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 - Jul 2011

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Electrochemical properties
Optical properties
Nuclear magnetic resonance
Orbital calculations
Molecular orbitals
Chloroform
Lithium
Cyclic voltammetry
Absorption spectra
Spectroscopy
phthalocyanine
1-hexanol

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Preparation and electrochemical and optical properties of α-octaalkylphthalocyanines with four fused TTF units. / Kimura, Takeshi; Namauo, Toshiharu; Amano, Kaori; Takahashi, Nobuhiro; Takaguchi, Yutaka; Hoshi, Tomonori; Kobayashi, Nagao.

In: Journal of Porphyrins and Phthalocyanines, Vol. 15, No. 7-8, 07.2011, p. 547-554.

Research output: Contribution to journalArticle

Kimura, Takeshi ; Namauo, Toshiharu ; Amano, Kaori ; Takahashi, Nobuhiro ; Takaguchi, Yutaka ; Hoshi, Tomonori ; Kobayashi, Nagao. / Preparation and electrochemical and optical properties of α-octaalkylphthalocyanines with four fused TTF units. In: Journal of Porphyrins and Phthalocyanines. 2011 ; Vol. 15, No. 7-8. pp. 547-554.
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