Naphthodifuran-based zigzag-type polycyclic arene with conjugated side chains for efficient photovoltaics.

Ladder-type conjugated structures with rigid and coplanar molecular frameworks feature longer effective conjugation, affirmative optoelectronic properties and strong intermolecular π-π interactions, which are ideal characteristics for organic photovoltaics. Here, a new "zigzag" angular-fused naphthodifuran (zNDF) based on alkoxyphenyl side chains was designed and synthesized. The distannylated zNDF building block was copolymerized with 4,7-di(5-bromothiophen-2-yl)-5,6-dioctyloxybenzo[c][1,2,5]thiadiazole and 5,8-bis(5-bromothiophen-2-yl)-2,3-bis(4-(2-ethylhexyloxy)-3-fluorophenyl)-6,7-difloroquinoxaline (Br-BT and Br-ffQx) acceptor units by Stille cross coupling reaction to form two new medium bandgap donor-acceptor polymers PzNDFP-BT and PzNDFP-ffQx, respectively. The photovoltaic properties of the copolymers blended with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as an electron acceptor were investigated. A 6.9% efficiency was achieved from the single device based on the PzNDFP-BT : PC71BM (1 : 1.5, w/w) blend film with a 0.25% 1,8-diiodooctane (DIO) additive, which is among the highest efficiency for zNDF-based polymer solar cells.