Conversion of Imine to Oxazole and Thiazole Linkages in Covalent Organic Frameworks.

Autor: Waller PJ; Department of Chemistry , University of California-Berkeley , Berkeley , California 94720 , United States.; Kavli Energy NanoSciences Institute at Berkeley, and Berkeley Global Science Institute , Berkeley , California 94720 , United States.; Materials Sciences Division , Lawrence Berkeley National Laboratory , Berkeley , California 94720 , United States., AlFaraj YS; Department of Chemistry , University of California-Berkeley , Berkeley , California 94720 , United States.; Kavli Energy NanoSciences Institute at Berkeley, and Berkeley Global Science Institute , Berkeley , California 94720 , United States., Diercks CS; Department of Chemistry , University of California-Berkeley , Berkeley , California 94720 , United States.; Kavli Energy NanoSciences Institute at Berkeley, and Berkeley Global Science Institute , Berkeley , California 94720 , United States.; Materials Sciences Division , Lawrence Berkeley National Laboratory , Berkeley , California 94720 , United States., Jarenwattananon NN; Department of Chemistry , University of California-Berkeley , Berkeley , California 94720 , United States., Yaghi OM; Department of Chemistry , University of California-Berkeley , Berkeley , California 94720 , United States.; Kavli Energy NanoSciences Institute at Berkeley, and Berkeley Global Science Institute , Berkeley , California 94720 , United States.; Materials Sciences Division , Lawrence Berkeley National Laboratory , Berkeley , California 94720 , United States.; King Abdulaziz City for Science and Technology , Riyadh 11442 , Saudi Arabia.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2018 Jul 25; Vol. 140 (29), pp. 9099-9103. Date of Electronic Publication: 2018 Jul 12.
DOI: 10.1021/jacs.8b05830
Abstrakt: 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.
Databáze: MEDLINE