Optoelectronic and self-assembly properties of porphyrin derivatives with click chemistry modification

Abstract

A series of functionalized porphyrin molecules containing electron-rich alkynes, synthesized by means of the Sonogashira coupling reaction were further modified by reacting the ethynyl groups with click reagent through a formal [2+2] click reaction. The photophysical and electrochemical properties of the porphyrin derivatives were studied by UV/Vis spectroscopy and cyclic voltammetry. We show that the optoelectronic properties are affected by the click reagent groups and central metal ions. The functionalized porphyrin molecules show strong charge-transfer (CT) bands in the visible region (near-IR region) and potent redox activities. Through a phase-exchange self-assembly method, the highly organized morphologies were observed by scanning electron microscopy (SEM). The functionalized porphyrin molecules represent an interesting set of candidates for optoelectronic device components. The effect of the metal ions or click reagent groups on the self-assembly properties were also studied by the UV/Vis spectroscopic titration experiments.

Keywords: Sonogashira coupling; click chemistry; cyclic voltammetry; porphyrins; self-assembly.