Dynamic helical cyclophanes with two quadruply-bridged planes arranged in an "obverse and/or reverse" relation

Chemical Science
Ryo KatoonoTakanori Suzuki

Abstract

We describe the design of two types of cyclophanes that generate dynamic helicity through the twisting of two planes in a clockwise or counterclockwise direction to give (M)- or (P)-helicity. We used a rectangular and anisotropic plane of 1,2,4,5-tetrakis(phenylethynyl)benzene (TPEB), since it can be stacked in pairs in two ways, in parallel or orthogonally, to be identified as distinct cyclophane molecules. We adopted a synthetic strategy for obtaining these two cyclophanes as a mixture using a macrocyclic intermediate that possessed two rotatable phenyl rings. We introduced necessary parts into the rotators to give a mixture of rotational isomers leading to a parallel or orthogonal arrangement of TPEBs, and then doubly bridged two planes of TPEB to form quadruply-bridged cyclophanes. We consider that such two planes in each cyclophane are in an "obverse and/or reverse" relation. In each cyclophane, we found unique dynamic helical forms with (M)- or (P)-helicity as well as an inherently non-chiral form. Normally, the screw-sense preference of dynamic helicity would be controlled through the intramolecular or supramolecular transmission of central chirality, when a chiral auxiliary is attached to the cyclophanes or a chiral gue...Continue Reading

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Citations

Nov 14, 2018·Physical Chemistry Chemical Physics : PCCP·Peng LiuXiaoyao Tan
Feb 10, 2018·Journal of the American Chemical Society·Hiroki SatoMichael J Krische
May 16, 2018·Organic Letters·Zacharias J Kinney, C Scott Hartley
Mar 18, 2017·Journal of the American Chemical Society·Zacharias J Kinney, C Scott Hartley

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