Comparative study of spectroscopic properties of α- Or β-butyloxy-substituted tribenzotetraazachlorin-fullerene conjugates

Takamitsu Fukuda; Hironori Kaneko; Nagao Kobayashi

doi:10.1142/S1088424609001327

Comparative study of spectroscopic properties of α- Or β-butyloxy-substituted tribenzotetraazachlorin-fullerene conjugates

Takamitsu Fukuda, Hironori Kaneko, Nagao Kobayashi

SCI - Chemistry

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

4 Citations (Scopus)

Abstract

Mixed condensation of 1,2-dicyanofullerene (1) and 3,6- dibutyloxyphthalonitrile (2a) in the presence of nickel chloride dihydrate (NiCl₂·2H₂O) in quinoline forms an α-hexabutyloxy-substituted tribenzotetraazachlorin (TBTAC)-fullerene (C₆₀) conjugate (3). UV-vis absorption and magnetic circular dichroism (MCD) properties of 3 have been obtained, and the results compared with those of the β-substituted isomer (4). Although the absorption spectra of 3 and 4 are similar in shape, a significant band shift to longer wavelength is observed for 3. According to the results of DFT calculations, the observed spectroscopic differences are ascribed to differences in the distribution of the MO amplitudes at the α- and β-positions of the TBTAC moiety.

Original language	English
Pages (from-to)	999-1005
Number of pages	7
Journal	Journal of Porphyrins and Phthalocyanines
Volume	13
Issue number	10
DOIs	https://doi.org/10.1142/S1088424609001327
Publication status	Published - 2009 Oct

Keywords

Chlorin
Fullerene
Phthalocyanine

ASJC Scopus subject areas

Chemistry(all)

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10.1142/S1088424609001327

Cite this

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title = "Comparative study of spectroscopic properties of α- Or β-butyloxy-substituted tribenzotetraazachlorin-fullerene conjugates",

abstract = "Mixed condensation of 1,2-dicyanofullerene (1) and 3,6- dibutyloxyphthalonitrile (2a) in the presence of nickel chloride dihydrate (NiCl2·2H2O) in quinoline forms an α-hexabutyloxy-substituted tribenzotetraazachlorin (TBTAC)-fullerene (C60) conjugate (3). UV-vis absorption and magnetic circular dichroism (MCD) properties of 3 have been obtained, and the results compared with those of the β-substituted isomer (4). Although the absorption spectra of 3 and 4 are similar in shape, a significant band shift to longer wavelength is observed for 3. According to the results of DFT calculations, the observed spectroscopic differences are ascribed to differences in the distribution of the MO amplitudes at the α- and β-positions of the TBTAC moiety.",

keywords = "Chlorin, Fullerene, Phthalocyanine",

author = "Takamitsu Fukuda and Hironori Kaneko and Nagao Kobayashi",

note = "Funding Information: This work was partly supported by a Grant-in-Aid for Exploratory Research (No. 18850003) from the Japan Society for the Promotion of Science (JSPS). TF thanks the Intelligent Cosmos Foundation for financial support.",

year = "2009",

month = oct,

doi = "10.1142/S1088424609001327",

language = "English",

volume = "13",

pages = "999--1005",

journal = "Journal of Porphyrins and Phthalocyanines",

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T1 - Comparative study of spectroscopic properties of α- Or β-butyloxy-substituted tribenzotetraazachlorin-fullerene conjugates

AU - Fukuda, Takamitsu

AU - Kaneko, Hironori

AU - Kobayashi, Nagao

N1 - Funding Information: This work was partly supported by a Grant-in-Aid for Exploratory Research (No. 18850003) from the Japan Society for the Promotion of Science (JSPS). TF thanks the Intelligent Cosmos Foundation for financial support.

PY - 2009/10

Y1 - 2009/10

N2 - Mixed condensation of 1,2-dicyanofullerene (1) and 3,6- dibutyloxyphthalonitrile (2a) in the presence of nickel chloride dihydrate (NiCl2·2H2O) in quinoline forms an α-hexabutyloxy-substituted tribenzotetraazachlorin (TBTAC)-fullerene (C60) conjugate (3). UV-vis absorption and magnetic circular dichroism (MCD) properties of 3 have been obtained, and the results compared with those of the β-substituted isomer (4). Although the absorption spectra of 3 and 4 are similar in shape, a significant band shift to longer wavelength is observed for 3. According to the results of DFT calculations, the observed spectroscopic differences are ascribed to differences in the distribution of the MO amplitudes at the α- and β-positions of the TBTAC moiety.

AB - Mixed condensation of 1,2-dicyanofullerene (1) and 3,6- dibutyloxyphthalonitrile (2a) in the presence of nickel chloride dihydrate (NiCl2·2H2O) in quinoline forms an α-hexabutyloxy-substituted tribenzotetraazachlorin (TBTAC)-fullerene (C60) conjugate (3). UV-vis absorption and magnetic circular dichroism (MCD) properties of 3 have been obtained, and the results compared with those of the β-substituted isomer (4). Although the absorption spectra of 3 and 4 are similar in shape, a significant band shift to longer wavelength is observed for 3. According to the results of DFT calculations, the observed spectroscopic differences are ascribed to differences in the distribution of the MO amplitudes at the α- and β-positions of the TBTAC moiety.

KW - Chlorin

KW - Fullerene

KW - Phthalocyanine

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Comparative study of spectroscopic properties of α- Or β-butyloxy-substituted tribenzotetraazachlorin-fullerene conjugates

Abstract

Keywords

ASJC Scopus subject areas

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