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Issue 33, 2010
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Fluorescence and chemiluminescence properties of indolylmaleimides: experimental and theoretical studies

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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.

Graphical abstract: Fluorescence and chemiluminescence properties of indolylmaleimides: experimental and theoretical studies

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Publication details

The article was received on 12 Feb 2010, accepted on 21 Apr 2010 and first published on 22 Jun 2010


Article type: Paper
DOI: 10.1039/C003021J
Phys. Chem. Chem. Phys., 2010,12, 9783-9793

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    Fluorescence and chemiluminescence properties of indolylmaleimides: experimental and theoretical studies

    M. Nakazono, A. Jinguji, S. Nanbu, R. Kuwano, Z. Zheng, K. Saita, Y. Oshikawa, Y. Mikuni, T. Murakami, Y. Zhao, S. Sasaki and K. Zaitsu, Phys. Chem. Chem. Phys., 2010, 12, 9783
    DOI: 10.1039/C003021J

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