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Cyclodextrin Complexation of the Stilbene 4-(2-(4-Tert-butylphenyl)ethen-1-yl)- benzoate and the Self-assembly of Molecular Devices
Authors:Julia S Lock  Bruce L May  Philip Clements  Stephen F Lincoln  Christopher J Easton
Institution:(1) Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia;(2) Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia
Abstract:E-4-(2-(4- tert - butylphenyl) ethen-1- yl)benzoate, E-1, photoisomerizes to the Z-1 isomer and vice versa in the free state and in the binary complexes 2·E-1, 2·Z-1, 3·E-1 and 3·Z-1 where 2 is the urea-linked cyclodextrin N-(6 A -deoxy-agr-cyclodextrin-6 A - yl)-Nprime-(6 A -deoxy-beta-cyclodextrin-6 A - yl)urea and 3 is N,N- bis(6 A -deoxy-beta-cyclodextrin-6 A - yl)urea. In 2·E-1and 3·E-1 the stilbene occupies both cyclodextrin (CD) components of 2 and 3, whereas in 2·Z-1 and 3·Z-1 it only occupies one CD component while the other CD component is unoccupied. 4- tert - Butylphenolate, 4, and its carboxylate, 5, and sulfonate, 6, analogues form the ternary complex 2·Z-1·4 and its analogues and also 3·Z-1·4 and its analogues. These photoisomerize to 2·E-1and 3·E-1 and either free 4, 57 or 6 and thereby function as molecular devices.
Keywords:s>complexation  cyclodextrin  molecular device  photoisomerization
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