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 journalArticle

48 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 languageEnglish
Pages (from-to)2845-2848
Number of pages4
JournalOrganic Letters
Volume5
Issue number16
DOIs
Publication statusPublished - Aug 7 2003

Fingerprint

Fluorine
chemical properties
Chemical properties
fluorine
synthesis
Etioporphyrins
electrons
energy levels
Electrons
Deprotonation
protons
matrices
Electron energy levels
Protons
porphycene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Hayashi, T., Nakashima, Y., Ito, K., Ikegami, T., Aritome, I., Suzuki, A., & Hisaeda, Y. (2003). Synthesis, structure, and chemical property of the first fluorine-containing porphycene. Organic Letters, 5(16), 2845-2848. https://doi.org/10.1021/ol0348452

Synthesis, structure, and chemical property of the first fluorine-containing porphycene. / Hayashi, Takashi; Nakashima, Yuji; Ito, Kazuyuki; Ikegami, Takahiro; Aritome, Isao; Suzuki, Akihiro; Hisaeda, Yoshio.

In: Organic Letters, Vol. 5, No. 16, 07.08.2003, p. 2845-2848.

Research output: Contribution to journalArticle

Hayashi, T, Nakashima, Y, Ito, K, Ikegami, T, Aritome, I, Suzuki, A & Hisaeda, Y 2003, 'Synthesis, structure, and chemical property of the first fluorine-containing porphycene', Organic Letters, vol. 5, no. 16, pp. 2845-2848. https://doi.org/10.1021/ol0348452
Hayashi T, Nakashima Y, Ito K, Ikegami T, Aritome I, Suzuki A et al. Synthesis, structure, and chemical property of the first fluorine-containing porphycene. Organic Letters. 2003 Aug 7;5(16):2845-2848. https://doi.org/10.1021/ol0348452
Hayashi, Takashi ; Nakashima, Yuji ; Ito, Kazuyuki ; Ikegami, Takahiro ; Aritome, Isao ; Suzuki, Akihiro ; Hisaeda, Yoshio. / Synthesis, structure, and chemical property of the first fluorine-containing porphycene. In: Organic Letters. 2003 ; Vol. 5, No. 16. pp. 2845-2848.
@article{a804f86c72e24f2387599295b1dac400,
title = "Synthesis, structure, and chemical property of the first fluorine-containing porphycene",
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.",
author = "Takashi Hayashi and Yuji Nakashima and Kazuyuki Ito and Takahiro Ikegami and Isao Aritome and Akihiro Suzuki and Yoshio Hisaeda",
year = "2003",
month = "8",
day = "7",
doi = "10.1021/ol0348452",
language = "English",
volume = "5",
pages = "2845--2848",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "16",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0141631724&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0141631724&partnerID=8YFLogxK

U2 - 10.1021/ol0348452

DO - 10.1021/ol0348452

M3 - Article

C2 - 12889889

AN - SCOPUS:0141631724

VL - 5

SP - 2845

EP - 2848

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 16

ER -