Electron-deficient 1,2,7,8-tetraazaperylene derivative: Efficient synthesis and copolymerization

Development of electron-deficient organic semiconducting monomers is the key role in the construction of donor (D)-acceptor (A) conjugated polymers. In this work, a new type of 1,2,7,8-tetraazaperylene derivative 3,9-bis(5-bromo-4-hexylthienyl)-1,2,7,8-tetraazaperylene (Br-TPAL) with two terminal bromine groups, has been efficiently synthesized. Upon transition-metal catalyzed cross-coupling, Br-TPAL was facile to copolymerize with various monomers, to form three donor–acceptor conjugated polymers PTPAL-OBDT, PTPAL-TBDT PTPAL-DPP in high yields. The electronic structures of the resulting polymers enable being finely tuned through changing the building blocks. They exhibited very rich optoelectronic properties, for example, their absorption bands covered the nearly whole visible regions, or even extending to the NIR regions. These promising characters render them highly desirable for high-performance electronic devices.