期刊
TETRAHEDRON
卷 69, 期 38, 页码 8186-8190出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.07.044
关键词
Cavitand; Azide-alkyne cycloaddition; Copper; Iron; Palladium
资金
- Hungarian Academy of Sciences
- [SROP-4.2.2.A-11/1/KONV-2012-0065]
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. (C) 2013 Published by Elsevier Ltd.
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