Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 16, Pages 3989-3993Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201800459
Keywords
covalent organic frameworks; dynamic covalent chemistry; imines; self-assembly; supramolecular chemistry
Categories
Funding
- Army Research Office through the Multidisciplinary University Research Initiative (MURI) [W911NF-15-1-0447]
- National Defense Science and Engineering Graduate Fellowship (NDSEG)
- National Science Foundation (NSF) [CHE-1048773]
- Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource [NSF NNCI-1542205]
- State of Illinois
- International Institute for Nanotechnology (IIN)
- DOE Office of Science by Argonne National Laboratory [DE-AC02-06CH11357]
- Basic Energy Science, CBG Division, US Department of Energy
- National Science Foundation [0960140]
- National Science Foundation Graduate Research Fellowship [DGE-1324585]
- DGE-1324585
- International Institute for Nanotechnology
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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.
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