Peroxyoxalate chemiluminescence of N,N′-bistosyl-1H,4H-quinoxaline-2,3-dione and related compounds. Dependence on electronic nature of fluorophores

Jiro Motoyoshiya, Nobuaki Sakai, Minoru Imai, Yuka Yamaguchi, Ryu Koike, Yutaka Takaguchi, Hiromu Aoyama

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The title compound N,N′-bistosyl-1H,4H-quinoxaline-2,3-dione (TsQD) provides peroxyoxalate chemiluminescence (PO-CL) when reacted with hydrogen peroxide in the presence of fluorophores. The chemiluminescence (CL) efficiency of TsQD was superior to that of other related compounds such as bis(2,4,6-trichlorophenyl) oxalate (TCPO), a typical oxalate for the peroxyoxalate PO-CL, under an aqueous condition. Factors affecting the PO-CL efficiency are discussed from the viewpoint of the structures of the substrates and the electronic nature of the fluorophores. A linear correlation of the logarithmic values evaluated from the CL quantum yields with the oxidation potentials of the aromatic fluorophores supports the involvement of the chemically initiated electron exchange luminescence (CIEEL) mechanism in both TsQD- and TCPO-CL systems. Also, an excellent Hammett relationship was derived from the correlation between the σ+ values and the relative singlet excitation yields in TsQD-CL enhanced by a series of fluorescent para,para′-disubstituted distyrylbenzenes.

Original languageEnglish
Pages (from-to)7314-7318
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number21
DOIs
Publication statusPublished - Oct 18 2002
Externally publishedYes

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Quinoxalines
Chemiluminescence
Fluorophores
Oxalates
Quantum yield
peroxyoxalate
Hydrogen Peroxide
Luminescence
Oxidation
Electrons
Substrates

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Peroxyoxalate chemiluminescence of N,N′-bistosyl-1H,4H-quinoxaline-2,3-dione and related compounds. Dependence on electronic nature of fluorophores. / Motoyoshiya, Jiro; Sakai, Nobuaki; Imai, Minoru; Yamaguchi, Yuka; Koike, Ryu; Takaguchi, Yutaka; Aoyama, Hiromu.

In: Journal of Organic Chemistry, Vol. 67, No. 21, 18.10.2002, p. 7314-7318.

Research output: Contribution to journalArticle

Motoyoshiya, Jiro ; Sakai, Nobuaki ; Imai, Minoru ; Yamaguchi, Yuka ; Koike, Ryu ; Takaguchi, Yutaka ; Aoyama, Hiromu. / Peroxyoxalate chemiluminescence of N,N′-bistosyl-1H,4H-quinoxaline-2,3-dione and related compounds. Dependence on electronic nature of fluorophores. In: Journal of Organic Chemistry. 2002 ; Vol. 67, No. 21. pp. 7314-7318.
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abstract = "The title compound N,N′-bistosyl-1H,4H-quinoxaline-2,3-dione (TsQD) provides peroxyoxalate chemiluminescence (PO-CL) when reacted with hydrogen peroxide in the presence of fluorophores. The chemiluminescence (CL) efficiency of TsQD was superior to that of other related compounds such as bis(2,4,6-trichlorophenyl) oxalate (TCPO), a typical oxalate for the peroxyoxalate PO-CL, under an aqueous condition. Factors affecting the PO-CL efficiency are discussed from the viewpoint of the structures of the substrates and the electronic nature of the fluorophores. A linear correlation of the logarithmic values evaluated from the CL quantum yields with the oxidation potentials of the aromatic fluorophores supports the involvement of the chemically initiated electron exchange luminescence (CIEEL) mechanism in both TsQD- and TCPO-CL systems. Also, an excellent Hammett relationship was derived from the correlation between the σ+ values and the relative singlet excitation yields in TsQD-CL enhanced by a series of fluorescent para,para′-disubstituted distyrylbenzenes.",
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AU - Takaguchi, Yutaka

AU - Aoyama, Hiromu

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