Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 29, Pages 9099-9103Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b05830
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Funding
- Army Research Office through a Multidisciplinary University Research Initiatives (MURI) [WG11NF-15-1-0047]
- NSF [1144885]
- Berkeley Center for Green Chemistry [1144885]
- Gifted Student Program Scholarship through the King Abdullah University of Science and Technology
- Kavli ENSI Philomathia Graduate Student Fellowship
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Imine-linked ILCOF-1 based on 1,4-phenylenediamine and 1,3,6,8-tetrakis(4-formylphenyl)-pyrene was converted through consecutive linker substitution and oxidative cyclization to two isostructural covalent organic frameworks (COFs), having thiazole and oxazole linkages. The completeness of the conversion was assessed by infrared and solid-state NMR spectroscopies, and the crystallinity of the COFs was confirmed by powder X-ray diffraction. Furthermore, the azole-linked COFs remain porous, as shown by nitrogen sorption experiments. The materials derived in this way demonstrate increased chemical stability, relative to the imine-linked starting material. This constitutes a facile method for accessing COFs and linkages that are otherwise difficult to crystallize due to their inherently limited microscopic reversibility.
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