Regulating Molecular Recognition with C-Shaped Strips Attained by Chirality-Assisted Synthesis

Angewandte Chemie
Xiaoxi LiuSeverin T Schneebeli

Abstract

Chirality-assisted synthesis (CAS) is a general approach to control the shapes of large molecular strips. CAS is based on enantiomerically pure building blocks that are designed to strictly couple in a single geometric orientation. Fully shape-persistent structures can thus be created, even in the form of linear chains. With CAS, selective recognition between large host and guest molecules can reliably be designed de novo. To demonstrate this concept, three C-shaped strips that can embrace a pillar[5]arene macrocycle were synthesized. The pillar[5]arene bound to the strips was a better host for electron-deficient guests than the free macrocycle. Experimental and computational evidence is provided for these unique cooperative interactions to illustrate how CAS could open the door towards the precise positioning of functional groups for regulated supramolecular recognition and catalysis.

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Citations

May 17, 2017·Angewandte Chemie·Mona SharafiSeverin T Schneebeli
Apr 6, 2017·Nature Communications·Kyle E MurphySeverin T Schneebeli
Jul 24, 2018·Organic & Biomolecular Chemistry·Philipp RommelmannDietmar Kuck
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Nov 8, 2018·Angewandte Chemie·Joseph P CampbellSeverin T Schneebeli
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Dec 15, 2018·The Journal of Organic Chemistry·Wai-Shing WongHak-Fun Chow
Jan 29, 2020·The Journal of Organic Chemistry·Philippe WagnerMichael Mastalerz

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