Perylenebisimide regioisomers: Effect of substituent position on their spectroscopic, electrochemical, and photovoltaic properties

•The single-crystal structure of a 1,6-disubstituted perylenebisimide is elucidated here for the first time.•Perylenebisimide regioisomers on solar cell performance are examined.•Power conversion efficiency of the 1,7-perylenebisimide based is higher than those of 1,6-perylenebisimide based device.

New disubstituent fluorinated perylenebisimide regioisomers were synthesized and characterized. The single-crystal structure of a 1,6-disubstituted perylenebisimide was elucidated for the first time, which revealed that the molecules are arranged in stacks along the b-axis of the unit cell and share more than 50% of their core surface. Owing to the steric encumbrance of the substituents, the perylene cores were highly twisted. The effect of substituent positions on their spectroscopic, electrochemical, and photovoltaic properties were also examined. Moreover, the two substituent positions on perylenebisimides were found to have a large impact on the solar cell performance. Different perylenebisimide regioisomers made an impact on open circuit voltage, but strongly affected the short circuit current density, indirectly influencing the overall photovoltaic performance of the device.

Graphical abstractThe effect of substituent positions on perylenebisimide regioisomers (PBIs) have a large impact on the short circuit current density so the overall performance of the device in the solar cell performance.Figure optionsDownload full-size imageDownload as PowerPoint slide