4-(4-(5-甲酰基-2-噻吩基)苯基)-2,2′∶6′,2″-三联吡啶的合成、表征及其光学性质  

Synthesis,Characterization and Optical Properties of 4-(4-(5-Formyl-2-thienyl)phenyl-2,2′∶6′,2″-terpyridine

作　　者：唐稳 吴军蓉 季时宇 刘昭第 郝扶影 TANG Wen;WU Junrong;JI Shiyu;LIU Zhaodi;HAO Fuying(College of Chemical and Materials Engineering,Fuyang Normal University,Fuyang 236000,China)

机构地区：[1]阜阳师范大学化学与材料工程学院,安徽阜阳236000

出　　处：《合成化学》2024年第11期944-950,972,共8页Chinese Journal of Synthetic Chemistry

基　　金：安徽省教育厅研究生质量工程项目(2023jyjxggyjY210,2023zyxwjxalk130);国家自然科学基金资助项目(21701025);安徽省高校自然科学项目(2022AH051314,KJ2021ZD0075);大学生创新创业计划项目(S02310371017)。

摘　　要：三联吡啶衍生物及其金属配合物在光电化学和生物医学等领域具有广泛的应用,一直以来是研究的热点之一。本文通过2种不同途径合成了4-(4-(5-甲酰基-2-噻吩基)苯基)-2,2′∶6′,2″-三联吡啶(3),其结构经1 H NMR,13 C NMR,IR和MS-ESI表征。研究表明:在相同条件下,通过Suzuki偶联反应,方法2:(4-硼酸苯基)-2,2′∶6′,2″-三联吡啶(1b)与5-溴噻吩-2-甲醛(2b)反应比方法1:(4-溴苯基)-2,2′∶6′,2″-三联吡啶(1a)与5-醛基-2-噻吩硼酸(2a)反应的产率高。通过紫外-可见光谱、荧光光谱初步探讨了化合物3与三联吡啶中间体(1a,1b)的光学性质,结果表明:由于噻吩环与醛基的存在,与中间体1a和1b相比,目标产物3的荧光强度最高,光学性质最好。Tripyridine derivatives and their metal complexes have been one of the popular directions due to a wide range of applications in the fields of photoelectrochemistry,biomedicine,etc.In this paper,4-(4-(5-formyl-2-thienyl)phenyl-2,2′∶6′,2″-terpyridine(3)was synthesized and confirmed by 1 H NMR,13 C NMR,IR,and MS-ESI.Using two different routes[Method 2:(4-boronic acid phenyl)-2,2′∶6′,2″-terpyridine(1b),with 5-bromothiophene-2-carbaldehyde(2b)by Suzuki coupling reaction was performed in higher yields than method 1:(4-bromophenyl)-2,2′∶6′,2″-terpyridine(1a)with 5-aldehyde-2-thiopheneboronic acid(2a)].A preliminary investigation of the optical properties of compound 3 and the terpyridine intermediates(1a,1b)were conducted using UV-Vis spectroscopy and fluorescence spectroscopy.The results indicated that 3 exhibited the highest fluorescence intensity compared to intermediates 1a and 1b,due to the presence of the thiophene ring and the aldehyde group.

关 键 词：SUZUKI偶联 三联吡啶衍生物 钯催化剂 溶剂化效应 

分 类 号：O621.22[理学—有机化学]