“Pinwheel-like” phthalocyanines with four non-peripheral chiral menthol units:Synthesis,spectroscopy, and electrochemistry

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英文篇名：“Pinwheel-like” phthalocyanines with four non-peripheral chiral menthol units:Synthesis,spectroscopy, and electrochemistry 作者：Wei ; Lv ; Junling ; Duan ; Shiyun ; Ai 英文作者：Wei Lv;Junling Duan;Shiyun Ai;College of Chemistry and Material Science, Shandong Agricultural University; 英文关键词：Phthalocyanine;;Chirality;;Synthesis;;Pinwheel-like;;Electrochemistry 中文刊名：FXKB 英文刊名：中国化学快报(英文版) 机构：College of Chemistry and Material Science, Shandong Agricultural University; 出版日期：2019-02-15 出版单位：Chinese Chemical Letters 年：2019 期：v.30 基金：supported by the National Natural Science Foundation of China(Nos. 41771342 and 21607096);; Funds of Shandong “Double Tops” Program(No. SYL2017XTTD15) 语种：英文; 页：FXKB201902025 页数：3 CN：02 ISSN：11-2710/O6 分类号：139-141

摘要

A pair of "pinwheel-like" metal free phthalocyanines, (D)-and (L)-1,8,15,22-tetrakis (2-isopropyl-5-methylcyclohexoxyl)phthalocyanine (1) were isolated for the first time from cyclic tetramerization of (D)-and (L)-3- (2-isopropyl-5-methylcyclohexoxyl)-1,2-dicyanobenzene (2), respectively, in refluxing npentanol in the presence of lithium pentanoate followed by treatment with acetic acid. Owing to the steric hindrance of the bulky menthol groups, C4 tetra-a-substituted phthalocyanine 1 is the main phthalocyanine product generated and then could be purified readily by column chromatography. The newly prepared phthalocyanine has been characterized by a series of spectroscopic technique including MALDI-TOF mass, NMR, electronic absorption and IR spectroscopy in addition to elemental analysis. In addition, their electrochemical properties have also been studied by cyclic voltammetry measurement.
        A pair of "pinwheel-like" metal free phthalocyanines, (D)-and (L)-1,8,15,22-tetrakis (2-isopropyl-5-methylcyclohexoxyl)phthalocyanine (1) were isolated for the first time from cyclic tetramerization of (D)-and (L)-3- (2-isopropyl-5-methylcyclohexoxyl)-1,2-dicyanobenzene (2), respectively, in refluxing npentanol in the presence of lithium pentanoate followed by treatment with acetic acid. Owing to the steric hindrance of the bulky menthol groups, C4 tetra-a-substituted phthalocyanine 1 is the main phthalocyanine product generated and then could be purified readily by column chromatography. The newly prepared phthalocyanine has been characterized by a series of spectroscopic technique including MALDI-TOF mass, NMR, electronic absorption and IR spectroscopy in addition to elemental analysis. In addition, their electrochemical properties have also been studied by cyclic voltammetry measurement.

引文

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