2,3,9,10,16,17,23,24-Octakis(hexylsulfonyl)phthalocyanines with good n-type semiconducting properties. Synthesis, spectroscopic, and electrochemical characteristics
作者： Yi Zhang , Pan Ma , Peihua Zhu , Xianyao Zhang , Yingning Gao
DOI: 10.1039/C1JM10295H
关键词: Molecule 、 Cyclic voltammetry 、 Phthalocyanine 、 Phthalonitrile 、 Differential pulse voltammetry 、 Chemistry 、 Electrochemistry 、 Density functional theory 、 Inorganic chemistry 、 Physical chemistry 、 Saturated calomel electrode
摘要: The synthesis of peripherally octa-substituted phthalocyanine compounds with eight strong electron-withdrawing hexylsulfonyl groups was systematically studied. Three new phthalocyanines M[Pc(SO2C6H13)8] [Pc(SO2C6H13)8 = 2,3,9,10,16,17,23,24-octakis(hexylsulfonyl)phthalocyaninate; M 2H (1), Cu (2), Zn (3)] were synthesized via direct cyclic tetramerization 4,5-di(hexylsulfonyl)phthalonitrile or through a diiminoisoindoline intermediate. Compounds 1–3 could alternatively be prepared by oxidation the hexylthio substituents in corresponding 2,3,9,10,16,17,23,24-octakis(hexylthio)phthalocyanine M[Pc(SC6H13)8] (M 2H, Cu, Zn) m-chloroperbenzoic acid. They fully characterized elemental analysis and series spectroscopic methods. Their electrochemistry studied voltammetry (CV) differential pulse (DPV). Density function theory (DFT) calculations conducted to study effect on electronic structure molecules. Particularly, first reduction potentials range −0.30∼−0.04 V vs. saturated calomel electrode (SCE) for reveal their n-type semiconducting nature. current–voltage characteristics aggregates demonstrate good properties especially 1 2 conductivity value 5.24 × 10−4 2.73 S m−1, respectively.
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