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Articles de revues sur le sujet « Cavitandi »

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Auteur : Grafiati
Publié le 11 mars 2023

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1

Shi, Qixun, Matthew P. Mower, Donna G. Blackmond et Julius Rebek. « Water-soluble cavitands promote hydrolyses of long-chain diesters ». Proceedings of the National Academy of Sciences 113, no 33 (1 août 2016) : 9199–203. http://dx.doi.org/10.1073/pnas.1610006113.

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Water-soluble, deep cavitands serve as chaperones of long-chain diesters for their selective hydrolysis in aqueous solution. The cavitands bind the diesters in rapidly exchanging, folded J-shape conformations that bury the hydrocarbon chain and expose each ester group in turn to the aqueous medium. The acid hydrolyses in the presence of the cavitand result in enhanced yields of monoacid monoester products. Product distributions indicate a two- to fourfold relative decrease in the hydrolysis rate constant of the second ester caused by the confined space in the cavitand. The rate constant for the first acid hydrolysis step is enhanced approximately 10-fold in the presence of the cavitand, compared with control reactions of the molecules in bulk solution. Hydrolysis under basic conditions (saponification) with the cavitand gave >90% yields of the corresponding monoesters. Under basic conditions the cavitand complex of the monoanion precipitates from solution and prevents further reaction.
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2

Turunen, Lotta, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras et Kari Rissanen. « Halogen-bonded solvates of tetrahaloethynyl cavitands ». CrystEngComm 19, no 35 (2017) : 5223–29. http://dx.doi.org/10.1039/c7ce01118k.

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Tetrahaloethynyl cavitands as multitopic halogen bond donors form a multitude of solvate structures with halogen bond acceptor solvents, such as DMF and DMSO, depending on the structure of the cavitand and the nucleophilicity of the solvent used.
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3

Brekalo, Deliz, Kane, Friščić et Holman. « Exploring the Scope of Macrocyclic “Shoe-last” Templates in the Mechanochemical Synthesis of RHO Topology Zeolitic Imidazolate Frameworks (ZIFs) ». Molecules 25, no 3 (1 février 2020) : 633. http://dx.doi.org/10.3390/molecules25030633.

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The macrocyclic cavitand MeMeCH2 is used as a template for the mechanochemical synthesis of 0.2MeMeCH2@RHO-Zn16(Cl2Im)32 (0.2MeMeCH2@ZIF-71) and RHO-ZnBIm2 (ZIF-11) zeolitic imidazolate frameworks (ZIFs). It is shown that MeMeCH2 significantly accelerates the mechanochemical synthesis, providing high porosity products (BET surface areas of 1140 m2/g and 869 m2/g, respectively). Templation of RHO-topology ZIF frameworks constructed of linkers larger than benzimidazole (HBIm) was unsuccessful. It is also shown that cavitands other than MeMeCH2—namely MeHCH2, MeiBuCH2, HPhCH2, MePhCH2, BrPhCH2, BrC5CH2—can serve as effective templates for the synthesis of x(cavitand)@RHO-ZnIm2 products. The limitations on cavitand size and shape are explored in terms of their effectiveness as templates.
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4

Pedrini, Alessandro, Federico Bertani et Enrico Dalcanale. « Fluorinated Tetraphosphonate Cavitands ». Molecules 23, no 10 (17 octobre 2018) : 2670. http://dx.doi.org/10.3390/molecules23102670.

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Two synthetic protocols for the introduction of fluorine atoms into resorcinarene-based cavitands, at the lower and upper rim, respectively, are reported. Cavitand 1, bearing four fluorocarbon tails, and cavitand 2, which presents a fluorine atom on the para position of a diester phosphonate phenyl substituent, were synthesized and their complexation abilities toward the model guest sarcosine methyl ester hydrochloride were evaluated via NMR titration experiments. The effect of complexation on the 19F NMR resonance of the probe is evident only in the case of cavitand 2, where the inset of the cation-dipole and H-bonding interactions between the P=O bridges and the guest is reflected in a sizable downfield shift of the fluorine probe.
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5

Turunen, L., N. K. Beyeh, F. Pan, A. Valkonen et K. Rissanen. « Tetraiodoethynyl resorcinarene cavitands as multivalent halogen bond donors ». Chem. Commun. 50, no 100 (2014) : 15920–23. http://dx.doi.org/10.1039/c4cc07771g.

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The first examples of iodoethynyl resorcinarene cavitands as rigid 3D halogen bond (XB) donor molecules are presented. These concave macrocycles form strong, RXB = 0.78–0.83, halogen bonds with dioxane oxygen, pyridine nitrogen and a bromide anion in tetraproropyl ammonium bromide resulting in deep cavity cavitand structures.
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6

Dalcanale, E., M. Torelli, I. Domenichelli, A. Pedrini, F. Guagnini, R. Pinalli, F. Terenziani, F. Artoni et R. Brighenti. « pH-Driven Conformational Switching of Quinoxaline Cavitands in Polymer Matrices ». Synlett 29, no 19 (24 juillet 2018) : 2503–8. http://dx.doi.org/10.1055/s-0037-1610219.

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While pH-driven interconversion of tetraquinoxaline cavitands (QxCav) from vase to kite conformation has been extensively studied both in solution and at interfaces, cavitands behavior in solid matrices is still unexplored. Therefore, the synthesis of a new class of quinoxaline cavitand based copolymers is here reported; a soluble linear poly(butyl methacrylate) (PBMA) and an insoluble cross-linked polydimethylsiloxane (PDMS), ensuring a convenient incorporation of the switchable unit, were chosen as polymer matrices. Conformational studies, performed both in solution and at the solid state, confirmed the retention of vase → kite switching behavior when moving from monomeric units to polymeric structures.
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7

Pinalli, Roberta, et Chiara Massera. « Nitrosonium complexation by the tetraphosphonate cavitand 5,11,17,23-tetramethyl-6,10:12,16:18,22:24,4-tetrakis(phenylphosphonato-κ2O,O)resorcin(4)arene ». Acta Crystallographica Section E Crystallographic Communications 73, no 12 (3 novembre 2017) : 1801–5. http://dx.doi.org/10.1107/s2056989017015857.

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The crystal structure of a new supramolecular complex between the tetraphosphonate cavitand 5,11,17,23-tetramethyl-6,10:12,16:18,22:24,4-tetrakis(phenylphosphonato-κ2O,O′)resorcin(4)arene and the nitrosyl cation NO+, as the BF4−salt, is reported. The complex, of general formula [(C56H44P4O12)(NO)]BF4·CH2Cl2or NO@Tiiii[H, CH3, C6H5] BF4·CH2Cl2, crystallizes in the space groupP-1. The nitrosyl cation is disordered over two equivalent positions, with occupancies of 0.503 (2) and 0.497 (2), and interacts with two adjacent P=O groups at the upper rim of the cavitand through dipole–charge interactions. In the lattice, the cavitands are connected through a series of C—H...π interactions involving the methyl and methylenic H atoms and the aromatic rings of the macrocycle. The structure is further stabilized by the presence of C—H...F interactions between the hydrogen atoms of the cavitands and the F atoms of the tetrafluoridoborate anion. As a result of the disorder, the lattice dichloromethane molecules could not be modelled in terms of atomic sites, and were treated using thePLATONSQUEEZE procedure [Spek (2015).Acta Cryst.C71, 9–18]. The complexation process has also been studied in solution through NMR titrations.
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8

Rahman, Faiz-Ur, Yong-sheng Li, Ioannis D. Petsalakis, Giannoula Theodorakopoulos, Julius Rebek et Yang Yu. « Recognition with metallo cavitands ». Proceedings of the National Academy of Sciences 116, no 36 (19 août 2019) : 17648–53. http://dx.doi.org/10.1073/pnas.1909154116.

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We describe here the effects of metal complexation on the molecular recognition behavior of cavitands with quinoxaline walls. The nitrogen atoms of the quinoxalines are near the upper rim of the vase-like shape and treatment with Pd(II) gave 2:1 metal:cavitand derivatives. Characterization by 1H, 13C NMR spectroscopy, HR ESI-MS, and computations showed that the metals bridged adjacent quinoxaline panels and gave cavitands with C2v symmetry. Both water-soluble and organic-soluble versions were prepared and their host/guest complexes with alkanes, alcohols, acids, and diols (up to C12) were studied by 1H NMR spectroscopy. Analysis of the binding behavior indicated that the metals rigidified the walls of the receptive vase conformation and enhanced the binding of hydrophobic and even water-soluble guests, compared to related cavitands reported previously. The results demonstrated that the conformational dynamics of the cavitand were slowed by the coordination of Pd(II) and stabilized the host’s complexes.
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9

Biavardi, Elisa, et Chiara Massera. « Crystal structure of a host–guest complex between mephedrone hydrochloride and a tetraphosphonate cavitand ». Acta Crystallographica Section E Crystallographic Communications 75, no 2 (29 janvier 2019) : 277–83. http://dx.doi.org/10.1107/s2056989019001464.

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A new supramolecular complex (I) between the tetraphosphonate cavitand Tiiii[C3H7,CH3,C6H5] [systematic name: 2,8,14,20-tetrapropyl-5,11,17,23-tetramethyl-6,10:12,16:18,22:24,4-tetrakis(phenylphosphonato-O,O′)resorcin[4]arene] and mephedrone hydrochoride {C11H16NO+·Cl−; systematic name: methyl[1-(4-methylphenyl)-1-oxopropan-2-yl]azanium chloride} has been obtained and characterized both in solution and in the solid state. The complex of general formula (C11H16NO)@Tiiii[C3H7,CH3,C6H5]Cl·CH3OH or C11H16NO+·Cl−·C68H68O12P4·CH3OH, crystallizes in the monoclinic space group P21/c with one lattice methanol molecule per cavitand, disordered over two positions with occupancy factors of 0.665 (6) and 0.335 (6). The mephedrone guest interacts with the P=O groups at the upper rim of the cavitand through two charge-assisted N—H...O hydrogen bonds, while the methyl group directly bound to the amino moiety is stabilized inside the π basic cavity via cation...π interactions. The chloride counter-anion is located between the alkyl legs of the cavitand, forming C—H...Cl interactions with the aromatic and methylenic H atoms of the lower rim. The chloride anion is also responsible for the formation of a supramolecular chain along the b-axis direction through C—H...Cl interactions involving the phenyl substituent of one phosphonate group. C—H...O and C—H...π interactions between the guest and adjacent cavitands contribute to the formation of the crystal structure.
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10

Pedrini, Alessandro. « Host–guest supramolecular interactions between a resorcinarene-based cavitand bearing a –COOH moiety and acetic acid ». Acta Crystallographica Section E Crystallographic Communications 75, no 3 (22 février 2019) : 397–401. http://dx.doi.org/10.1107/s2056989019002512.

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The cavitand 5,11,17,23-tetramethyl-4,24:6,10:12,16:18,22-tetrakis(methylenedioxy)resorcin[4]arene functionalized at the upper rim with a carboxylic acid group, CavCOOH-in, of chemical formula C37H32O10, was synthesized in order to study its supramolecular interactions with acetic acid in the solid state. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a dichloromethane–acetone solution of CavCOOH-in, to which glacial acetic acid had been added. The resulting compound, C37H32O10·2C2H4O2 (1) crystallizes in the space group P\overline{1} and its asymmetric unit consists of one molecule of cavitand and two molecules of acetic acid, one of which is encapsulated inside the aromatic cavity and disordered over two positions with a refined occupancy ratio of 0.344 (4):0.656 (4). The guest interacts with the host primarily through its methyl group, which (in both orientations) forms C—H...π interactions with the benzene rings of the cavitand. The crystal structure of 1 is dominated by O—H...O and C—H...O hydrogen bonding due to the presence of acetic acid and of the carboxylic group functionalizing the upper rim. Further stabilization is provided by offset π–π stacking interactions between the aromatic walls of adjacent cavitands [intercentroid distance = 3.573 (1) Å].
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11

Haino, Takeharu, Ryo Sekiya, Kentaro Harada et Natsumi Nitta. « Resorcinarene-Based Supramolecular Capsules : Supramolecular Functions and Applications ». Synlett 33, no 06 (27 octobre 2021) : 518–30. http://dx.doi.org/10.1055/a-1679-8141.

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AbstractA resorcinarene is a synthetic macrocycle consisting of four resorcinol molecules covalently linked by methylene bridges. The interannular bridges produce a cavitand that has a bowl-shaped structure. We have developed supramolecular capsules through Ag(I) or Cu(I) coordination-driven self-assembly of cavitands possessing 2,2′-bipyridyl arms in their upper rims. The self-assembled capsules accommodate various molecular guests and supramolecular assemblies possessing acetoxy groups. The host–guest chemistry of the molecular capsules has been applied in the fabrication of supramolecular polymers. This account describes recent developments in the supramolecular chemistry of resorcinarene-based coordination capsules and provides a brief history of resorcinarene-based capsules and related capsules.
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12

Santonocito, Rossella, Nunzio Tuccitto, Andrea Pappalardo et Giuseppe Trusso Sfrazzetto. « Smartphone-Based Dopamine Detection by Fluorescent Supramolecular Sensor ». Molecules 27, no 21 (3 novembre 2022) : 7503. http://dx.doi.org/10.3390/molecules27217503.

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Supramolecular recognition of dopamine by two quinoxaline cavitands was studied in solution by fluorescence titrations, ESI-MS and ROESY measurements. In addition, the tetraquinoxaline cavitand was dropped onto a siloxane-based polymeric solid support, obtaining a sensor able to detect dopamine in a linear range of concentrations 10 Mm–100 pM, with a detection limit of 1 pM, much lower than the normal concentration values in the common human fluids (plasma, urine and saliva), by using a simple smartphone as detector. This sensor shows also good selectivity for dopamine respect to the other common analytes contained in a saliva sample and can be reused after acid–base cycles, paving the way for the realization of real practical sensor for human dopamine detection.
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13

Naumann, Christoph, Esteban Román, Carlos Peinador, Tong Ren, Brian O. Patrick, Angel E. Kaifer et John C. Sherman. « Expanding Cavitand Chemistry : The Preparation and Characterization of [n]Cavitands withn≥4 ». Chemistry 7, no 8 (17 avril 2001) : 1637–45. http://dx.doi.org/10.1002/1521-3765(20010417)7:8<1637 ::aid-chem16370>3.0.co;2-x.

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14

Hamada, Fumio, Shigeki Ito, Miyuki Narita et Norio Nashirozawa. « Selective chloromethylation of cavitand at the upper rim and induced fit type complexation with metal cations by new cavitands : Aza-crown-modified cavitands ». Tetrahedron Letters 40, no 8 (février 1999) : 1527–30. http://dx.doi.org/10.1016/s0040-4039(98)02702-6.

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15

Boerrigter, Harold, Willem Verboom, Gerrit J. van Hummel, Sybolt Harkema et David N. Reinhoudt. « Selective functionalization of resorcinarene cavitands ; Single crystal X-ray structure of a distally functionalized cavitand ». Tetrahedron Letters 37, no 29 (juillet 1996) : 5167–70. http://dx.doi.org/10.1016/0040-4039(96)01027-1.

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16

Wishard, Anthony, et Bruce C. Gibb. « Dynamic light scattering studies of the effects of salts on the diffusivity of cationic and anionic cavitands ». Beilstein Journal of Organic Chemistry 14 (23 août 2018) : 2212–19. http://dx.doi.org/10.3762/bjoc.14.195.

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Although alkali halide salts play key roles in all living systems, the physical models used to describe the properties of aqueous solutions of salts do not take into account specific ion–ion interactions. To identify specific ion–ion interactions possibly contributing to the aggregation of proteins, we have used dynamic light scattering (DLS) to probe the aggregation of charged cavitands. DLS measurements of negatively charged 1 in the presence of a range of alkali metal halides reveal no significant aggregation of host 1 as a function of the nature of the cation of the added salt. Only at high concentrations could trace amounts of aggregation be detected by 1H NMR spectroscopy. Contrarily, 1 was readily aggregated and precipitated by ZnCl2. In contrast, although fluoride and chloride did not induce aggregation of positively charged host 2, this cavitand exhibited marked aggregation as a function of bromide and iodide concentration. Specifically, bromide induced small but significant amounts of dimerization, whilst iodide induced extreme aggregation. Moreover, in these cases aggregation of host 2 also exhibited a cationic dependence, with an observed trend Na+ > Li+ > K+ ≈ Cs+. In combination, these results reveal new details of specific ion pairings in aqueous solution and how this can influence the properties of dissolved organics.
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17

Lagauzere, Muriel, et Jean Pierre Franc. « La nouvelle veine d'essais du tunnel hydrodynamique du LEGI ». La Houille Blanche, no 4 (août 2018) : 73–76. http://dx.doi.org/10.1051/lhb/2018044.

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Cette note présente les principaux choix techniques réalisés à l'occasion de la rénovation récente de l'une des veines d'essais du tunnel hydrodynamique du Laboratoire des Ecoulements Géophysiques et Industriels de Grenoble. Après une brève description du nouveau circuit hydraulique, le dispositif de supervision des conditions de fonctionnement de l'installation est présenté. Le profil à tester, monté dans la veine d'essais, est piloté en incidence par un moteur brushless permettant de lui communiquer une loi quelconque de variation d'incidence en fonction du temps. Ce dispositif offre une grande flexibilité et ouvre des perspectives nouvelles en matière de recherche sur les écoulements cavitants instationnaires. Un système d'acquisition haute fréquence a été également développé afin d'acquérir en simultané les signaux d'une matrice de capteurs de pression PVDF miniatures équipant le profil d'essais. Ce type de mesure est particulièrement adapté à l'évaluation du potentiel érosif d'un écoulement cavitant. L'acquisition des signaux est synchronisée à l'acquisition d'images par vidéo rapide afin de corréler pressions instationnaires et structures de vapeur et permettre ainsi l'interprétation des signaux de pression.
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18

Kobayashi, Mutsumi, Mei Takatsuka, Ryo Sekiya et Takeharu Haino. « Molecular recognition of upper rim functionalized cavitand and its unique dimeric capsule in the solid state ». Organic & ; Biomolecular Chemistry 13, no 6 (2015) : 1647–53. http://dx.doi.org/10.1039/c4ob02251c.

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Calix[4]resorcinarene-based cavitand recognized the methyl group of the guests to form 1 : 1 host–guest complexes. In the solid state, the cavitand formed a dimeric capsule in which two molecules of nitromethane were entrapped by weak noncovalent interactions.
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Janosi, Tibor Zoltan, Jouko Korppi-Tommola, Zsolt Csok, Laszlo Kollar, Pasi Myllyperkio et Janos Erostyak. « Anthracene Fluorescence Quenching by a Tetrakis (Ketocarboxamide) Cavitand ». Journal of Spectroscopy 2014 (2014) : 1–8. http://dx.doi.org/10.1155/2014/708739.

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Quenching of both fluorescence lifetime and fluorescence intensity of anthracene was investigated in the presence of a newly derived tetrakis (ketocarboxamide) cavitand at various concentrations. Time-correlated single photon counting method was applied for the lifetime measurements. A clear correlation between the fluorescence lifetime of anthracene as a function of cavitand concentration in dimethylformamide solution was observed. The bimolecular collisional quenching constant was derived from the decrease of lifetime. Fluorescence intensity was measured in the emission wavelength region around 400 nm as a result of excitation at 280 nm. Effective quenching was observed in the presence of the cavitand. The obtained Stern-Volmer plot displayed upward curvature. The results did not follow even extended Stern-Volmer behavior, often used to describe deviations from static bimolecular quenching. To explain our results we adopted the Smoluchowski model and obtained a reasonable estimate for the molecular radius of the cavitand in solution.
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20

Wan, Yun-Hui, Yu-Jie Zhu, Julius Rebek et Yang Yu. « Recognition of Hydrophilic Cyclic Compounds by a Water-Soluble Cavitand ». Molecules 26, no 7 (30 mars 2021) : 1922. http://dx.doi.org/10.3390/molecules26071922.

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A water-soluble deep cavitand bearing amides on the upper rim and trimethyl ammonium groups on the feet was synthesized. The open-ended cavity is stabilized by the intramolecular hydrogen bonds formed between the adjacent amides, and the introduction of trimethylammonium imparts to the cavitand good solubility in water. The cavitand exhibits high binding affinity and selectivity to hydrophilic molecules in water. With certain guests, such as cyclohexyl alcohols, amines and acids, the recognition involves the synergistic action of hydrogen bonding with hydrophobic effects. The binding phenomena are interpreted in terms of a fixed solvent cage presented by the host to the guest.
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21

Tucci, Fabio C., Dmitry M. Rudkevich et Julius Rebek. « Deeper Cavitands ». Journal of Organic Chemistry 64, no 12 (juin 1999) : 4555–59. http://dx.doi.org/10.1021/jo990209z.

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22

Rudkevich, Dmitry M., et Julius Rebek, Jr. « Deepening Cavitands ». European Journal of Organic Chemistry 1999, no 9 (septembre 1999) : 1991–2005. http://dx.doi.org/10.1002/(sici)1099-0690(199909)1999:9<1991 ::aid-ejoc1991>3.0.co;2-5.

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23

Starnes, Stephen D., Dmitry M. Rudkevich et Julius Rebek. « Cavitand−Porphyrins ». Journal of the American Chemical Society 123, no 20 (mai 2001) : 4659–69. http://dx.doi.org/10.1021/ja010038r.

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24

Dumoulin, Fabienne, Derya Topkaya, Songül Yaşar, Vefa Ahsen et Ümit İşci. « Covalent or supramolecular combinations of resorcinarenes and porphyrinoids ». Journal of Porphyrins and Phthalocyanines 20, no 05 (mai 2016) : 571–81. http://dx.doi.org/10.1142/s108842461630010x.

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Cavitands and porphyrinoids are two major groups of molecules. If cyclodextrins are maybe the most famous type of cavitands, the properties of resorcinarenes are now well known and rise rapidly increasing attention. This mini-review aims at detailing all the combinations of resorcinarenes with porphyrinoids reported so far, evidencing the bright future of such combos. In addition, two newly synthesized porphyrins-resorcinarene hybrids are reported.
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25

Havlík, Martin, Václav Parchaňský, Petr Bouř, Vladimír Král et Bohumil Dolensky. « Bridged bis-Tröger’s base molecular tweezers as new cavitand family ». Collection of Czechoslovak Chemical Communications 74, no 7-8 (2009) : 1091–99. http://dx.doi.org/10.1135/cccc2009036.

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New molecular tweezers based on bis-Tröger’s base with methoxycarbonyl groups on its pincers was prepared. These groups were converted into hydroxymethyl groups, which were interconnected by a linker to give the bridged molecular tweezers, a cavitand. The cavitand was studied and its ability to bind nitrobenzene was compared with similar bis-Tröger’s base molecular tweezers.
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26

Brancatelli, Giovanna, Enrico Dalcanale, Roberta Pinalli et Silvano Geremia. « Probing the Structural Determinants of Amino Acid Recognition : X-Ray Studies of Crystalline Ditopic Host-Guest Complexes of the Positively Charged Amino Acids, Arg, Lys, and His with a Cavitand Molecule ». Molecules 23, no 12 (19 décembre 2018) : 3368. http://dx.doi.org/10.3390/molecules23123368.

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Crystallization of tetraphosphonate cavitand Tiiii[H, CH3, CH3] in the presence of positively charged amino acids, namely arginine, lysine, or histidine, afforded host-guest complex structures. The X-ray structure determination revealed that in all three structures, the fully protonated form of the amino acid is ditopically complexed by two tetraphosphonate cavitand molecules. Guanidinium, ammonium, and imidazolium cationic groups of the amino acid side chain are hosted in the cavity of a phosphonate receptor, and are held in place by specific hydrogen bonding interactions with the P=O groups of the cavitand molecule. In all three structures, the positively charged α-ammonium groups form H-bonds with the P=O groups, and with a water molecule hosted in the cavity of a second tetraphosphonate molecule. Furthermore, water-assisted dimerization was observed for the cavitand/histidine ditopic complex. In this 4:2 supramolecular complex, a bridged water molecule is held by two carboxylic acid groups of the dimerized amino acid. The structural information obtained on the geometrical constrains necessary for the possible encapsulation of the amino acids are important for the rational design of devices for analytical and medical applications.
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27

Mosca, Simone, Dariush Ajami et Julius Rebek. « Recognition and sequestration of ω-fatty acids by a cavitand receptor ». Proceedings of the National Academy of Sciences 112, no 36 (24 août 2015) : 11181–86. http://dx.doi.org/10.1073/pnas.1515233112.

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One of the largest driving forces for molecular association in aqueous solution is the hydrophobic effect, and many synthetic receptors with hydrophobic interiors have been devised for molecular recognition studies in water. Attempts to create the longer, narrower cavities appropriate for long-chain fatty acids have been thwarted by solvophobic collapse of the synthetic receptors, giving structures that have no internal spaces. The collapse generally involves the stacking of aromatic panels onto themselves. We describe here the synthesis and application of a deep cavitand receptor featuring “prestacked” aromatic panels at the upper rim of the binding pocket. The cavitand remains open and readily sequesters biologically relevant long-chain molecules—unsaturated ω-3, -6, and -9 fatty acids and derivatives such as anandamide—from aqueous media. The cavitand exists in isomeric forms with different stacking geometries and n-alkanes were used to characterize the binding modes and conformational properties. Long alkyl chains are accommodated in inverted J-shaped conformations. An analogous cavitand with electron-rich aromatic walls was prepared and comparative binding experiments indicated the role of intramolecular stacking in the binding properties of these deep container molecules.
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Sumby, Christopher J., Julie Fisher, Timothy J. Prior et Michaele J. Hardie. « Tris(pyridylmethylamino)cyclotriguaiacylene Cavitands : An Investigation of the Solution and Solid-State Behaviour of Metallo-Supramolecular Cages and Cavitand-Based Coordination Polymers ». Chemistry - A European Journal 12, no 11 (3 avril 2006) : 2945–59. http://dx.doi.org/10.1002/chem.200501542.

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Kiss, László, Zoltán Nagymihály, Péter Szabó, László Kollár et Sándor Kunsági-Máté. « Anodic Polymerization of Phenylphenols in Methyl Isobutyl Ketone and Mesityl Oxide : Incorporation of a Cavitand into the Layers Formed for Sensing Phenols in Organic Media ». Molecules 27, no 17 (23 août 2022) : 5366. http://dx.doi.org/10.3390/molecules27175366.

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The electropolymerization of three phenylphenol isomers was studied in methyl isobutyl ketone and mesityl oxide, and the remarkable differences highlighted the importance of the carbon–carbon double bond in mesityl oxide. In the case of each substrate, a brownish deposit formed during the electrooxidation. The obvious difference between the polymers formed from the two solvents was recognized via voltammetric signal enhancement of 4-methoxyphenol and 4-chlorophenol, and it was only observed in the case of mesityl oxide. The experiments highlighted that incorporation of a cavitand with biphenyl groups on the upper rim of the polymers of phenylphenols improved the results to a small extent. The cavitand was, itself, electroactive without any fouling effect. As 2-phenylphenol is by far the cheapest of the three isomers, a cavitand was incorporated into its polymer, which was exploited to solve analytical problems while mesityl oxide was used as solvent. Useful quantifications were achieved in organic solvents; however, it failed under aqueous conditions due to the high hydrophobicity of the deposit. Application of differential pulse voltammetry for 4-methoxyphenol and 4-chlorophenol gave detection limits of 9.28 and 50.8 μM in acetonitrile, respectively. This procedure resulted in the immobilization of cavitand derivatives onto the electrode’s surface, and the layer formed offered selective sensing of phenols by electrochemical methods.
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30

Sliwa, Wanda, et Jerzy Peszke. « Chemistry of Cavitands ». Mini-Reviews in Organic Chemistry 4, no 2 (1 mai 2007) : 125–42. http://dx.doi.org/10.2174/157019307780599306.

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Rudkevich, Dmitry M., Göran Hilmersson et Julius Rebek. « Self-Folding Cavitands ». Journal of the American Chemical Society 120, no 47 (décembre 1998) : 12216–25. http://dx.doi.org/10.1021/ja982970g.

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Renslo, Adam R., Dmitry M. Rudkevich et Julius Rebek. « Self-Complementary Cavitands ». Journal of the American Chemical Society 121, no 32 (août 1999) : 7459–60. http://dx.doi.org/10.1021/ja991537j.

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Ogoshi, T., Y. Nakamoto, S. Kanai, S. Fujinami et T. Yamagishi. « Pillar-Shaped Cavitands ». Synfacts 2008, no 7 (juillet 2008) : 0709. http://dx.doi.org/10.1055/s-2008-1077809.

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Mann, Enrique, et Julius Rebek. « Deepened chiral cavitands ». Tetrahedron 64, no 36 (septembre 2008) : 8484–87. http://dx.doi.org/10.1016/j.tet.2008.05.136.

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35

Sorrell, Thomas N., et Joseph L. Richards. « Selectively Difunctionalized Cavitands ». Synlett 1992, no 02 (1992) : 155–56. http://dx.doi.org/10.1055/s-1992-21300.

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36

Far, Adel Rafai, Alexander Shivanyuk et Julius Rebek. « Water-Stabilized Cavitands ». Journal of the American Chemical Society 124, no 12 (mars 2002) : 2854–55. http://dx.doi.org/10.1021/ja012453p.

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Irwin, Jacob L., David J. Sinclair, Alison J. Edwards et Michael S. Sherburn. « Chiral Conjoined Cavitands ». Australian Journal of Chemistry 57, no 4 (2004) : 339. http://dx.doi.org/10.1071/ch03299.

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Tetrabromocavitand bowls are converted into rim-connected hexabromodimers in one step in 17–22% yields by oxidative coupling of higher order arylcuprates. 1H NMR and single crystal X-ray analyses of the rim-connected dimers reveal a conformationally restricted structure in which the rims of the two cavitand bowls describe planes angled at 78.8° to one another. Each of the two bowl cavities are occupied by a guest, in addition to being partially occluded by a portion of the complementary bowl rim. These new host compounds exhibit a very unusual form of enantioisomerism.
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38

Verboom, Willem. « ChemInform Abstract : Cavitands ». ChemInform 33, no 16 (22 mai 2010) : no. http://dx.doi.org/10.1002/chin.200216260.

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Kiss, László, Zoltán Nagymihály, László Kollár et Sándor Kunsági-Máté. « Voltammetric and Fluorimetric Studies of Dibenzoylmethane on Glassy Carbon Electrodes and Its Interaction with Tetrakis (3,5-Dicarboxyphenoxy) Cavitand Derivative ». Molecules 28, no 1 (26 décembre 2022) : 185. http://dx.doi.org/10.3390/molecules28010185.

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Due to the medical importance of dibenzoylmethane, one of the aims of the study was to find an appropriate packing material and a biologically friendly co-solvent to help its introduction into living systems. Accordingly, redox properties of dibenzoylmethane were investigated on glassy carbon electrodes in acetonitrile and in 1-propanol with cyclic voltammetry, and showed a diffusion-controlled process. In the anodic window, an oxidation peak appeared at around 1.9 V in both solvents. Cycling repeatedly between 0 and 2 V, the reproducibility of this peak was acceptable, but when extending the window to higher potentials, the electrode deactivated, obviously due to electrode material. The addition of the investigated tetrakis(3,5-dicarboxyphenoxy) cavitand did not significantly change the voltammograms. Further electrochemical experiments showed that the coexistence of water in acetonitrile and 1-propanol drastically reduces the solubility of dibenzoylmethane. Moreover, very rapid electrode deactivation occurred and this fact made the use of electrochemical methods complicated. Considering that both the cavitand and dibenzoylmethane are soluble in dimethyl sulfoxide, the interaction of these species was investigated and formation of stable complexes was detected. This observation was verified with fluorescence quenching studies. The mixture of water and dimethyl sulphoxide also dramatically improved the solubility of the cavitand–dibenzoylmethane complex at high excess of water. The addition of cavitand improved the solubility of dibenzoylmethane, a property which supports the application of dibenzoylmethane in therapy.
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Pinalli, Roberta, Jakub W. Trzciński, Enrico Dalcanale et Chiara Massera. « A new, deep quinoxaline-based cavitand receptor for the complexation of benzene ». Acta Crystallographica Section E Crystallographic Communications 75, no 2 (4 janvier 2019) : 103–8. http://dx.doi.org/10.1107/s2056989018017784.

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We report the synthesis of a new macrocyclic receptor, namely 2,8,14,20-tetrahexyl-4,24:6,10:12,16:18,22-O,O′-tetrakis[2,3-dihydro-[1,4]dioxino[2,3-g]quinoxalin-7,8-diyl]resorcin[4]arene, DeepQxCav, obtained by the addition of ethylene glycol ditosylate to an octahydroxy quinoxaline cavitand. A 1:1 supramolecular complex of this cavitand with benzene has been obtained and analysed through X-ray diffraction analysis. The complex, of general formula C92H88O16N8·C6H6, crystallizes in the space group C2/c, with the cavitand host located about a twofold rotation axis. The benzene guest, which is held inside the cavity by C—H...π interactions and dispersion forces, is disordered over two equivalent sites, one in a general position and one lying on a twofold axis. The crystal structure features C—H...O hydrogen bonds and C—H...π interactions involving the alkyl chains, the aromatic rings, and the O atoms of the dioxane moiety of the resorcinarene scaffold. The crystal studied was refined as a two-component twin.
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Lin, Jing-Xiang, Yu-Xi Chen, Dan Zhao, Yu Chen, Xiu-Qiang Lu, Jian Lü et Rong Cao. « Controlled nitrite anion encapsulation and release in the molecular cavity of decamethylcucurbit[5]uril : solution and solid state studies ». Inorganic Chemistry Frontiers 6, no 1 (2019) : 303–8. http://dx.doi.org/10.1039/c8qi01168k.

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Ihm, Chaesang, et Kyungsoo Paek. « Hetero dimer from tetrakisammonium cavitand and tetratopic crown ether cavitand ». Tetrahedron Letters 48, no 18 (avril 2007) : 3263–66. http://dx.doi.org/10.1016/j.tetlet.2007.03.005.

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Yu, Yang, Yong-Sheng Li et Julius Rebek. « Binding of alkyl halides in water-soluble cavitands with urea rims ». New Journal of Chemistry 42, no 12 (2018) : 9945–48. http://dx.doi.org/10.1039/c8nj01567h.

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Nissink, J. Willem M., Harold Boerrigter, Willem Verboom, David N. Reinhoudt et John H. van der Maas. « An infrared study of host–guest association in solution by substituted resorcinarene cavitands. Part I. Structural aspects of halide complexation by a tetraurea cavitand ». Journal of the Chemical Society, Perkin Transactions 2, no 11 (1998) : 2541–46. http://dx.doi.org/10.1039/a802783h.

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Gavette, Jesse V., Kang-Da Zhang, Dariush Ajami et Julius Rebek. « Folded alkyl chains in water-soluble capsules and cavitands ». Org. Biomol. Chem. 12, no 34 (2014) : 6561–63. http://dx.doi.org/10.1039/c4ob01032a.

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Liang, Rongzu, Dongdong Bu, Xiaoshi Su, Xin Wei, Edvinas Orentas, Julius Rebek et Qixun Shi. « Organic pollutants in water-soluble cavitands and capsules : contortions of molecules in nanospace ». Organic Chemistry Frontiers 9, no 7 (2022) : 1890–96. http://dx.doi.org/10.1039/d2qo00139j.

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Kobayashi, Kenji, et Masamichi Yamanaka. « Self-assembled capsules based on tetrafunctionalized calix[4]resorcinarene cavitands ». Chemical Society Reviews 44, no 2 (2015) : 449–66. http://dx.doi.org/10.1039/c4cs00153b.

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Murray, James, Kimoon Kim, Tomoki Ogoshi, Wei Yao et Bruce C. Gibb. « The aqueous supramolecular chemistry of cucurbit[n]urils, pillar[n]arenes and deep-cavity cavitands ». Chemical Society Reviews 46, no 9 (2017) : 2479–96. http://dx.doi.org/10.1039/c7cs00095b.

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Zhang, Kang-Da, Dariush Ajami, Jesse V. Gavette et Julius Rebek. « Complexation of alkyl groups and ghrelin in a deep, water-soluble cavitand ». Chem. Commun. 50, no 38 (2014) : 4895–97. http://dx.doi.org/10.1039/c4cc01643b.

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Grajda, M., M. J. Lewińska et A. Szumna. « The templation effect as a driving force for the self-assembly of hydrogen-bonded peptidic capsules in competitive media ». Organic & ; Biomolecular Chemistry 15, no 40 (2017) : 8513–17. http://dx.doi.org/10.1039/c7ob01925d.

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