Synthesis, structure, and chemical property of the first fluorine-containing porphycene

Takashi Hayashi; Yuji Nakashima; Kazuyuki Ito; Takahiro Ikegami; Isao Aritome; Akihiro Suzuki; Yoshio Hisaeda

doi:10.1021/ol0348452

Synthesis, structure, and chemical property of the first fluorine-containing porphycene

Takashi Hayashi, Yuji Nakashima, Kazuyuki Ito, Takahiro Ikegami, Isao Aritome, Akihiro Suzuki, Yoshio Hisaeda

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

53 Citations (Scopus)

Abstract

(Matrix presented) A pyrrolic macrocycle, β -tetrakis(trifluoromethyl)porphycene, is the first example of a fluorine-containing porphycene. Four electron-withdrawing CF₃ substituents provide a highly distorted structure and an attractive electron-deficient nature for the porphycene framework. From the electrochemical study, it is found that the LUMO energy level for the β-trifluoromethylporphycene is 1.24 V more stabilized compared to that for etioporphyrin. Moreover, the deprotonation of the inner N-H proton in the porphycene was observed upon the addition of DBU.

Original language	English
Pages (from-to)	2845-2848
Number of pages	4
Journal	Organic letters
Volume	5
Issue number	16
DOIs	https://doi.org/10.1021/ol0348452
Publication status	Published - Aug 7 2003

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Matrix presented) A pyrrolic macrocycle, β -tetrakis(trifluoromethyl)porphycene, is the first example of a fluorine-containing porphycene. Four electron-withdrawing CF3 substituents provide a highly distorted structure and an attractive electron-deficient nature for the porphycene framework. From the electrochemical study, it is found that the LUMO energy level for the β-trifluoromethylporphycene is 1.24 V more stabilized compared to that for etioporphyrin. Moreover, the deprotonation of the inner N-H proton in the porphycene was observed upon the addition of DBU.",

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T1 - Synthesis, structure, and chemical property of the first fluorine-containing porphycene

AU - Hayashi, Takashi

AU - Nakashima, Yuji

AU - Ito, Kazuyuki

AU - Ikegami, Takahiro

AU - Aritome, Isao

AU - Suzuki, Akihiro

AU - Hisaeda, Yoshio

PY - 2003/8/7

Y1 - 2003/8/7

N2 - (Matrix presented) A pyrrolic macrocycle, β -tetrakis(trifluoromethyl)porphycene, is the first example of a fluorine-containing porphycene. Four electron-withdrawing CF3 substituents provide a highly distorted structure and an attractive electron-deficient nature for the porphycene framework. From the electrochemical study, it is found that the LUMO energy level for the β-trifluoromethylporphycene is 1.24 V more stabilized compared to that for etioporphyrin. Moreover, the deprotonation of the inner N-H proton in the porphycene was observed upon the addition of DBU.

AB - (Matrix presented) A pyrrolic macrocycle, β -tetrakis(trifluoromethyl)porphycene, is the first example of a fluorine-containing porphycene. Four electron-withdrawing CF3 substituents provide a highly distorted structure and an attractive electron-deficient nature for the porphycene framework. From the electrochemical study, it is found that the LUMO energy level for the β-trifluoromethylporphycene is 1.24 V more stabilized compared to that for etioporphyrin. Moreover, the deprotonation of the inner N-H proton in the porphycene was observed upon the addition of DBU.

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Synthesis, structure, and chemical property of the first fluorine-containing porphycene

Abstract

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