Show simple item record

dc.contributor.authorWaller, Peter J.
dc.contributor.authorAlFaraj, Yasmeen S.
dc.contributor.authorDiercks, Christian S.
dc.contributor.authorJarenwattananon, Nanette N.
dc.contributor.authorYaghi, Omar M.
dc.date.accessioned2022-06-06T06:39:43Z
dc.date.available2022-06-06T06:39:43Z
dc.date.issued2018-07-12
dc.identifier.citationWaller, P. J., AlFaraj, Y. S., Diercks, C. S., Jarenwattananon, N. N., & Yaghi, O. M. (2018). Conversion of Imine to Oxazole and Thiazole Linkages in Covalent Organic Frameworks. Journal of the American Chemical Society, 140(29), 9099–9103. doi:10.1021/jacs.8b05830
dc.identifier.issn0002-7863
dc.identifier.doi10.1021/jacs.8b05830
dc.identifier.urihttp://hdl.handle.net/10754/678628
dc.description.abstractImine-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.
dc.description.sponsorshipThis work was supported by the Army Research Office through a Multidisciplinary University Research Initiatives (MURI) Award through Grant WG11NF-15-1-0047. P.J.W. additionally thanks the NSF and the Berkeley Center for Green Chemistry for support via the Systems Approach to Green Energy Integrative Graduate Education and Research Traineeship (1144885). Y.S.F. is supported by the Gifted Student Program Scholarship through the King Abdullah University of Science and Technology. C.S.D. acknowledges funding through a Kavli ENSI Philomathia Graduate Student Fellowship. The authors thank Dr. Chenfei Zhao, Mary E. Garner and Robinson W. Flaig for helpful discussions.
dc.publisherAmerican Chemical Society (ACS)
dc.relation.urlhttps://pubs.acs.org/doi/10.1021/jacs.8b05830
dc.titleConversion of Imine to Oxazole and Thiazole Linkages in Covalent Organic Frameworks
dc.typeArticle
dc.identifier.journalJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
dc.identifier.wosutWOS:000440515200020
dc.contributor.institutionDepartment of Chemistry, University of California—Berkeley, Berkeley, California 94720, United States
dc.contributor.institutionKavli Energy NanoSciences Institute at Berkeley, and Berkeley Global Science Institute, Berkeley, California 94720, United States
dc.contributor.institutionMaterials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States
dc.contributor.institutionKing Abdulaziz City for Science and Technology, Riyadh 11442, Saudi Arabia
dc.identifier.volume140
dc.identifier.issue29
dc.identifier.pages9099-9103
dc.identifier.eid2-s2.0-85050697009
kaust.acknowledged.supportUnitGifted Student Program Scholarship


This item appears in the following Collection(s)

Show simple item record