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 | |
| Publication status | Published - Jul 2011 |
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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 journal › Article
}
TY - JOUR
T1 - Preparation and electrochemical and optical properties of α-octaalkylphthalocyanines with four fused TTF units
AU - Kimura, Takeshi
AU - Namauo, Toshiharu
AU - Amano, Kaori
AU - Takahashi, Nobuhiro
AU - Takaguchi, Yutaka
AU - Hoshi, Tomonori
AU - Kobayashi, Nagao
PY - 2011/7
Y1 - 2011/7
N2 - 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.
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.
KW - benzotrithiole
KW - electrochemistry
KW - MCD spectrum
KW - phthalocyanine
KW - tetrathiafulvalene
KW - UV-vis spectrum
UR - http://www.scopus.com/inward/record.url?scp=80053127002&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=80053127002&partnerID=8YFLogxK
U2 - 10.1142/S1088424611003288
DO - 10.1142/S1088424611003288
M3 - Article
AN - SCOPUS:80053127002
VL - 15
SP - 547
EP - 554
JO - Journal of Porphyrins and Phthalocyanines
JF - Journal of Porphyrins and Phthalocyanines
SN - 1088-4246
IS - 7-8
ER -