Equilibration of Imine‐Linked Polymers to Hexagonal Macrocycles Driven by Self‐Assembly

Equilibration of Imine‐Linked Polymers to Hexagonal Macrocycles Driven by Self‐Assembly Macrocycles based on directional bonding and dynamic covalent bond exchange can be designed with specific pore shapes, sizes, and functionality. These systems retain many of the design criteria and desirable aspects of two‐dimensional (2D) covalent organic frameworks (COFs) but are more easily processed. Here we access discrete hexagonal imine‐linked macrocycles by condensing a truncated analogue of 1,3,5‐tris(4‐aminophenyl)benzene (TAPB) with terephthaldehyde (PDA). The monomers first condense into polymers but eventually convert into hexagonal macrocycles in high yield. The high selectivity for hexagonal macrocycles is enforced by their aggregation and crystallization into layered structures with more sluggish imine exchange. Their formation and exchange processes provide new insight into how imine‐linked 2D COF simultaneously polymerize and crystallize. Solutions of these assembled macrocycles were cast into oriented, crystalline films, expanding the potential routes to 2D materials. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry - A European Journal Wiley

Equilibration of Imine‐Linked Polymers to Hexagonal Macrocycles Driven by Self‐Assembly

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Publisher
Wiley
Copyright
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
0947-6539
eISSN
1521-3765
D.O.I.
10.1002/chem.201800459
Publisher site
See Article on Publisher Site

Abstract

Macrocycles based on directional bonding and dynamic covalent bond exchange can be designed with specific pore shapes, sizes, and functionality. These systems retain many of the design criteria and desirable aspects of two‐dimensional (2D) covalent organic frameworks (COFs) but are more easily processed. Here we access discrete hexagonal imine‐linked macrocycles by condensing a truncated analogue of 1,3,5‐tris(4‐aminophenyl)benzene (TAPB) with terephthaldehyde (PDA). The monomers first condense into polymers but eventually convert into hexagonal macrocycles in high yield. The high selectivity for hexagonal macrocycles is enforced by their aggregation and crystallization into layered structures with more sluggish imine exchange. Their formation and exchange processes provide new insight into how imine‐linked 2D COF simultaneously polymerize and crystallize. Solutions of these assembled macrocycles were cast into oriented, crystalline films, expanding the potential routes to 2D materials.

Journal

Chemistry - A European JournalWiley

Published: Jan 15, 2018

Keywords: ; ; ; ;

References

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