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

doi:10.1039/C003021J

Fluorescence and chemiluminescence properties of indolylmaleimides: experimental and theoretical studies†‡

Manabu Nakazono,*^a Ai Jinguji,^a Shinkoh Nanbu,^b Ryoichi Kuwano,^c Zilong Zheng,^bd Kenichiro Saita,^bc Yuji Oshikawa,^a Yuta Mikuni,^c Tatsuhiro Murakami,^b Yi Zhao,^e Shigeki Sasaki^a and Kiyoshi Zaitsu^a

Author affiliations

* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan
E-mail: nakazono@phar.kyushu-u.ac.jp

^b Faculty of Science and Technology, Sophia University, 7-1 Kioi-Cho, Chiyoda-ku, Tokyo 102-8554, Japan

^c Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

^d Department of Chemical Physics, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China

^e State Key Laboratory of Physical Chemistry of Solid Surfaces and Department of Chemistry, Xiamen University, Xiamen, P. R. China

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 [double bond, length as m-dash] 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.

Physical Chemistry Chemical Physics

Fluorescence and chemiluminescence properties of indolylmaleimides: experimental and theoretical studies†‡

Abstract

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Fluorescence and chemiluminescence properties of indolylmaleimides: experimental and theoretical studies

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