Synthesis and Properties of Norphthalocyanines Functionalized with a Tetrathiacrown Ether–Tetrathiafulvalene Substituent

Abstract

To construct novel ion receptors and D-A self-assembly systems for materials with better functions, the annulation of a tetrathiafulvalene donor with a magnesium norphthalocyanine core via a flexible tetrathiacrown ether bridge afforded a new triad 1. The structure of this product was characterized by 1H NMR and infrared spectroscopy, time-of-flight mass spectrometry, and elemental analysis. The optical and electrochemical properties were investigated using UV–vis spectroscopy and cyclic voltammetry. The complex of triad 1 and 2,3,5,6- tetrafluoro-7,7,8,8-tetracyanoquinodimethane produced electron transfer with a radical cationic character, as confirmed by UV–Vis and electron paramagnetic resonance analysis. Furthermore, the target compound presented evident intramolecular charge-transfer interactions in ground states, which were explained using density functional theory. Furthermore, norphthalocyanine 1 was able to coordinate Ag+ through the peripheral ligating oxathiaether crown.