Conducting 1D nanostructures from light-stimulated copper-metalated porphyrin–dibenzothiophene

Abstract

Control over the dimensionality of stimulated organic semiconductors has aroused significant interest in organic electronics; however, the design of such materials still remains to be decided. Herein, we have developed three dibenzothiophene-appended freebase, zinc-metalated and copper-metalated porphyrin derivatives (P_Fb-DBT, P_Zn-DBT and P_Cu-DBT) in which P_Cu-DBT leads to an anion-binding complex in chloroform upon the application of light, resulting in self-assembled 1D nanostructures with high electrical conductivity. Nevertheless, light-stimulated freebase and zinc-metalated P-DBT undergo protonation and demetalation. Electron microscopic images displayed the anion-binding-assisted 1D nanostructure using weak non-covalent interactions, which promotes enhancement in electrical conductivity among other things, as confirmed by electrochemical impedance spectra. Thus, the generation of well-defined nanostructures with improved electronic characteristics from stimuli-responsive organic dyes suggests the importance of developing various smart materials for efficient field effect transistors and sensors.