一种新型二氰基异氟尔酮荧光材料的合成及其光谱特性  

Synthesis of a Novel Dicyanoisophorone-Based Fluorophore and Its Spectral Characteristic

作　　者：顾小敏 赵俊豪 张艺欣 姜大炜 冯燕 钮珊珊 GU Xiaomin;ZHAO Junhao;ZHANG Yixin;JIANG Dawei;FENG Yan;NIU Shanshan(College of Life Science and Chemistry,Jiangsu Sencond Normal University,Nanjing 210013,China)

机构地区：[1]江苏第二师范学院生命科学与化学化工学院,江苏南京210013

出　　处：《山东化工》2025年第6期133-136,共4页Shandong Chemical Industry

基　　金：江苏省高校自然科学基金面上项目(22KJB150021);大学生创新创业训练项目(202414436284J)资助。

摘　　要：以异氟尔酮为起始原料,先与丙二腈进行缩合,合成二氰基异氟尔酮,再与对乙酰氨基苯甲醛进行克脑文盖尔缩合反应,中间体经过盐酸水解后,合成2-[3-(4-氨基苯乙烯基)-5,5-二甲基环己-2-烯-1-亚基]丙二腈,最后与2-溴乙胺溴酸盐反应,合成一种新型的二氰基异氟尔酮荧光染料,产物及中间体通过核磁以及高分辨质谱确证,并利用紫外分光光度计和荧光光谱仪探究其光谱性能,结果表明该染料的最大发射波长为650 nm,位于近红外区,且具有大的斯托克斯位移(225 nm)。在乙腈中,染料的吸光度与浓度具有较好的线性关系(R^(2)=0.99885),进一步探究其在七种不同溶剂中的荧光发射光谱,可知在磷酸缓冲溶液(PBS)中,荧光强度最强,表明染料在荧光探针领域具有较好的应用前景,可进一步拓展其在电致发光、生物造影和生物医药领域的应用。The product was synthesized from isophorone,It is first condensed with malononitrile to synthesize dicyanoisophorone,and then reacted with N-(4-formylphenyl)acetamide,which was then hydrolyzed in the presence of muriatic acid to obtain 2-(3-(4-aminostyryl)-5,5-dimethylcyclohex-2-enylidene)malononitrile,Finally,a novel dicyanoisophorone-based fluorescence dye was obtain from the reaction with 2-bromo-ethylamin hydrobromide.The product and intermediates were elucidated by NMR and HRMS.The preliminary study on its spectral characteristic was investigated which showed that the dye exhibited an emission maximum of 655 nm with large stokes shift(225 nm).The intermediate in acetone has a good linear relationship between the absorption and concentration of the dye(R^(2)=0.99885).Further exploration of its fluorescence emission spectra in seven different solvents showed that the strongest fluorescence intensity was obtained in phosphate buffered saline(PBS),indicating that the dye had good application prospects in the field of fluorescent probes and could further expand its applications in electroluminescence,bio imaging,and biomedicine.

关 键 词：二氰基异氟尔酮 丙二腈 紫外 荧光 

分 类 号：O629.1[理学—有机化学]