Substitution Effect of 1,7-Asymmetrically Substituted 3,4:9,10-Perylenebis(dicarboximide) Dyes

Abstract

1,7-Asymmetrically substituted 3,4:9,10-perylenebis(dicarboximide) dyes (2a, 2b, and 3) with electron donor or acceptor groups have been synthesized in good yields under mild conditions. The electrochemistry and steady-state spectroscopy of these perylene bisimides were discussed. The strong electron donating pyrrolidinyl and electron withdrawing bromine substitutes led to a serious deviation from intrinsic electronic structure of the perylene bisimide core. Furthermore, the packing behaviors in solution were investigated with absorption spectra. These results were in good agreement with the theory calculations at B3LYP/6-31G* level and made them a valuable addition to the family of robust perylene-based chromophores that can be used to develop new photoactive charge transport materials.