Synthesis of phototrappable shape-shifting molecules for adaptive guest binding

AR Lippert, A Naganawa, VL Keleshian…

Index: Lippert, Alexander R.; Naganawa, Atsushi; Keleshian, Vasken L.; Bode, Jeffrey W. Journal of the American Chemical Society, 2010 , vol. 132, # 44 p. 15790 - 15799

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Citation Number: 16

Abstract

We have designed and synthesized oligosubstituted bullvalenes 1 and 2 as adaptive molecules that can change their shapes in order to bind tightly to a suitable guest. By incorporation of a photolabile o-nitroveratryloxycarbonate (NVOC) group into bullvalenes 1 and 2, tightly binding species can be selectively isolated from a population of hundreds of interconverting structural isomers. Spontaneous strain-assisted Cope rearrangements ...