2',7'-二卤代荧光素的pH敏感性及其光稳定性  

Dependence of 2',7'-Dihalofluorescein on pH and Their Photostability

作　　者：陈鹏[1] 葛凤燕[1] 吴猛[1] 田魏成 蔡再生[1] 

机构地区：[1]东华大学化学化工与生物工程学院,上海201620

出　　处：《精细化工》2014年第3期388-393,408,共7页Fine Chemicals

基　　金：国家自然科学基金青年科学基金项目(51203018);国家自然科学基金面上项目(21171034)~~

摘　　要：该文采用Diels-Alder反应,以4-卤代(氟、氯、溴)间苯二酚与邻苯二甲酸酐为原料,在甲基磺酸催化剂作用下合成了2',7'-二卤代荧光素(DFF、DCF、DBF)。对化合物的结构进行了表征。pH滴定实验表明,化合物(DFF、DCF、DBF)的紫外吸收与荧光发射光谱均对溶液的pH有较强的敏感性。DFF、DCF、DBF分别在490、502、505 nm处的吸收强度和在517、526、530 nm处的荧光强度均随着pH增加而增大;当溶液的pH>10,其吸收强度与荧光强度基本保持不变。DFF、DCF和DBF的热力学常数pKa值随着卤族元素的原子序数的增加依次增大,分别是4.7、5.1、6.6;其荧光量子产率依次减小,分别是0.97、0.94、0.67。光降解实验结果表明,化合物的光稳定性大小依次是DFF>DCF>FL(荧光素)>DBF。In this paper ,2＇ ,7 ＇-dihalofluorescein（ DFF, DCF and DBF） were synthesized by Diels-Alder reaction of 4-haloresorcinol with phthalic anhydride in the presence of methanesulfonic acid as catalyzer,and their structures were characterized. The pH titrations indicate that the dependence of fluorescent properties of these compounds on pH was extremely sensitive in the absorption spectra and the fluorescence spectra. The absorption intensities at 490,502 and 505 nm, and the fluorescent intensities at 517,526 and 530 nm in DFF,DCF and DBF increased with pH increasing,respectively. When pH 〉 10, the absorption intensities and fluorescent intensities kept constant. The thermodynamic pKa values of DFF, DCF and DBF were 4.7,5.1 and 6.6, and the fluorescence quantum yields of DFF, DCF and DBF were 0. 97,0.94 and 0.67, respectively. The photodegradation experiment indicates the photostability was in the descending order of DFF 〉 DCF 〉 FL 〉 DBF.

关 键 词：二卤代荧光素 PH敏感性 光稳定性 荧光量子产率 特种染料与颜料 

分 类 号：TQ617.3[化学工程—精细化工]