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

Chavez, Anton D.; Evans, Austin M.; Flanders, Nathan C.; Bisbey, Ryan P.; Vitaku, Edon; Chen, Lin X.; Dichtel, William R.

doi:10.1002/chem.201800459

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

Journal Article · Mon Feb 26 00:00:00 UTC 2018 · Chemistry - A European Journal

DOI:https://doi.org/10.1002/chem.201800459· OSTI ID:1422635

Chavez, Anton D. ^[1]; Evans, Austin M. ^[2]; Flanders, Nathan C. ^[2]; ^[1]; ^[2]; Chen, Lin X. ^[3]; ^[2]

Department of Chemistry Northwestern University Evanston Illinois 60208 USA, Department of Chemistry and Chemical Biology Cornell University Ithaca New York 14853 USA
Department of Chemistry Northwestern University Evanston Illinois 60208 USA
Department of Chemistry Northwestern University Evanston Illinois 60208 USA, Chemical Sciences and Engineering Division Argonne National Laboratory Argonne Illinois 60439 USA

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.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1422635

Alternate ID(s):: OSTI ID: 1481752

Journal Information:: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Journal Issue: 16 Vol. 24; ISSN 0947-6539

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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