9,9'-Bifluorenylidene-Core Perylene Diimide Acceptors for As-Cast Non-Fullerene Organic Solar Cells: The Isomeric Effect on Optoelectronic Properties

Chemistry. 2018 Mar 15;24(16):4149-4156. doi: 10.1002/chem.201705480. Epub 2018 Feb 19.

Abstract

Two different non-fullerene small-molecule acceptors, m-PIB and p-PIB, based on 9,9'-bifluorenylidene (BF) and perylene diimide (PDI) were designed and synthesized. Four β-substituted PDIs were linked to BF in different positions. Based on DFT analysis, derivative p-PIB exhibited reduced intramolecular twisting between the PDI moieties, more delocalized wave function, and sufficiently wider π-electron delocalization than that of m-PIB. The absorption ability of p-PIB was enhanced due to increased intermolecular interactions. By blending p-PIB with poly{4,8-bis[5-(2ethylhexyl)thiophen-2-yl]benzo[1,2-b:4,5-b']dithiophene-co-3-fluorothieno[3,4-b]-thiophene-2-carboxylate} (PTB7-Th), organic solar cells (OSCs) based on p-PIB obtained a maximum power conversion efficiency of 5.95 % without any treatments. Due to the improved and balanced hole and electron mobilities, the short-circuit current and fill factor of OSCs based on PTB7-Th and p-PIB were significantly increased. The AFM and TEM results revealed that the PTB7-Th:p-PIB film had favorable nanoscale phase separation and formed a bicontinuous interpenetrating network.

Keywords: donor-acceptor systems; organic solar cells; perylene diimides; photochemistry; steric hindrance.