Preparation and electrochemical and optical properties of unsymmetrically substituted phthalocyanines with one or two trithiole rings and related symmetric derivatives

Takeshi Kimura, Nagisa Kanota, Kenji Matsui, Ichiro Tanaka, Takaaki Tsuboi, Yutaka Takaguchi, Akinori Yomogita, Takatsugu Wakahara, Shunsuke Kuwahara, Fumi Nagatsugi, Takeshi Akasaka

研究成果: Article査読

39 被引用数 (Scopus)

抄録

4,5-Bis(benzylthio)-3,6-diethylphthalonitrile (1) was mixed with 4-t-butylphthalonitrile and then treated with lithium alkoxide in n-hexanol to produce the corresponding unsymmetrically substituted phthalocyanines (2) and (3) with two or four benzylthio groups, respectively. Treatment of phthalocyanine (2) with nickel(II) acetate yielded the corresponding metal complex 2-Ni. Two benzyl groups of 2 and 2-Ni were removed with lithium/THF/ammonia at -78°C under argon, and the dithiolate anions generated were then reacted with elemental sulfur to give monotrithiolophthalocyanines (5) and (5-Ni). A similar treatment of 3 produced bistrithiolophthalocyanine (6). Tetrakistrithiolophthalocyanine (7-Ni) was prepared by complexation of phthalocyanine (4) with nickel(II) acetate, followed by a Birch reduction of the resulting nickel(II) complex (4-Ni), and then sulfurization and cyclization of the octathiolate anions that were generated. The structures of the phthalocyanines were determined by 1H NMR and matrix-assisted laser desorption ionization time-of-flight mass spectrometry. The optical and electrochemical properties of the phthalocyanines were examined by UV-vis absorption spectroscopy and cyclic voltammetry. Treatment of 5, 5-Ni, 6, 7, and 7-Ni with trifluoroacetic acid in chloroform generated positively charged species, which were characterized by UV-vis and/or NMR spectroscopy.

本文言語English
ページ(範囲)3577-3583
ページ数7
ジャーナルInorganic chemistry
47
9
DOI
出版ステータスPublished - 2008 5月 5

ASJC Scopus subject areas

  • 物理化学および理論化学
  • 無機化学

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