Unexpected but convenient synthesis of soluble meso-tetrakis(3,4-benzoquinone)-substituted porphyrins-Reference-Cited by-同舟云学术

Unexpected but convenient synthesis of soluble meso-tetrakis(3,4-benzoquinone)-substituted porphyrins

Published:2014-03 Issue:03 Volume:18 Page:173-181
ISSN:1088-4246
Container-title:Journal of Porphyrins and Phthalocyanines
language:en
Short-container-title:J. Porphyrins Phthalocyanines

Author:

Hill Jonathan P.¹²,Van Rossom Wim¹,Ishihara Shinsuke¹³,Subbaiyan Navaneetha⁴,D'Souza Francis⁴,Xie Yongshu⁵,Sanchez-Ballester Noelia M.¹,Ariga Katsuhiko¹²

Affiliation:

1. International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), Namiki 1-1, Tsukuba, Ibaraki 305-0044, Japan

2. Japan Science and Technology Agency (JST), Core Research for Evolutional Science and Technology (CREST), 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan

3. International Center for Young Scientists, National Institute for Materials Science (NIMS), Namiki 1-1, Tsukuba, Ibaraki 305-0044, Japan

4. Department of Chemistry, University of North Texas, 1155 Union Circle, Denton, #305070, Texas 76203-5017, USA

5. Key Laboratory for Advanced Materials and Institute for Fine Chemicals, East China University of Science and Technology, Meilong Rd. 130, Shanghai 200237, P. R. China

Abstract

A new route to 3,4-benzoquinone-substituted porphyrins is reported. In attempted nitration reactions on the copper(II) or nickel(II) complexes of 5,10,15,20-tetrakis(3,5-di-t-butyl-4-hydroxyphenyl)porphyrin using lithium nitrate in acetic anhydride-acetic acid/chloroform no nitration products could be detected with the main products being the corresponding complexes of 5,10,15,20-tetrakis(3,4-dioxo-5-t-butylcyclohexa-1,5-dienyl)porphyrin. These o-quinone-substituted porphyrins are available in reasonable yield (> 50%), their synthesis is simple and they are of good solubility. The electrochemical and spectroelectrochemical properties of representative o-quinone-substituted Cu ( II ) and Ni ( II ) porphyrin derivatives are also reported.

Publisher

World Scientific Pub Co Pte Lt

Subject

General Chemistry

Link

https://www.worldscientific.com/doi/pdf/10.1142/S1088424613501071

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