Fluorescence and chemiluminescence properties of indolylmaleimides

Experimental and theoretical studies

Manabu Nakazono, Ai Jinguji, Shinkoh Nanbu, Ryoichi Kuwano, Zilong Zheng, Kenichiro Saita, Yuji Oshikawa, Yuta Mikuni, Tatsuhiro Murakami, Yi Zhao, Shigeki Sasaki, Kiyoshi Zaitsu

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Various indolylmaleimides (IMs) were synthesized, and their fluorescence (FL) and chemiluminescence (CL) were measured. The substitution at the 2-position of the indole ring and the 3- or 4-position of the maleimide moiety caused an obvious change in the FL and CL of the IMs. An almost on-off switching of the FL of the IMs was observed. The intramolecular charge transfer from the indole moiety to the maleimide moiety occurred in 3-(1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione. In the FL of the IMs, CASPT2 calculations showed deprotonation of the NH group of the indole ring and the maleimide moiety at the excited state. The C=C bond in the maleimide moiety was needed for strong CL in the IMs without substitution at the 2-position of the indole ring. The relationships between the FL or CL properties and the structures of the IMs were clarified. These results provide significant information on the rational design of IMs as FL and CL probes.

Original languageEnglish
Pages (from-to)9783-9793
Number of pages11
JournalPhysical Chemistry Chemical Physics
Volume12
Issue number33
DOIs
Publication statusPublished - Jan 1 2010

Fingerprint

Chemiluminescence
chemiluminescence
Fluorescence
indoles
fluorescence
rings
Substitution reactions
substitutes
Deprotonation
Excited states
Charge transfer
charge transfer
indole
maleimide
probes
excitation

All Science Journal Classification (ASJC) codes

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

Cite this

Fluorescence and chemiluminescence properties of indolylmaleimides : Experimental and theoretical studies. / Nakazono, Manabu; Jinguji, Ai; Nanbu, Shinkoh; Kuwano, Ryoichi; Zheng, Zilong; Saita, Kenichiro; Oshikawa, Yuji; Mikuni, Yuta; Murakami, Tatsuhiro; Zhao, Yi; Sasaki, Shigeki; Zaitsu, Kiyoshi.

In: Physical Chemistry Chemical Physics, Vol. 12, No. 33, 01.01.2010, p. 9783-9793.

Research output: Contribution to journalArticle

Nakazono, M, Jinguji, A, Nanbu, S, Kuwano, R, Zheng, Z, Saita, K, Oshikawa, Y, Mikuni, Y, Murakami, T, Zhao, Y, Sasaki, S & Zaitsu, K 2010, 'Fluorescence and chemiluminescence properties of indolylmaleimides: Experimental and theoretical studies', Physical Chemistry Chemical Physics, vol. 12, no. 33, pp. 9783-9793. https://doi.org/10.1039/c003021j
Nakazono, Manabu ; Jinguji, Ai ; Nanbu, Shinkoh ; Kuwano, Ryoichi ; Zheng, Zilong ; Saita, Kenichiro ; Oshikawa, Yuji ; Mikuni, Yuta ; Murakami, Tatsuhiro ; Zhao, Yi ; Sasaki, Shigeki ; Zaitsu, Kiyoshi. / Fluorescence and chemiluminescence properties of indolylmaleimides : Experimental and theoretical studies. In: Physical Chemistry Chemical Physics. 2010 ; Vol. 12, No. 33. pp. 9783-9793.
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