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Regulating Molecular Recognition with C‐Shaped Strips Attained by Chirality‐Assisted Synthesis
Author(s) -
Liu Xiaoxi,
Weinert Zackariah J.,
Sharafi Mona,
Liao Chenyi,
Li Jianing,
Schneebeli Severin T.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201506793
Subject(s) - pillar , supramolecular chemistry , chirality (physics) , strips , molecular recognition , molecule , stereochemistry , chemistry , supramolecular chirality , nanotechnology , materials science , crystallography , physics , organic chemistry , chiral symmetry breaking , structural engineering , quantum mechanics , nambu–jona lasinio model , engineering , composite material , quark
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.