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Synthesis of elongated cavitands via click reactions and their use as chemosensors

Csók, Zsolt and Kégl, Tímea and Li, Yin and Skoda-Földes, Rita and Kiss, László and Kunsági-Máté, Sándor and Todd, Matthew H. and Kollár, László (2013) Synthesis of elongated cavitands via click reactions and their use as chemosensors. Tetrahedron, 69. pp. 8186-8190. ISSN 0040-4020

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Abstract

A very efficient modular reaction protocol was developed to attach various functionalities to a rigid cavitand scaffold. In this way, aryl, iodoaryl, benzyl, pyrrolidylmethyl groups, as well as a polyethyleneglycol chain were attached to the 'triazol-level' of the cavitand. The palladium-catalyzed ethynylation of the iodoarene moieties, followed by the copper(I)-catalyzed azide-alkyne cycloaddition produced novel cavitands with significantly elongated binding pockets. The dimensions of these molecules are calculated to be at least 9 angstrom x 18 angstrom, which place them amongst the largest unimolecular hosts obtained by pure covalent synthesis. A cavitand-based click conjugate is used for selective complexation of Cu2+ and Fe3+, providing significant fluorescent quenching.

Item Type: Article
Subjects: Q Science / természettudomány > QD Chemistry / kémia
Depositing User: Pap Viktória
Date Deposited: 06 Feb 2014 15:27
Last Modified: 06 Feb 2014 18:48
URI: http://real.mtak.hu/id/eprint/10021

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