Synthesis and characterization of poly(arylene ether ketone)s with 3,6-diphenyl-9H-carbazole pendants using C–N coupling reaction

Abstract

3,6-Diphenyl-9 H-carbazole pendants are grafted herein to poly(arylene ether ketone)s (PAEKs) via the Ullmann C–N coupling reaction. To the best of our knowledge, this is the first time that PAEKs containing a carbazole pendant (Cz) have been synthesized through the Ullmann C–N coupling reaction. The high molecular weights of PAEK-Cz (PAEKs with 3,6-diphenyl-9 H-carbazole pendants) are inherited from their precursors, owing to the high reactivity of their monomers. The obtained PAEK-Cz- x polymers exhibit good solubility in most common organic solvents and excellent thermal stabilities, with the 5% weight loss temperatures for all products being above 598°C under a nitrogen atmosphere. The glass transition temperatures are all above 199°C and can be controlled by adjusting the feed ratio of monomers. The polymer membranes obtained by the casting method are tough and thus have strong potential for practical applications.

Diindolocarbazole‐Based Rigid Donor‐Acceptor TADF Molecules for Energy and Electron Transfer Photocatalysis**

“…Two tertiary butyl groups were incorporated in the phenyl group to minimize the possibility of self‐aggregation of these molecules in the solid state. Donor Ph‐CBZ was synthesized by bromination of carbazole followed by Suzuki coupling reaction with phenylboronic acid [40] . Finally, the TADF molecules were synthesized by Buchwald‐Hartwig coupling reaction between donors DI, Ph‐CBZ and acceptors IQ, 2FIQ using tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 as catalyst, tri‐tert‐butylphosphine tetrafluoroborate as co‐catalyst and sodium tert‐butoxide as base as shown in Scheme 1 [41] .…”

“…Donor Ph-CBZ was synthesized by bromination of carbazole followed by Suzuki coupling reaction with phenylboronic acid. [40] Finally, the TADF molecules were synthesized by Buchwald-Hartwig coupling reaction between donors DI, Ph-CBZ and acceptors IQ, 2FIQ using tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 as catalyst, tri-tert-butylphosphine tetrafluoroborate as co-catalyst and sodium tert-butoxide as base as shown in Scheme 1. [41] All compounds were purified via column chromatography and characterized using 1 H NMR, 13 C NMR and high-resolution mass spectrometry (HRMS).…”