Preparation and electrochemical and optical properties of α-octaalkylphthalocyanines with four fused TTF units

Takeshi Kimura, Toshiharu Namauo, Kaori Amano, Nobuhiro Takahashi, Yutaka Takaguchi, Tomonori Hoshi, Nagao Kobayashi

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

3,6-Dialkylphthalonitriles (6a) and (6b) with a fused TTF unit at 4,5-positions were prepared from dialkyltetrabromobenzenes via five step reactions (alkyl: butyl and octyl). Compounds 6a and 6b were treated with lithium in n-hexanol at 120 °C for 3 h to produce α- octaalkyltetrakis(tetrathiafulvaleno)phthalocyanines (8a) and (8b), respectively. The structure of the products was determined by 1H NMR, FAB MS, and MALDI TOF MS. The 1H NMR measurement was performed in chloroform-d at around 55 °C because of their higher aggregative property. Electrochemical and optical properties of 8a and 8b were examined by cyclic voltammetry and UV-vis and MCD spectroscopy. Molecular orbital calculations succeeded in reproducing the observed absorption spectrum of tetrakis(tetrathiafulvaleno)phthalocyanine.

Original languageEnglish
Pages (from-to)547-554
Number of pages8
JournalJournal of Porphyrins and Phthalocyanines
Volume15
Issue number7-8
DOIs
Publication statusPublished - 2011 Jan 1

Keywords

  • MCD spectrum
  • UV-vis spectrum
  • benzotrithiole
  • electrochemistry
  • phthalocyanine
  • tetrathiafulvalene

ASJC Scopus subject areas

  • Chemistry(all)

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