Synthetic receptors: a modular approach to large structures

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Abstract

Combination of medium-sized building blocks comprises a new strategy for the synthesis of artificial receptor molecules. These building blocks should have relatively rigid structures to which functional groups can be attached, such as calix[4]- and -[6]arenes, resorcin[4]arenes, porphyrins, and cyclodextrins. Combination of a (3- cyclodextrin with a calix[4]arene moiety resulted in water soluble receptor molecules. Large multifunctional receptors have been prepared by the covalent combination of two calix[4]arenes and one Zn-tetraarylporphyrin. The controlled conformation of p-tert-butylcalix[6]arenes which are alternately substituted with methoxy groups, was used to synthesize a cryptocalix[6]arene consisting of a calix[6]arene and a cyclotriveratrylene unit. A new type of diastereoisomerism (carceroisomerism) was found during the synthesis of carceplexes constructed from one calix[4]arene and one resorcin[4]arene. In a (2+2)-mode of coupling, the combination of calix[4]arenes and resorcin[4]arenes gave a large rigid receptor molecule of nanosize dimensions (ho/and). The combination of two calix[4]arenes with one resorcin[4)arene resulted in three different compounds (endo-endo, endo-exo, and exo-exo) with large hydrophobic surfaces to which steroids can be complexed.
Original languageEnglish
Title of host publicationCrystallography of Supramolecular Compounds
EditorsGeorges Tsoucaris, Jerry L. Atwood, Janusz Lipkowski
Place of PublicationDordrecht
PublisherKluwer Academic Publishers
Pages347-368
ISBN (Print)978-0-7923-4051-5, 978-94-010-7258-8
Publication statusPublished - 1996

Publication series

NameNATO ASI Series, Series C: Mathematical and Physical Sciences
PublisherKluwer Academic Publishers
Volume480
ISSN (Print)1389-2185

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