Regulating Molecular Recognition with C-Shaped Strips Attained by Chirality-Assisted Synthesis
Dr. Xiaoxi Liu
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Search for more papers by this authorZackariah J. Weinert
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Search for more papers by this authorMona Sharafi
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Search for more papers by this authorDr. Chenyi Liao
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Search for more papers by this authorCorresponding Author
Prof. Jianing Li
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)Search for more papers by this authorCorresponding Author
Prof. Severin T. Schneebeli
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)Search for more papers by this authorDr. Xiaoxi Liu
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Search for more papers by this authorZackariah J. Weinert
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Search for more papers by this authorMona Sharafi
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Search for more papers by this authorDr. Chenyi Liao
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Search for more papers by this authorCorresponding Author
Prof. Jianing Li
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)Search for more papers by this authorCorresponding Author
Prof. Severin T. Schneebeli
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)
Department of Chemistry, The University of Vermont, Burlington, VT 05405 (USA)Search for more papers by this authorAbstract
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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