Synthesis and spectroscopic investigation of trifluoroethoxy-coated phthalocyanine linked with fullerene

Daisuke Sukeguchi; Hideyuki Yoshiyama; Norio Shibata; Shuichi Nakamura; Takeshi Toru; Yasuhiko Hayashi; Tetsuo Soga

doi:10.1016/j.jfluchem.2008.11.005

Synthesis and spectroscopic investigation of trifluoroethoxy-coated phthalocyanine linked with fullerene

Daisuke Sukeguchi, Hideyuki Yoshiyama, Norio Shibata, Shuichi Nakamura, Takeshi Toru, Yasuhiko Hayashi, Tetsuo Soga

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

30 Citations (Scopus)

Abstract

Synthesis and spectroscopic investigation of trifluoroethoxy-coated phthalocyanine-fullerene dyad 2 has been described. While nonfluorinated phthalocyanine-fullerene dyad 1 showed an efficient property of intramolecular photoinduced electron transfer, dyad 2, regardless of its covalently linked dyad system, appears not to show any electronic communication between fullerene and phthalocyanine. This observation is presumably due to the strong electron withdrawing nature of 12 trifluoroethoxy groups; fluorine leads phthalocyanine to become an acceptor whose electronic accepting property is equivalent to that of fullerene. This is a unique example that fluorine can terminate electronic communication in the covalently fullerene-phthalocyanine dyad system.

Original language	English
Pages (from-to)	361-364
Number of pages	4
Journal	Journal of Fluorine Chemistry
Volume	130
Issue number	3
DOIs	https://doi.org/10.1016/j.jfluchem.2008.11.005
Publication status	Published - Mar 2009
Externally published	Yes

Keywords

Aggregation
Donor-acceptor dyads
Fluorine effects
Fullerenes
Phthalocyanines

ASJC Scopus subject areas

Biochemistry
Environmental Chemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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Synthesis and spectroscopic investigation of trifluoroethoxy-coated phthalocyanine linked with fullerene. / Sukeguchi, Daisuke; Yoshiyama, Hideyuki; Shibata, Norio; Nakamura, Shuichi; Toru, Takeshi; Hayashi, Yasuhiko; Soga, Tetsuo.

In: Journal of Fluorine Chemistry, Vol. 130, No. 3, 03.2009, p. 361-364.

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

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title = "Synthesis and spectroscopic investigation of trifluoroethoxy-coated phthalocyanine linked with fullerene",

abstract = "Synthesis and spectroscopic investigation of trifluoroethoxy-coated phthalocyanine-fullerene dyad 2 has been described. While nonfluorinated phthalocyanine-fullerene dyad 1 showed an efficient property of intramolecular photoinduced electron transfer, dyad 2, regardless of its covalently linked dyad system, appears not to show any electronic communication between fullerene and phthalocyanine. This observation is presumably due to the strong electron withdrawing nature of 12 trifluoroethoxy groups; fluorine leads phthalocyanine to become an acceptor whose electronic accepting property is equivalent to that of fullerene. This is a unique example that fluorine can terminate electronic communication in the covalently fullerene-phthalocyanine dyad system.",

keywords = "Aggregation, Donor-acceptor dyads, Fluorine effects, Fullerenes, Phthalocyanines",

author = "Daisuke Sukeguchi and Hideyuki Yoshiyama and Norio Shibata and Shuichi Nakamura and Takeshi Toru and Yasuhiko Hayashi and Tetsuo Soga",

note = "Funding Information: This work was supported by the Incorporated Administrative Agency New Energy and Industrial Technology Development Organization (NEDO) under the Ministry of Economy, Trade and Industry (METI), and Nagase Science and Technology Foundation. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.",

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doi = "10.1016/j.jfluchem.2008.11.005",

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AU - Sukeguchi, Daisuke

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AU - Nakamura, Shuichi

AU - Toru, Takeshi

AU - Hayashi, Yasuhiko

AU - Soga, Tetsuo

N1 - Funding Information: This work was supported by the Incorporated Administrative Agency New Energy and Industrial Technology Development Organization (NEDO) under the Ministry of Economy, Trade and Industry (METI), and Nagase Science and Technology Foundation. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.

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N2 - Synthesis and spectroscopic investigation of trifluoroethoxy-coated phthalocyanine-fullerene dyad 2 has been described. While nonfluorinated phthalocyanine-fullerene dyad 1 showed an efficient property of intramolecular photoinduced electron transfer, dyad 2, regardless of its covalently linked dyad system, appears not to show any electronic communication between fullerene and phthalocyanine. This observation is presumably due to the strong electron withdrawing nature of 12 trifluoroethoxy groups; fluorine leads phthalocyanine to become an acceptor whose electronic accepting property is equivalent to that of fullerene. This is a unique example that fluorine can terminate electronic communication in the covalently fullerene-phthalocyanine dyad system.

AB - Synthesis and spectroscopic investigation of trifluoroethoxy-coated phthalocyanine-fullerene dyad 2 has been described. While nonfluorinated phthalocyanine-fullerene dyad 1 showed an efficient property of intramolecular photoinduced electron transfer, dyad 2, regardless of its covalently linked dyad system, appears not to show any electronic communication between fullerene and phthalocyanine. This observation is presumably due to the strong electron withdrawing nature of 12 trifluoroethoxy groups; fluorine leads phthalocyanine to become an acceptor whose electronic accepting property is equivalent to that of fullerene. This is a unique example that fluorine can terminate electronic communication in the covalently fullerene-phthalocyanine dyad system.

KW - Aggregation

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KW - Fluorine effects

KW - Fullerenes

KW - Phthalocyanines

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Synthesis and spectroscopic investigation of trifluoroethoxy-coated phthalocyanine linked with fullerene

Abstract

Keywords

ASJC Scopus subject areas

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