UV-vis absorption and fluorescence spectra, solvatochromism, and application to pH sensors of novel xanthene dyes having thienyl and thieno[3,2-b]thienyl rings as auxochrome
UV-vis absorption and fluorescence spectra, solvatochromism, and application to pH sensors of novel xanthene dyes having thienyl and thieno[3,2-b]thienyl rings as auxochrome
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DOI：
10.1016/j.dyepig.2016.11.013
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发表时间：
2017-04
影响因子：
4.5
通讯作者：
M. Matsui;Takaya Yamamoto;Kenta Kakitani;Siddanagouda M Biradar;Y. Kubota;K. Funabiki
中科院分区：
文献类型：
--
作者：
M. Matsui;Takaya Yamamoto;Kenta Kakitani;Siddanagouda M Biradar;Y. Kubota;K. Funabiki
合成了含噻吩基和噻吩并[3，2-B]噻吩环的新型氧杂蒽染料。在二氯甲烷中的紫外-可见吸收最大值为助色剂的顺序：NEt 2（罗丹明B，558 nm）< 2-噻吩基（569 nm）< 5-噻吩并[3，2-B]噻吩基（608 nm）。这些新的咕吨染料仅在非氢键接受溶剂如氯仿和二氯甲烷中着色。噻吩基和噻吩并[3，2-B]噻吩基衍生物的内酯前体通过加入pKa值分别低于-2.2和0.23的强酸而着色，而罗丹明B的内酯前体通过加入pKa值低于4.7的弱酸而着色。这些结果源于杂芳族化合物的有色阳离子染料的稳定性低于二乙基氨基助色剂。
Novel xanthene dyes having thienyl and thieno[3,2-b]thienyl rings as auxochrome have been synthesized. The UV–vis absorption maximum in dichloromethane was in the order of the auxochrome: NEt2(Rhodamine B, 558 nm) < 2-thienyl (569 nm) < 5-thieno[3,2-b]thienyl (608 nm). These new xanthene dyes colored only in non-hydrogen-bond accepting solvents such as chloroform and dichloromethane. The lactone precursors of the thienyl and thieno[3,2-b]thienyl derivatives colored by adding strong acids whose pKa value is lower than −2.2 and 0.23, respectively, whereas that of rhodamine B colored by adding weak acids whose pKa value is lower than 4.7. These results originate from less stability of colored cationic dyes by the heteroaromatics than by the diethylamino auxochrome.