氟代二苯乙烯氨基酸的合成及性能  

Synthesis and Properties of Fluostilbenic Amino Acids

作　　者：郑林波 赵孔娥 朱芳芳 胡晓松 ZHENG Lin-bo;ZHAO Kong-e;ZHU Fang-fang;HU Xiao-song(School of Chemistry,Chemical Engineering and Life Sciences,Wuhan University of Technology,Wuhan 430070,China)

机构地区：[1]武汉理工大学化学化工与生命科学学院,湖北武汉430070

出　　处：《合成化学》2020年第4期270-276,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金面上项目(21472144);武汉理工大学自主创新研究基金资助项目(2018-IB-024)。

摘　　要：以4-碘-L-苯丙氨酸为初始原料,经羧基和氨基的保护得到化合物2;化合物2与4-氟苯乙烯进行Heck反应得化合物3;化合物3脱去保护基得氟代二苯乙烯氨基酸(4,47.4%);其结构经1H NMR,13C NMR,IR和MS(ESI-TOF)确证。光学性质研究结果表明:4的激发、发射波长分别为314 nm和355 nm,斯托克斯位移为41 nm,荧光量子产率为0.22。化合物4在甲醇溶液中存在光致顺反异构现象,反式→顺式结构转变速率常数为0.026 min^-1。Compound 2 was prepared from 4-iodo-L-phenylalanine via the protection of carboxyl and amino groups.Compound 3 was synthesized by the Heck reaction of 2 with 4-fluorostyrene,which was then deprotected to afford fluorostilbenic amino acid(4,47.4%).The structure of 4 was confirmed by 1H NMR,13C NMR,IR and MS(ESI-TOF).In addition,its optical property was studied.The results show that the excitation and emission wavelengths of 4 are 314 nm and 355 nm,respectively.The Stokes shift of it is 41 nm,and the quantum yield is 0.22.The photo-induced cis/trans isomerization of compound 4 in methanol solution was observed.The trans to cis isomerization rate is determined to be 0.026 min^-1 by UV-Vis.The 19F NMR spectra of compound 4 show that the chemical shifts of the fluorine atoms in the trans and cis structures are-115.22 and-115.53,respectively.

关 键 词：氟代二苯乙烯氨基酸 合成 荧光探针 光致异构 量子产率 

分 类 号：O621.3[理学—有机化学] O657.3[理学—化学]