Towards the Making of [12]Collarene

Ashton, Peter R.; Isaacs, Neil S.; Kohnke, Franz H.; Slawin, Alexandra M. Z.; Spencer, Catriona M.; Stoddart, J. Fraser; Williams, David J.

doi:10.1002/anie.198809661

Cited by 138 publications

(73 citation statements)

References 13 publications

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“…There have been reports of the systems in which -orbitals are oriented vertically to the plane of the rings, namely belt-shape carbocyclic-conjugated systems (such as annulenes, beltenes, cyclacenes, and collarenes) (28)(29)(30)(31)(32)(33)(34)(35)(36)(37). The recent discoveries of fully conjugated systems with a curved surface like fullerenes and carbon nanotubes (38,39) further adds fuel to such a kind of study.…”

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Ionophores and receptors using cation-π interactions: Collarenes

Choi

Suh

Cho

et al. 1998

Proc. Natl. Acad. Sci. U.S.A.

153

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Cation-interactions are important forces in molecular recognition by biological receptors, enzyme catalysis, and crystal engineering. We have harnessed these interactions in designing molecular systems with circular arrangement of benzene units that are capable of acting as ionophores and models for biological receptors.[n]Collarenes are promising candidates with high selectivity for a specific cation, depending on n, because of their structural rigidity and well-defined cavity size. [12]Collarene exhibits a pronounced affinity for tetramethylammonium cation and acetylcholine, which implies that it could serve as a model for acetylcholinestrase. Thus, collarenes can prove to be novel and effective ionophores͞model-receptors capable of heralding a new direction in molecular recognition and host-guest chemistry.The design of novel ionophores and receptors has attracted considerable interest in the recent past (1-5). The cationinteraction discovered by Dougherty and coworkers (6, 7) has received much attention as a new type of binding force important in biological molecular recognition (8-15), enzyme catalysis (16, 17), and crystal engineering (3, 18). This cationinteraction is known to be responsible for the binding of acetylcholine (ACh) to its deactivating enzyme (8, 9), acetylcholinestrase (19,20), which has served as a target receptor in designing therapeutic agents against various ailments like myasthenia gravis, glaucoma, and Alzheimer's disease (21-23).A lot of effort and concern has been evinced on the disposal of nuclear wastes. A major bottleneck, however, stems from the effective separation of major hazardous isotopes (such as 137 Cs and 90 Sr, which have fairly long half-lives of Ϸ30 years) from these wastes (24-27). There have been extensive attempts to design and develop systems that can be used in nuclear waste separations as effective ionophores. In this context the use of various types of ionophores has been reported (25-27), and there have been extensive attempts to explore new types of ionophores that have a high selectivity for these hazardous isotopes.It therefore is appealing to investigate the possibility of designing novel ionophores and model receptors based on the principle of the cation-interaction. There have been reports of the systems in which -orbitals are oriented vertically to the plane of the rings, namely belt-shape carbocyclic-conjugated systems (such as annulenes, beltenes, cyclacenes, and collarenes) (28-37). The recent discoveries of fully conjugated systems with a curved surface like fullerenes and carbon nanotubes (38, 39) further adds fuel to such a kind of study. However, belt-shape carbocyclic-conjugated systems have hardly been studied apart from the synthetic study of cyclacene precursors and collarenes (32-37).Thus, it would be of importance to investigate whether cyclacenes (comprised of only benzene moieties) and collarenes (having CH 2 linkages between benzene units) can behave as ionophores and receptors. These molecular structures can be understood f...

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confidence: 99%

“…The recent discoveries of fully conjugated systems with a curved surface like fullerenes and carbon nanotubes (38,39) further adds fuel to such a kind of study. However, belt-shape carbocyclic-conjugated systems have hardly been studied apart from the synthetic study of cyclacene precursors and collarenes (32)(33)(34)(35)(36)(37).…”

mentioning

confidence: 99%

Ionophores and receptors using cation-π interactions: Collarenes

Choi

Suh

Cho

et al. 1998

Proc. Natl. Acad. Sci. U.S.A.

153

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“…[117] Sehr viel weniger erfolgreich gestaltete sich die Synthese von [n]-Cyclacenen, die Fragmente von Zickzack-CNTs repräsentieren. Gemeinsames Problem bei der Herstellung von Derivaten der [n]-Cyclacene durch die Gruppen um Schlüter, [118] Stoddart [119,120] und Cory [121,122] war die ausbleibende finale Aromatisierung der vielversprechenden partiell gesättigten Vorstufenmolekü-le. [112] Theoretische Studien weisen darauf hin, dass die stabilisierende Aromatisierungsenergie im Falle der [n]-Cyclacene nicht ausreicht, um die hohe Ringspannung zu kompensieren.…”

Section: Synthese Von Fullerenfragmenten Aromatischen Gürteln Und "Uunclassified

Nanostrukturierte Kohlenstoffmaterialien aus molekularen Vorstufen

et al. 2010

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Nanostrukturierte Kohlenstoffmaterialien, also Kohlenstoffe, die eine charakteristische Größe im Nanometerbereich sowie eine eventuell funktionalisierte Oberfläche aufweisen, spielen eine zentrale Rolle in vielen wissenschaftlichen Disziplinen. Erste Anwendungen finden derartige Materialien dabei unter anderem in Bereichen wie der Erforschung alternativer Energiequellen, leistungsfähiger Energiespeichermaterialien, nachhaltiger chemischer Technologien oder auch im Gebiet der organisch‐elektronischen Materialien. Des Weiteren könnten diese Materialien mögliche Ansätze und Lösungen bieten, um dem voranschreitenden Verbrauch fossiler Brennstoffe und somit dem Klimawandel entgegenzusteuern. Ferner könnten nanostrukturierte Kohlenstoffmaterialien auch auf dem Gebiet der Mikroelektronik einen Durchbruch herbeiführen. Allerdings ist die Entwicklung neuer Herstellungsverfahren für kohlenstoffreiche Materialien unabdingbar, die unter anderem Kontrolle über die Oberflächenchemie, die mesoskopische Struktur und die Mikrostruktur ermöglichen. Ein vielversprechender Ansatz ist dabei die Synthese dieser Materialien aus wohldefinierten molekularen Vorstufen.

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“…6 The trivial name, corannulene which was originally used by Lawton for compound (1) was later on redefined' including compounds in which not every inncr carbon is bound directly to an outer carbon atom such as (2). Although, they are not widely accepted, some other methods of nomenclature for corannuJenes and related systems are available in the literature (c.g., coronaphenes, circulenes, etc.…”

Section: Introductionmentioning

confidence: 99%

On the Cryptoannulenic Behavior of Certain Corannulenes

Türker¹

1996

Polycyclic Aromatic Compounds

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Towards the Making of [12]Collarene

Cited by 138 publications

References 13 publications

Ionophores and receptors using cation-π interactions: Collarenes

Ionophores and receptors using cation-π interactions: Collarenes

Nanostrukturierte Kohlenstoffmaterialien aus molekularen Vorstufen

On the Cryptoannulenic Behavior of Certain Corannulenes

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