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

Text TETRAHEDRON2013_cavitand.pdf Restricted to Repository staff only Download (985kB) | Request a copy

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.

Actions (login required)

Edit Item