多取代咔唑衍生物EMCC的合成及光谱学性质  

Synthesis and Spectral Properties of Ethyl 1-Methyl-9H-carbazole-2-carboxylate

作　　者：赵霜 曾星 吴佳鑫 马越 杜玉英[2] ZHAO Shuang;ZENG Xing;WU Jiaxin;MA Yue;DU Yuying(College of Science,Inner Mongolia Agricultural University,Hohhot 010018,China;Chemical Engineering College,Inner Mongolia University of Technology,Hohhot 010051,China)

机构地区：[1]内蒙古农业大学理学院,呼和浩特010018 [2]内蒙古工业大学化工学院,呼和浩特010051

出　　处：《内蒙古农业大学学报（自然科学版）》2024年第5期77-82,共6页Journal of Inner Mongolia Agricultural University(Natural Science Edition)

基　　金：内蒙古自治区高等学校科学研究项目(NJZY20051);内蒙古工业大学博士基金项目(BS2021023);内蒙古工业大学大学生创新创业训练计划项目(2023053004);内蒙古自治区自然科学基金项目(2023LHMS02011)。

摘　　要：本文以2-乙酰基-4,4-二乙氧基丁酸乙酯和吲哚为原料,通过[4+2]环化反应合成了A-π-D型荧光化合物1-甲基-9H-咔唑-2-甲酸乙酯(EMCC),其结构经NMR、IR和MS进行了表征。研究了化合物EMCC在CH_(3)CN、C_(2)H_(5)OH、CHCl_(3)、THF、DMF、CH_(3)OH、CH_(2)Cl_(2)溶剂中的紫外光谱、荧光光谱及Stokes位移等光谱性能。通过Lippert方程和Bakhshiev's方程研究了其溶剂极性函数与Stokes位移之间的关系。研究结果表明,EMCC的光谱学特性受到溶剂极性的显著影响。随着溶剂极性的增加,其荧光最大发射峰向长波长方向移动,从379 nm红移至412 nm,具有明显的溶剂效应。采用密度泛函理论计算了化合物EMCC的HOMO和LUMO轨道能级,能级差为4.14 eV,可为咔唑衍生物荧光材料的开发提供参考。A novelπ-conjugate A-π-D structure compound,i.e.,Ethyl 1-methyl-9H-carbazole-2-carboxylate(EMCC),was synthesized by[4+2]annulation reaction of indole with ethyl 2-acetyl-4,4-diethoxybutanoate.The structure of EMCC was characterized by the NMR,IR and MS.The photophysical properties of the fluorophore EMCC was investigated in CH_3CN,C_2H_5OH,CHCl_3,THF,DMF,CH_3OH,CH_2Cl_(2)by the UV-Vis absorption,emission and Stokes shift.The variation of Stoke's shift with F_1(ε,n)was described by using the Lippert equation for EMCC.The results showed that the effects of solvent polarity on absorption and fluorescence spectra were evident.With the increase of solvent polarity,the maximum emission peak of fluorescence shifted to the direction of long wavelength,from 379 nm to 412 nm.DFT calculations were used for the analysis of the frontier molecular orbital of EMCC.The results could facilitate the development of fluorescence materials on carbazole derivatives.

关 键 词：1-甲基-9H-咔唑-2-甲酸乙酯 荧光 溶剂效应 理论计算 

分 类 号：O626.3[理学—有机化学]