Synthesis of n-type semiconducting polymer consisting of benzodipyrrolidone and thieno-[3,4c]-pyrrole-4,6-dione via C H direct arylation

Abstract

Direct arylation polycondensation of 3,7-bis(4-bromophenyl)-1,5-bis(2-octyldodecyl)benzo[1,2-b:4,5-b']dipyrrole-2,6(1H,5H)-dione with 5-(2-ethylhexyl)-thieno-[3,4-c]-pyrrole-4,6-dione gave the corresponding benzodipyrrolidone-based conjugated polymer with a molecular weight of 147,000 in 92% yield. The optical and thermal properties of the polymer were evaluated. The polymer showed n-type semiconducting behavior in organic field-effect transistors with an electron mobility of 1.3 ± 0.2 x 10-3 cm 2 V-1 s-1 .

Highly Efficient and Balanced Charge Transport in Thieno[3,4-c]pyrrole-4,6-dione Copolymers: Dramatic Influence of Thieno[3,2-b]thiophene Comonomer on Alignment and Charge Transport

“…In detail, a solar cell efficiency of 9.21% in combination with a fullerene-based acceptor and an OFET hole mobility of 1.29 cm 2 V –1 s –1 was achieved, which are both the highest values for TPD copolymers reported to date. Because of the high electron withdrawing properties of the TPD unit, electron transport can also be facilitated in TPD copolymers. − However, only a few examples are reported to date using TPD copolymers as acceptor materials in all-polymer solar cells. , Ambipolar charge transport was shown for TPD copolymers carrying thiophene , and for bithienopyrroledione-based copolymers in OFET devices. In the latter, an electron mobility of 1.02 cm 2 V –1 s –1 and a hole mobility of 0.33 cm 2 V –1 s –1 were shown.…”