Controlling Electronic Events Through Rational Structural Design in Subphthalocyanine-Corrole Dyads: Synthesis, Characterization, and Photophysical Properties

Abstract

Porphyrinoids are considered perfect candidates for their incorporation into electron donor-acceptor (D-A) arrays due to their remarkable optoelectronic properties and low reorganization energies. For the first time, a series of subphthalocyanine (SubPc) and corrole (Cor) were covalently connected through a short-range linkage. SubPc axial substitution strategies were employed, which allowed the synthesis of the target molecules in decent yields. In this context, a qualitative synthetic approach was performed to reverse the expected direction of the different electronic events. Consequently, in-depth absorption, fluorescence, and electrochemical assays enabled the study of electronic and photophysical properties. Charge separation was observed in cases of electron-donating Cors, whereas a quantitative energy transfer from the Cor to the SubPc was detected in the case of electron accepting Cors.

Keywords: corroles; electron transfer; organic photovoltaics; porphyrinoids; subphthalocyanines.