Facile, Mild-Temperature Synthesis of Metal-Free Phthalocyanines

Fangdi Cong; Hongzhen Jiang; Xiguang Du; Wei Yang; Shulin Zhang

doi:10.1055/a-1499-8865

Synthesis, Table of Contents

Synthesis 2021; 53(15): 2656-2664
DOI: 10.1055/a-1499-8865

paper

Facile, Mild-Temperature Synthesis of Metal-Free Phthalocyanines

Fangdi Cong‡

^aFaculty of Chemistry, Northeast Normal University, Renmin Street No. 5268, Changchun 130024, P. R. of China

^bTianjin Key Laboratory of Aqua-ecology and Aquaculture, College of Basic Science, Tianjin Agricultural University, Jinjing Road No. 22, Tianjin 300392, P. R. of China

,

Hongzhen Jiang‡

^bTianjin Key Laboratory of Aqua-ecology and Aquaculture, College of Basic Science, Tianjin Agricultural University, Jinjing Road No. 22, Tianjin 300392, P. R. of China

,

Xiguang Du∗

^aFaculty of Chemistry, Northeast Normal University, Renmin Street No. 5268, Changchun 130024, P. R. of China

,

Wei Yang

^bTianjin Key Laboratory of Aqua-ecology and Aquaculture, College of Basic Science, Tianjin Agricultural University, Jinjing Road No. 22, Tianjin 300392, P. R. of China

,

Shulin Zhang∗

^bTianjin Key Laboratory of Aqua-ecology and Aquaculture, College of Basic Science, Tianjin Agricultural University, Jinjing Road No. 22, Tianjin 300392, P. R. of China

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Abstract

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Abstract

It is important for the synthesis and research of phthalocyanine compounds for these compounds to be easily obtained at low temperature. We observed that metal-free phthalocyanine was sometimes found in a simple system used to synthesize phthalocyanine precursors at room temperature, and further studies showed that the key to the effective formation of phthalocyanines at low temperature lay in the presence of equal volumes of alcohol and amine, in addition to substrate phthalonitriles and solvents, in the reaction system. A synthetic mechanism was proposed and facile syntheses have been realized, such as the synthesis of tetra-α(β)-nitrophthalocyanines and tetra-α(β)-(4-tert-butylphenoxy)phthalocyanines from the corresponding substituted phthalonitriles at mild temperature (37 °C). The results are significant for the design and synthesis of new phthalocyanine derivatives, and the method is convenient and easy to adopt for general use in standard laboratories.

Key words

metal-free phthalocyanine - facile synthesis - characterization - room temperature - amine - alcohol - phthalonitrile

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References

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