Fluorescent Dyes with 2-Amino-4,7-diazaindole Skeleton: Synthesis and Spectroscopy
作者:Daniel T. Gryko、Joanna Piechowska、Volha Vetokhina、Dominik Wójcik
DOI:10.1246/bcsj.82.1514
日期:2009.12.15
The reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with compounds possessing two vicinal chlorine atoms activated toward nucleophilic substitution has been studied. All derivatives bearing a 2,3-dichloropyrazine moiety react with DBU leading to fluorescent dyes. Among others, only 2,3-dichloro-1,4-naphthoquinone reacts giving the expected pentacyclic product albeit in a very low yield and accompanied by the product of hydrolysis. Spectroscopic properties of the synthesized compounds were studied. The dye formed from 5,6-dichloro-2,3-dicyanopyrazine exhibits a very high Stokes shift and strong dependence of the fluorescence quantum yield on solvent polarity.
我们研究了 1,8-二氮杂双环[5.4.0]十一-7-烯(DBU)与具有两个邻位氯原子的化合物的反应。所有含有 2,3-二氯吡嗪分子的衍生物都会与 DBU 发生反应,生成荧光染料。其中,只有 2,3-二氯-1,4-萘醌会发生反应,产生预期的五环产物,尽管产率非常低,而且伴有水解产物。对合成化合物的光谱特性进行了研究。由 5,6-二氯-2,3-二氰基吡嗪形成的染料表现出很高的斯托克斯偏移,荧光量子产率与溶剂极性有很大关系。