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

doi:10.1142/S1088424611003288

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 journal › Article › peer-review

14 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 language	English
Pages (from-to)	547-554
Number of pages	8
Journal	Journal of Porphyrins and Phthalocyanines
Volume	15
Issue number	7-8
DOIs	https://doi.org/10.1142/S1088424611003288
Publication status	Published - 2011

Keywords

MCD spectrum
UV-vis spectrum
benzotrithiole
electrochemistry
phthalocyanine
tetrathiafulvalene

ASJC Scopus subject areas

Chemistry(all)

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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, 2011, p. 547-554.

Research output: Contribution to journal › Article › peer-review

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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.",

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AU - Kimura, Takeshi

AU - Namauo, Toshiharu

AU - Amano, Kaori

AU - Takahashi, Nobuhiro

AU - Takaguchi, Yutaka

AU - Hoshi, Tomonori

AU - Kobayashi, Nagao

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AB - 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.

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KW - UV-vis spectrum

KW - benzotrithiole

KW - electrochemistry

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KW - tetrathiafulvalene

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

Abstract

Keywords

ASJC Scopus subject areas

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