrogen substitution on the crystal packing of N-heteropentacenes and their performance as semiconducting materials.

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22

Teklebrhan, Robel B., Lingling Ge, Subir Bhattacharjee, Zhenghe Xu, and Johan Sjöblom. "Initial Partition and Aggregation of Uncharged Polyaromatic Molecules at the Oil–Water Interface: A Molecular Dynamics Simulation Study." Journal of Physical Chemistry B 118, no. 4 (January 21, 2014): 1040–51. http://dx.doi.org/10.1021/jp407363p.

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23

Tseng, Hsiang-Han, Michele Serri, Nicholas Harrison, and Sandrine Heutz. "Properties and degradation of manganese(III) porphyrin thin films formed by high vacuum sublimation." Journal of Porphyrins and Phthalocyanines 23, no. 11n12 (December 2019): 1515–22. http://dx.doi.org/10.1142/s1088424619501700.

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Manganese porphyrins are of interest due to the optical, electronic and magnetic properties of the central metal ion, coupled to the low bandgap of the polyaromatic ring. These attractive characteristics are harnessed in solutions or in ultra-thin films, such as, for example, self-assembled monolayers. However, for devices, thicker films deposited using a controlled and reproducible method are required. Here we present the morphological, structural, chemical and optical properties of manganese(III) tetraphenylporphyrin chloride (MnTPPCl) thin films deposited using organic molecular beam deposition, typically employed to process analogue molecules for applications such as organic photovoltaics. We find, using a combination of UV-vis and X-ray photoelectron spectroscopies, that the sublimation process leads to the scission of the Mn–Cl bond. The resultant film is a Mn(II)TPP:Mn(III)TPPCl blend where approximately half the molecules have been reduced. Following growth, exposure to air oxidizes the Mn(II)TPP molecule. Through quantitative analysis of the time-dependent optical properties, the oxygen diffusion coefficient (D) [Formula: see text] is obtained, corresponding to a slow bulk oxidation following fast oxidation of a 8-nm-thick surface layer. The bulk diffusion D is lower than for analogous polycrystalline films, suggestion that grain boundaries, rather than molecular packing, are the rate-limiting steps in oxidation of molecular films. Our results highlight that the stability of the axial ligands should be considered when depositing metal porphyrins from the vapor phase, and offer a solvent-free route to obtain reproducible and smooth thin films of complex materials for engineering film functionalities.

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24

Kahkhaie, V. Rezaie, M. H. Yousefi, M. Darbani, and A. Mobashery. "Application of Fe-graphene oxide nanocomposite to improve SERS intensity of polyaromatic hydrocarbons-=SUP=-*-=/SUP=-." Журнал технической физики 127, no. 11 (2019): 827. http://dx.doi.org/10.21883/os.2019.11.48522.36-19.

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Abstract Raman spectroscopy is used to provide a structural finger-print by which molecules can be identified. SERS technique offers many orders of magnitude enhancement in initial weak Raman signal of some molecules. To detect Raman signal of pyrene, magnetic properties of iron nanoparticles (Fe NPs) was employed along with graphene oxide (GO). Significant differences were discovered in performance of five different SERS substrates which were prepared using magnetized and non-magnetized Fe NPs-GO nanocomposites (FNRC) and Ag nanoparticles. UV-Vis, Raman and FE-SEM analysis presented complete formation of Ag-NPs, GO and FNRCs. The quantity of enhancement measured showed different enhancements from 1.09 up to 3.54 times for pyrene solution on magnetized Fe NP-GO nanocomposite. SERS enhancement showed a reverse relation with GO/Fe precursor rate. Raman shift suggested formation of new bonds. 2.017 RSD factor presented very fast performance only 10 seconds after irradiation of magnetized FNRCs.

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25

Godlewski, Szymon, Marek Kolmer, Mads Engelund, Hiroyo Kawai, Rafal Zuzak, Aran Garcia-Lekue, Mark Saeys, et al. "Interaction of a conjugated polyaromatic molecule with a single dangling bond quantum dot on a hydrogenated semiconductor." Physical Chemistry Chemical Physics 18, no. 5 (2016): 3854–61. http://dx.doi.org/10.1039/c5cp07307c.

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26

Basova, Tamara V., and Maxim S. Polyakov. "Hybrid Materials Based on Carbon Nanotubes and Polyaromatic Molecules: Methods of Functionalization and Sensor Properties." Macroheterocycles 13, no. 2 (2020): 91–112. http://dx.doi.org/10.6060/mhc200710b.

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27

Rossich Molina, Estefania, and Tamar Stein. "The Effect of Cluster Size on the Intra-Cluster Ionic Polymerization Process." Molecules 26, no. 16 (August 7, 2021): 4782. http://dx.doi.org/10.3390/molecules26164782.

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Polyaromatic hydrocarbons (PAHs) are widespread in the interstellar medium (ISM). The abundance and relevance of PAHs call for a clear understanding of their formation mechanisms, which, to date, have not been completely deciphered. Of particular interest is the formation of benzene, the basic building block of PAHs. It has been shown that the ionization of neutral clusters can lead to an intra-cluster ionic polymerization process that results in molecular growth. Ab-initio molecular dynamics (AIMD) studies in clusters consisting of 3–6 units of acetylene modeling ionization events under ISM conditions have shown maximum aggregation of three acetylene molecules forming bonded C6H6+ species; the larger the number of acetylene molecules, the higher the production of C6H6+. These results lead to the question of whether clusters larger than those studied thus far promote aggregation beyond three acetylene units and whether larger clusters can result in higher C6H6+ production. In this study, we report results from AIMD simulations modeling the ionization of 10 and 20 acetylene clusters. The simulations show aggregation of up to four acetylene units producing bonded C8H8+. Interestingly, C8H8+ bicyclic species were identified, setting a precedent for their astrochemical identification. Comparable reactivity rates were shown with 10 and 20 acetylene clusters.

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28

Malatong, Ruttapol, Wijitra Waengdongbung, Phattananawee Nalaoh, Nuttapong Chantanop, Pongsakorn Chasing, Chokchai Kaiyasuan, Suangsiri Arunlimsawat, Taweesak Sudyoadsuk, and Vinich Promarak. "Deep-Blue Triplet–Triplet Annihilation Organic Light-Emitting Diode (CIEy ≈ 0.05) Using Tetraphenylimidazole and Benzonitrile Functionalized Anthracene/Chrysene Emitters." Molecules 27, no. 24 (December 15, 2022): 8923. http://dx.doi.org/10.3390/molecules27248923.

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Herein, new deep-blue triplet-triplet annihilation (TTA) molecules, namely 4-(10-(4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenyl)anthracen-9-yl)benzonitrile (TPIAnCN) and 4-(12-(4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenyl)chrysen-6-yl)benzonitrile (TPIChCN), are designed, synthesized, and investigated as emitters for organic light-emitting diodes (OLED). TPIAnCN and TPIChCN are composed of polyaromatic hydrocarbons of anthracene (An) and chrysene (Ch) as the cores functionalized with tetraphenylimidazole (TPI) and benzonitrile (CN) moieties, respectively. The experimental and theoretical results verify their excellent thermal properties, photophysical properties, as well as electrochemical properties. Particularly, their emissions are in the deep blue region, with TTA emissions being observed in their thin films. By utilization of these molecules as emitters, deep blue TTA OLEDs with CIE coordinates of (0.15, 0.05), high external quantum efficiency of 6.84%, and high exciton utilization efficiency (ηs) of 48% were fabricated. This result manifests the potential use of chrysene as an alternate building block to formulate new TTA molecules for accomplishing high-performance TTA OLEDs.

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Nikovskiy, Igor A., Kseniya L. Isakovskaya, and Yulia V. Nelyubina. "New Low-Dimensional Hybrid Perovskitoids Based on Lead Bromide with Organic Cations from Charge-Transfer Complexes." Crystals 11, no. 11 (November 21, 2021): 1424. http://dx.doi.org/10.3390/cryst11111424.

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We have obtained a series of low-dimensional hybrid perovskitoids (often referred to as perovskites) based on lead bromide. As organic cations, the derivatives of polyaromatic and conjugated molecules, such as anthracene, pyrene and (E)-stilbene, were chosen to form charge-transfer complexes with various organic acceptors for use as highly tunable components of hybrid perovskite solar cells. X-ray diffraction analysis showed these crystalline materials to be new 1D- and pseudo-layered 0D-perovskitoids with lead bromide octahedra featuring different sharing modes, such as in unusual mini-rods of four face- and edge-shared octahedra. Thanks to the low dimensionality, they can be of use in another type of optoelectronic device, photodetectors.

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Yang, Yuanyuan, Xiaoyi Hu, Deping Zhang, Weiwei Zhang, Guilin Liu, and Junfeng Zhen. "Laboratory formation and photochemistry of covalently bonded polycyclic aromatic nitrogen heterocycle (PANH) clusters in the gas phase." Monthly Notices of the Royal Astronomical Society 498, no. 1 (July 29, 2020): 1–11. http://dx.doi.org/10.1093/mnras/staa2212.

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ABSTRACT To examine the evolution processes of the nitrogen-containing polycyclic aromatic hydrocarbon (PAH) molecules occurring in interstellar environments, in this work we focus on the formation of large covalently bonded N-substituted polyaromatic species and their photochemistry behaviour in the gas phase. The experimental results show large PANH (e.g. DC/acridine and DC/phenazine) cluster cations formed in a chemical reaction between large PAH (e.g. dicoronylene, DC, C48H20) cations and small PANHs (e.g. acridine, C13H9N, or phenazine, C12H8N2) by gas-phase condensation through ion–molecule reactions. With laser irradiation, PANH cluster cations are involved in a complex photofragmentation process (e.g. dehydrogenation, HCN/CN, C2 or N2 units lost) and then form large PANH/PAH or multiple dehydrogenated molecules; in particular, the dehydrogenation of PANH clusters provides a possible way to synthesize large nitrogen-containing graphene species (e.g. C59N+ and C61N+). Also, we perform quantum-theoretical calculations on the formation and photochemistry of DC/acridine and DC/phenazine cluster cations: two types of molecular cluster are considered (C–C and C–N bond type) and the formation pathway and dissociation energy for each isomer are determined. The experimental and theoretical findings obtained give a general molecular growth pathway toward all-benzenoid aromatic species with size (> 60 C atoms) in the astrophysically relevant range, during a ground-up formation process, and offer understanding of the nitrogen element effect on their chemical-evolutionary behaviour. Also, studies of DC/acridine and DC/phenazine clusters (89–112 atoms, ∼2 nm in size) offer a feasible means of explanation for the formation of nanoscale dust grains (nitrogen element included) in space.

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31

Monsen, Robert C., Jon M. Maguire, Lynn W. DeLeeuw, Jonathan B. Chaires, and John O. Trent. "Drug discovery of small molecules targeting the higher-order hTERT promoter G-quadruplex." PLOS ONE 17, no. 6 (June 16, 2022): e0270165. http://dx.doi.org/10.1371/journal.pone.0270165.

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DNA G-quadruplexes (G4s) are now widely accepted as viable targets in the pursuit of anticancer therapeutics. To date, few small molecules have been identified that exhibit selectivity for G4s over alternative forms of DNA, such as the ubiquitous duplex. We posit that the lack of current ligand specificity arises for multiple reasons: G4 atomic models are often small, monomeric, single quadruplex structures with few or no druggable pockets; targeting G-tetrad faces frequently results in the enrichment of extended electron-deficient polyaromatic end-pasting scaffolds; and virtual drug discovery efforts often under-sample chemical search space. We show that by addressing these issues we can enrich for non-standard molecular templates that exhibit high selectivity towards G4s over other forms of DNA. We performed an extensive virtual screen against the higher-order hTERT core promoter G4 that we have previously characterized, targeting 12 of its unique loop and groove pockets using libraries containing 40 million drug-like compounds for each screen. Using our drug discovery funnel approach, which utilizes high-throughput fluorescence thermal shift assay (FTSA) screens, microscale thermophoresis (MST), and orthogonal biophysical methods, we have identified multiple unique G4 binding scaffolds. We subsequently used two rounds of catalogue-based SAR to increase the affinity of a disubstituted 2-aminoethyl-quinazoline that stabilizes the higher-order hTERT G-quadruplex by binding across its G4 junctional sites. We show selectivity of its binding affinity towards hTERT is virtually unaffected in the presence of near-physiological levels of duplex DNA, and that this molecule downregulates hTERT transcription in breast cancer cells.

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32

Astafan, Amir, Alexander Sachse, Catherine Batiot-Dupeyrat, and Ludovic Pinard. "Impact of the Framework Type on the Regeneration of Coked Zeolites by Non-Thermal Plasma in a Fixed Bed Dielectric Barrier Reactor." Catalysts 9, no. 12 (November 24, 2019): 985. http://dx.doi.org/10.3390/catal9120985.

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The formation of coke as a result of propene transformation at 623 K on zeolites results from a product shape selectivity mechanism of which the products are polyaromatic molecules, such as pyrene on MFI, anthracene on MOR, pyrene and coronene on FAU. Zeolite regeneration can be achieved by using non-thermal plasma (NTP), with decreased energy consumption, employing a fixed bed dielectric barrier reactor. The efficiency of this alternative regeneration process depends on the coke toxicity. On MFI and FAU (featuring three-dimensional 10 and 12 ring channel systems, respectively) coking occurs by poisoning the Brønsted acid sites; on MOR, (presenting a one-dimensional 12 ring channel system) pore blocking takes place, leading to higher coke toxicity. A complete coke removal is achieved on MFI and FAU zeolites using NTP within 3 h, while for MOR coke, removal proceeds slower and is incomplete after 3 h on stream. Hence, the efficiency of regeneration is impacted by the accessibility of active oxygenated species generated under plasma (e.g., O*, O2+) to coke molecules.

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Tchoń, Daniel, and Anna Makal. "Structure and piezochromism of pyrene-1-carbaldehyde at high pressure." Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 75, no. 3 (May 17, 2019): 343–53. http://dx.doi.org/10.1107/s2052520619003354.

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The crystal structure of pyrene-1-carbaldehyde (PA), a model polyaromatic hydrocarbon, highly luminescent in the solid state and crystallizing in the triclinic system, has been re-determined at several pressures ranging from atmospheric up to 3 GPa using a diamond anvil cell. A `multi-crystal' approach was used in crystal structure determination, significantly improving completeness of X-ray diffraction data attainable for such a low-symmetry system. The crystal structure consists of infinite π-stacks of PA molecules with discernible dimers, which resemble aggregates formed by pyrene derivatives in solution as well as in the solid state. A series of measurements showed that the average inter-planar distance between individual molecules within π-stacks decreases with pressure in the investigated range. This results in piezochromic properties of PA: a significant sample color change as well as a red-shift of fluorescence with pressure, as studied with UV–vis spectroscopy. Periodic DFT calculations allowed us to relate the variations in the crystal structure with pressure to the changes in the electronic structure of this material.

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Hofto, Laura R., Karina Van Sickle, and Mauricio Cafiero. "Modeling intercalation through the sandwich-type interactions between benzene and 14 polyaromatic molecules: DFT andab initio results." International Journal of Quantum Chemistry 108, no. 1 (2007): 112–18. http://dx.doi.org/10.1002/qua.21426.

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Agrup, Sara, and Marcus Aldén. "Measurements of the Collisionally Quenched Lifetime of CO in Hydrocarbon Flames." Applied Spectroscopy 48, no. 9 (September 1994): 1118–24. http://dx.doi.org/10.1366/0003702944029514.

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Time-resolved laser-induced fluorescence (LIF) from CO molecules in hydrocarbon flames was studied. Collisional quenching constants were evaluated on the basis of the exponential decays. Effective lifetime in a methane/oxygen flame was observed to vary between 250 and 400 ps depending on the position within the flame, and from 400 to 600 ps in the non-sooty parts of an ethylene/air flame. Fluorescence, constituting simultaneous spatially and temporally resolved decays, was also registered from various sections along a laser beam that probed different parts of the flame. Spectral recordings revealed not only the expected CO peaks but also, in the ethylene flame, laser-induced emission from C2 Swan bands and from polyaromatic hydrocarbon (PAH) emission that affected the fluorescence time decay in the sooty part of the flame.

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Rano, Madhumita, Sumanta K. Ghosh, and Debashree Ghosh. "In the quest for a stable triplet state in small polyaromatic hydrocarbons: an in silico tool for rational design and prediction." Chemical Science 10, no. 40 (2019): 9270–76. http://dx.doi.org/10.1039/c9sc02414j.

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Qian, Kuangnan, Kathleen E. Edwards, and Mike Siskin. "Characterization of Large Nonvolatile Polyaromatic Molecules by a Combination of In-Source Pyrolysis and Field Desorption Mass Spectrometry." Energy & Fuels 15, no. 4 (July 2001): 949–54. http://dx.doi.org/10.1021/ef010023e.

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Bhattacharya, Sumanta, Kalyan Ghosh, Shrabanti Banerjee, and Manas Banerjee. "Energies of charge transfer and formation equilibria of the complexes of [70]fullerene with some interesting polyaromatic molecules." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 64, no. 1 (May 2006): 47–53. http://dx.doi.org/10.1016/j.saa.2005.06.036.

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Palermo, Vincenzo, Susanna Morelli, Matteo Palma, Christopher Simpson, Fabian Nolde, Andreas Herrmann, Klaus Müllen, and Paolo Samorì. "Nanoscale Structural and Electronic Properties of Ultrathin Blends of Two Polyaromatic Molecules: A Kelvin Probe Force Microscopy Investigation." ChemPhysChem 7, no. 4 (March 10, 2006): 847–53. http://dx.doi.org/10.1002/cphc.200500480.

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Lim, Hee Nam, Wan Pyo Hong, and Inji Shin. "1,4-Azaborines: Origin, Modern Synthesis, and Applications as Optoelectronic Materials." Synthesis 54, no. 03 (November 4, 2021): 570–88. http://dx.doi.org/10.1055/s-0040-1719851.

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AbstractThis short review summarizes the origins and recent progress in 1,4-azaborine research, focusing on synthetic methodologies. Academic laboratories have made significant efforts to generate boron-nitrogen-containing heteroaromatic compounds that mimic arenes. 1,2-, 1,3-, and 1,4-Azaborine motifs have provided breakthrough molecules in applications ranging from medicines to materials. Owing to recent advances in polyaromatic 1,4-azaborine synthesis and applications in industry, the research field is currently undergoing a renaissance. Photo- and electroluminescent properties driven by distinct structural variations are key components in the design of novel 1,4-azaborine structures. In this review, seminal reports on the synthesis of simple 1,4-azaborines to complex π-extended structures are briefly highlighted together along with key optoelectronic properties.1 Introduction2 Non-Fused 1,4-Azaborines3 Monobenzo-Fused 1,4-Azaborines4 Dibenzo-Fused 1,4-Azaborines and Their Derivatives5 Ladder-Type 1,4-Azaborines6 Complex 1,4-Azaborines7 Optoelectronic Properties of Key 1,4-Azaborines8 Conclusion and Outlook

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Dejonghe, S., R. Hubaut, T. Des Courieres, and J. Grimblot. "Influence of the competitive adsorption of polyaromatic and vanadylporphyrin molecules on the deactivation of a Ni-MoS2-Al2O3 catalyst." Applied Catalysis 61, no. 1 (May 1990): L9—L14. http://dx.doi.org/10.1016/s0166-9834(00)82129-6.

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Sevrioukova, Irina F. "Crystal Structure of CYP3A4 Complexed with Fluorol Identifies the Substrate Access Channel as a High-Affinity Ligand Binding Site." International Journal of Molecular Sciences 23, no. 20 (October 20, 2022): 12591. http://dx.doi.org/10.3390/ijms232012591.

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Cytochrome P450 3A4 (CYP3A4) is a major human drug-metabolizing enzyme, notoriously known for its extreme substrate promiscuity, allosteric behavior, and implications in drug–drug interactions. Despite extensive investigations, the mechanism of ligand binding to CYP3A4 is not fully understood. We determined the crystal structure of CYP3A4 complexed with fluorol, a small fluorescent dye that can undergo hydroxylation. In the structure, fluorol associates to the substrate channel, well suited for the binding of planar polyaromatic molecules bearing polar groups, through which stabilizing H-bonds with the polar channel residues, such as Thr224 and Arg372, can be established. Mutagenesis, spectral, kinetic, and functional data confirmed the involvement but not strict requirement of Thr224 for the association of fluorol. Collectively, our data identify the substrate channel as a high-affinity ligand binding site and support the notion that hydrophobic ligands first dock to the nearby peripheral surface, before migrating to the channel and, subsequently, into the active site.

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Brackmann, Christian, Zhongshan Li, Martin Rupinski, Nicolas Docquier, Gaelle Pengloan, and Marcus Aldén. "Strategies for Formaldehyde Detection in Flames and Engines Using a Single-Mode Nd:YAG/OPO Laser System." Applied Spectroscopy 59, no. 6 (June 2005): 763–68. http://dx.doi.org/10.1366/0003702054280748.

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This paper presents technical developments for the detection of formaldehyde (CH2O) using laser-induced fluorescence. The easily accessible third harmonic of the Nd:YAG laser at 355 nm was used for excitation of formaldehyde. In order to investigate potential background fluorescence, e.g., from large molecules such as polyaromatic hydrocarbons, special attention was paid to investigating the possibility of scanning the wavelength of a single-mode Nd:YAG laser under the gain profile, ∼3 cm−1, on and off resonance. Furthermore, a technique for simultaneous detection of formaldehyde and OH using one laser system is presented. The single-mode Nd: YAG laser at 355 nm in combination with an optical parametric oscillator (OPO) laser tuned to 283 nm was used for simultaneous two-dimensional imaging of both species using one charge-coupled device (CCD) detector equipped with a dual filter image separator. The techniques are demonstrated with measurements in laboratory flames and the combined measurements are also demonstrated in an engine.

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Guttmann, Robin, Johannes Hoja, Christoph Lechner, Reinhard J. Maurer, and Alexander F. Sax. "Adhesion, forces and the stability of interfaces." Beilstein Journal of Organic Chemistry 15 (January 11, 2019): 106–29. http://dx.doi.org/10.3762/bjoc.15.12.

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Weak molecular interactions (WMI) are responsible for processes such as physisorption; they are essential for the structure and stability of interfaces, and for bulk properties of liquids and molecular crystals. The dispersion interaction is one of the four basic interactions types – electrostatics, induction, dispersion and exchange repulsion – of which all WMIs are composed. The fact that each class of basic interactions covers a wide range explains the large variety of WMIs. To some of them, special names are assigned, such as hydrogen bonding or hydrophobic interactions. In chemistry, these WMIs are frequently used as if they were basic interaction types. For a long time, dispersion was largely ignored in chemistry, attractive intermolecular interactions were nearly exclusively attributed to electrostatic interactions. We discuss the importance of dispersion interactions for the stabilization in systems that are traditionally explained in terms of the “special interactions” mentioned above. System stabilization can be explained by using interaction energies, or by attractive forces between the interacting subsystems; in the case of stabilizing WMIs, one frequently speaks of adhesion energies and adhesive forces. We show that the description of system stability using maximum adhesive forces and the description using adhesion energies are not equivalent. The systems discussed are polyaromatic molecules adsorbed to graphene and carbon nanotubes; dimers of alcohols and amines; cellulose crystals; and alcohols adsorbed onto cellulose surfaces.

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Honda, Akiko, Ken-ichiro Inoue, Shin Tamura, Michitaka Tanaka, Zaoshi Wang, Toshio Tanaka, Seitarou Hirai, Tomoaki Okuda, Kayo Ueda, and Hirohisa Takano. "Effects of Streamer Discharge on PM2.5 Containing Endotoxins and Polyaromatic Hydrocarbons and Their Biological Responses In Vitro." International Journal of Molecular Sciences 23, no. 24 (December 14, 2022): 15891. http://dx.doi.org/10.3390/ijms232415891.

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Experimental and epidemiological studies have demonstrated that fine particulate matter with a diameter of <2.5 μm (PM2.5) affects both the respiratory and immune systems. However, effective approaches to reduce PM2.5-induced hazardous effects have not been discovered yet. Streamer discharge is a category of plasma discharge in which high-speed electrons collide with oxygen and nitrogen molecules. Although streamer discharge can reportedly eliminate bacteria, molds, chemical substances, and allergens, its ability to decontaminate PM2.5 has not been previously demonstrated. The present study explored whether streamer discharge treatment could reduce PM2.5-induced inflammatory responses by employing an in vitro system. PM2.5 was collected under four conditions (Bangkok (Sep.–Dec.), Bangkok (Dec.–Mar.), Singapore, and Taipei). Airway epithelial cells and antigen-presenting cells exposed to non-treated PM2.5 in several conditions resulted in inflammatory responses. Streamer-discharged PM2.5 (Bangkok (Sep.–Dec.)) decreased the expression of interleukin (IL)-6 and IL-8 compared to non-treated PM2.5. Moreover, composition analysis demonstrated that streamer discharge reduced some compounds, such as endotoxins and polycyclic aromatic hydrocarbons, included in PM2.5 that can elicit inflammatory responses. Streamer discharge treatment can reduce endotoxins, polycyclic aromatic hydrocarbons, and the subsequent inflammatory responses induced by PM2.5 in vitro.

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Yarosh, E. V., E. V. Larina, N. A. Lagoda, A. A. Kurokhtina, and A. F. Schmidt. "Polyaromatic Products of Three-Component Coupling of Aryl Halide with Two Molecules of Arylacetylene and Arylboronic Acid under Ligand-Free Catalysis Conditions." Russian Journal of Organic Chemistry 55, no. 5 (May 2019): 678–81. http://dx.doi.org/10.1134/s1070428019050154.

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Islam, Md Monarul, Paris E. Georghiou, Shofiur Rahman, and Takehiko Yamato. "Calix[3]arene-Analogous Metacyclophanes: Synthesis, Structures and Properties with Infinite Potential." Molecules 25, no. 18 (September 14, 2020): 4202. http://dx.doi.org/10.3390/molecules25184202.

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Calixarene-analogous metacyclophanes (CAMs) are a special class of cyclophanes that are cyclic polyaromatic hydrocarbons containing three or more aromatic rings linked by one or more methylene bridging groups. They can be considered to be analogues of calixarenes, since, in both types of molecules, the component aromatic rings are linked by methylene groups, which are meta to each other. Since the prototype or classical calix[4]arene consists of four benzene rings each linked by methylene bridges, which are also meta to each other, it can be considered to be an example of a functionalized [1.1.1.1]metacyclophane. A metacyclophane (MCP) that consists of three individual hydroxyl-group functionalized aromatic rings linked by methylene groups, e.g., a trihydroxy[1.1.1]MCP may therefore, by analogy, be termed in the broadest sense as a “calix[3]arene” or a “calix[3]arene-analogous metacyclophane”. Most of the CAMs reported have been synthesized by fragment coupling approaches. The design, synthesis and development of functionalized CAMs, MCPs, calixarenes and calixarene analogues has been an area of great activity in the past few decades, due their potential applications as molecular receptors, sensors and ligands for metal binding, and for theoretical studies, etc. In this review article, we focus mainly on the synthesis, structure and conformational properties of [1.1.1]CAMs, i.e., “calix[3]arenes” and their analogues, which contain three functionalized aromatic rings and which provide new scaffolds for further explorations in supramolecular and sensor chemistry.

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Tan, Wen, Fan Yang, Tingting Yi, Gang Liu, Xiaoting Wei, Qiurong Long, Yi Liu, et al. "Fullerene-like elastic carbon coatings on silicon nanoparticles by solvent controlled association of natural polyaromatic molecules as high-performance lithium-ion battery anodes." Energy Storage Materials 45 (March 2022): 412–21. http://dx.doi.org/10.1016/j.ensm.2021.11.040.

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Borzdun, Natalia, Artyom Glova, Sergey Larin, and Sergey Lyulin. "Influence of Asphaltene Modification on Structure of P3HT/Asphaltene Blends: Molecular Dynamics Simulations." Nanomaterials 12, no. 16 (August 20, 2022): 2867. http://dx.doi.org/10.3390/nano12162867.

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Further development and commercialization of bulk heterojunction (BHJ) solar cells require the search for novel low-cost materials. The present study addresses the relations between the asphaltenes’ chemical structure and the morphology of the poly(3-hexylthiohene) (P3HT)/asphaltene blends as potential materials for the design of BHJ solar cells. By means of all-atom molecular dynamics simulations, the formation of heterophase morphology is observed for the P3HT-based blends with carboxyl-containing asphaltenes, as well as the aggregation of the asphaltenes into highly ordered stacks. Although the π–π interactions between the polyaromatic cores of the asphaltenes in solutions are sufficient for the molecules to aggregate into ordered stacks, in a blend with a conjugated polymer, additional stabilizing factors are required, such as hydrogen bonding between carboxyl groups. It is found that the asphaltenes’ aliphatic side groups may improve significantly the miscibility between the polymer and the asphaltenes, thereby preventing the formation of heterophase morphology. The results also demonstrate that the carboxyl-containing asphaltenes/P3HT ratio should be at least 1:1, as a decrease in concentration of the asphaltenes leads to the folding of the polymer chains, lower ordering in the polymer phase and the destruction of the interpenetrating 3D structure formed by P3HT and the asphaltene phases. Overall, the results of the present study for the first time reveal the aggregation behavior of the asphaltenes of varying chemical structures in P3HT, as well the influence of their presence and concentration on the polymer phase structure and blend morphology, paving the way for future development of BHJ solar cells based on the conjugated polymer/asphaltene blends.

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Hagiwara, Keita, Masafumi Otsuki, Munetaka Akita, and Michito Yoshizawa. "Polyaromatic molecular tubes with a subnanometer pore and the guest-induced emission enhancement behavior." Chemical Communications 51, no. 52 (2015): 10451–54. http://dx.doi.org/10.1039/c5cc02931g.

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