Fluorescence and chemiluminescence properties of indolylmaleimides: experimental and theoretical studies.
Fluorescence and chemiluminescence properties of indolylmaleimides: experimental and theoretical studies.
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DOI：
10.1039/c003021j
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发表时间：
2010-08
期刊：
影响因子：
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通讯作者：
Manabu Nakazono;Ai Jinguji;S. Nanbu;R. Kuwano;Zilong Zheng;Kenichiro Saita;Yuji Oshikawa;Y. Mikuni-Y.-Miku
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文献类型：
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作者：
Manabu Nakazono;Ai Jinguji;S. Nanbu;R. Kuwano;Zilong Zheng;Kenichiro Saita;Yuji Oshikawa;Y. Mikuni-Y.-Miku
合成了多种吲哚酰马来酰亚胺（IMs），测定了它们的荧光（FL）和化学发光（CL）。吲哚环2位和马来酰亚胺部分3位或4位的取代引起了im的FL和CL的明显变化。观察到IMs的FL几乎是开关开关。在3-（1h -3-吲哚基）-2,5-二氢- 1h -2,5-吡咯二酮中，分子内电荷从吲哚部分转移到马来酰亚胺部分。在im的FL中，CASPT2计算显示吲哚环的NH基团和马来酰亚胺部分在激发态发生去质子化。马来酰亚胺部分的C[双键，长度为m-dash]C键需要在不取代吲哚环2位的情况下在IMs中产生强CL。澄清了聚合物的结构与FL和CL性质的关系。这些结果为IMs作为FL和CL探针的合理设计提供了重要的信息。
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.