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 · 26 February 2018 · Chemistry - A European Journal

DOI:https://doi.org/10.1002/chem.201800459· OSTI ID:1481752

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

Macrocyclesbased on directional bonding and dynamic covalentbond exchange can be design ed with specificpore shapes, sizes, andfunctionality.These sys- tems retain many of the design criteria and desirableas- pects of two-dimensional (2D) covalent organic frame- works (COFs)but are more easily processed. Here we access discrete hexagonal imine-linked macrocycles by condensing atruncated analogueof1,3,5-tris(4-aminophe- nyl)benzene(TAPB) with terephthaldehyde (PDA). The monomers first condense into polymers buteventually convertinto hexagonal macrocycles in high yield. The high selectivity for hexagonal macrocycles is enforcedby their aggregation and crystallization into layered struc- tures with more sluggish imine exchange. Their formation and exchange processes provide new insight into how imine-linked 2D COF simultaneously polymerize and crys- tallize. Solutions of theseassembled macrocycles were cast into oriented, crystalline films, expanding the poten- tial routes to 2D materials.

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

DOE Contract Number:: AC02-06CH11357

OSTI ID:: 1481752

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

Publisher:: ChemPubSoc Europe

Country of Publication:: United States

Language:: English

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