Synthesis of new acenaphtho[1,2-c]thiophene-based low bandgap polymers for organic photovoltaics

Donor-acceptor conjugated polymers, PDTTPDA and PDTTPDT, composed of new acenaphtho[1,2-c]thiophene or thiophene as electron donors and 1,3-dithien-2-yl-thieno[3,4-c]pyrrole-4,6-dione (DTTPD) as the electron acceptor were synthesized by a Stille cross-coupling reaction. These polymers combine interesting properties such as good solubility and excellent thermal stability. The weight-averaged molecular weights (Mw) of PDTTPDA and PDTTPDT were found to be 71,000 and 79,000 with polydispersity indices of 1.65 and 1.66, respectively. Photophysical studies revealed a low bandgap of 1.77 eV for PDTTPDA and 1.72 eV for PDTTPDT. The present study indicates that the combination of DTTPD and acenaphtho[1,2-c]thiophene building blocks can be a very effective way to lower the HOMO energy level and ultimately to enhance the Voc of polymer solar cells. The Voc reported here (up to 0.94 V) is one of the highest observed in polymer:PCBM bulk heterojunction devices, and a power conversion efficiency (PCE) of up to 3.28% was observed in the PDTTPDA devices.