Chemical Conversion of Linkages in Covalent Organic Frameworks

Waller, Peter J.; Lyle, Steven J.; Osborn Popp, Thomas M.; Diercks, Christian S.; Reimer, Jeffrey A.; Yaghi, Omar M.

doi:10.1021/jacs.6b08377

Chemical Conversion of Linkages in Covalent Organic Frameworks

Journal Article · Tue Nov 15 00:00:00 EST 2016 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.6b08377· OSTI ID:1464142

Waller, Peter J. ^[1]; Lyle, Steven J. ^[1]; Osborn Popp, Thomas M. ^[1]; Diercks, Christian S. ^[1]; Reimer, Jeffrey A. ^[2]; Yaghi, Omar M. ^[3]

Univ. of California, Berkeley, CA (United States). Berkeley Global Science Inst. and Kavli Energy NanoSciences Inst.; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States)
Univ. of California, Berkeley, CA (United States). Berkeley Global Science Inst. and Kavli Energy NanoSciences Inst.; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); King Fahd Univ. of Petroleum and Minerals, Dhahran (Saudi Arabia)

The imine linkages of two layered, porous covalent organic frameworks (COFs), TPB-TP-COF ([C₆H₃(C₆H₄N)₃]₂[C₆H₄(CH)₂]₃, 1) and 4PE-1P-COF ([C₂(C₆H₄N)₄][C₆H₄(CH)₂]₂, 2), have been transformed into amide linkages to make the respective isostructural amide COFs 1' and 2' by direct oxidation with retention of crystallinity and permanent porosity. Remarkably, the oxidation of both imine COFs is complete, as assessed by FT-IR and¹³C CP-MAS NMR spectroscopy and demonstrates (a) the first chemical conversion of a COF linkage and (b) how the usual “crystallization problem” encountered in COF chemistry can be bypassed to access COFs, such as these amides, that are typically thought to be difficult to obtain by the usual de novo methods. The amide COFs show improved chemical stability relative to their imine progenitors.

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Gas Separations Relevant to Clean Energy Technologies (CGS); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: BASF SE, Germany; National Science Foundation (NSF); Saudi Aramco, Saudi Arabia; US Army Research Office (ARO); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-05CH11231; SC0001015

OSTI ID:: 1464142

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 48 Vol. 138; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Covalent Organic Frameworks as a Platform for Multidimensional Polymerization Bisbey, Ryan P.; Dichtel, William R. ACS Central Science, Vol. 3, Issue 6 https://doi.org/10.1021/acscentsci.7b00127	journal	May 2017
Stable and ordered amide frameworks synthesised under reversible conditions which facilitate error checking Stewart, David; Antypov, Dmytro; Dyer, Matthew S. Nature Communications, Vol. 8, Issue 1 https://doi.org/10.1038/s41467-017-01423-5	journal	October 2017
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Chemical Conversion of Linkages in Covalent Organic Frameworks

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