Song Shengmei, Ju Dong, Li Junfen, Li Duxin, Wei Yanli, Dong Chuan, Lin Peihua, Shuang Shaomin
Research Center of Environmental Science and Engineering, Department of Chemistry, Shanxi University, Shanxi 030006, PR China.
Talanta. 2009 Mar 15;77(5):1707-14. doi: 10.1016/j.talanta.2008.10.008. Epub 2008 Oct 17.
The synthesis and absorption/fluorescence properties of two novel intramolecular charge transfer (ICT) compounds of (fluorene-2-yl)-(9-ethylcarbazole-3-yl) ketene and 1-phenyl-3-(fluorenone-2-yl)-5-(9-ethylcarbazole-3-yl)-2-pyrazoline were reported. The primary structure of the target compounds was characterized by IR and (1)H NMR. The systems contained a fluorenone or a propenon group as an electron acceptor (A) and an N-ethylcarbazole and a pyrazoline group as electron donors (D). From the emissive properties it was concluded that the electronic coupling between D and A was sufficient to allow charge transfer in these molecules. The ICT maximal emission displayed a large wavelength shift and Stokes shifts increased in response to the increase of the solvent polarity. The highly solvatochromic properties made the two compounds of great interest as new classes of fluorescent probes, electroluminescent and electrofax materials.
报道了两种新型分子内电荷转移（ICT）化合物芴-2-基-（9-乙基咔唑-3-基）乙烯酮和1-苯基-3-（芴酮-2-基）-5-（9-乙基咔唑-3-基）-2-吡唑啉的合成及其吸收/荧光性质。通过红外光谱和¹H核磁共振对目标化合物的一级结构进行了表征。该体系包含一个芴酮或一个丙烯酮基团作为电子受体（A），以及一个N-乙基咔唑和一个吡唑啉基团作为电子供体（D）。从发射性质得出结论，D和A之间的电子耦合足以使这些分子中发生电荷转移。ICT最大发射显示出较大的波长位移，并且斯托克斯位移随着溶剂极性的增加而增大。高度的溶剂化显色性质使得这两种化合物作为新型荧光探针、电致发光和静电复印材料具有很大的研究价值。
