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Two‐ and Three‐Tiered Stacked Architectures by Covalent Assembly
Author(s) -
Ren Fengfeng,
Day Kody J.,
Hartley C. Scott
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201603037
Subject(s) - covalent bond , stack (abstract data type) , racemization , imine , nanotechnology , materials science , self assembly , chemistry , crystallography , computer science , stereochemistry , organic chemistry , catalysis , programming language
Simple discotic cores functionalized with reactive arms have been assembled into two‐ and three‐tiered covalent stacks through imine formation. The targets are obtained in good yields, but competing formation of misassembled byproducts highlights some of the challenges inherent to the thermodynamically controlled assembly of rigid, compact, three‐dimensional architectures. The structures comprise a central stack of arenes surrounded by a triple helix of interconnected arms. The racemization rate is strongly dependent on the number of tiers, suggesting cooperative conformational coupling in these multi‐tiered structures.