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

• Published in: Molecules (Basel, Switzerland) Vol. 28; no. 3; p. 916
• Main Authors: Hou, Ruibin, Liu, Xiaoyu, Xia, Yan, Li, Dongfeng
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 17.01.2023; MDPI
• Subjects: Charge transfer; Chemical engineering; Chemical engineering research; Chemical properties; Chemical reactions; Chemical synthesis; Density functional theory; Electrochemical analysis; Electrochemistry; Electrolytes; Electron donor-acceptor complexes; Electron paramagnetic resonance; Electron spin resonance; Electron transfer; Ethers; Infrared analysis; Infrared spectroscopy; intramolecular charge-transfer; Ligands; Macrocycles; Magnesium; Mass spectrometry; Mass spectroscopy; NMR; norphthalocyanine; Nuclear magnetic resonance; Organosulfur compounds; Oxidation; Production processes; Self-assembly; Tetracyanoquinodimethane; tetrathiacrown ether; tetrathiafulvalene; China; intramolecular charge-transfer; norphthalocyanine; tetrathiacrown ether; density functional theory; tetrathiafulvalene
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules28030916

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 . 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 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 was able to coordinate Ag through the peripheral ligating oxathiaether crown.