Regioisomer‐Free C4h β‐Tetrakis(tert‐butyl)metallo‐phthalocyanines: Regioselective Synthesis and Spectral Investigations

ChemistryOpen

Norihito Iida³  Kenta Tanaka³  Etsuko Tokunaga²  Hiromi Takahashi¹ 

[1] System Instruments Co., Ltd, Tokyo, Japan;Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, (Japan;Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, Japan

关键词: aggregation;    phthalocyanines;    protecting groups;    regioselectivity;    silicon;    synthesis;   

DOI  :  10.1002/open.201402093

来源: Wiley

【 摘 要 】

Abstract

Metal β-tetrakis(tert-butyl)phthalocyanines are the most commonly used phthalocyanines due to their high solubility, stability, and accessibility. They are commonly used as a mixture of four regioisomers, which arise due to the tert-butyl substituent on the β-position, and to the best of our knowledge, their regioselective synthesis has yet to be reported. Herein, the C_4h-selective synthesis of β-tetrakis(tert-butyl)metallophthalocyanines is disclosed. Using tetramerization of α-trialkylsilyl phthalonitriles with metal salts following acid-mediated desilylation, the desired metallophthalocyanines were obtained in good yields. Upon investigation of regioisomer-free zinc β-tetrakis(tert-butyl)phthalocyanine using spectroscopy, the C_4h single isomer described here was found to be distinct in the solid state to zinc β-tetrakis(tert-butyl)phthalocyanine obtained by a conventional method.

【 授权许可】

CC BY-NC-ND   
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

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