具有D-A构型的噻吩基三联吡啶的设计合成、晶体结构及其生物显影应用  

Design,Synthesis,Crystal Structure and Bioimaging Application of Thienyl Terpyridine with D-A Configuration

作　　者：孟飞[1] MENG Fei(Department of Food and Environmental Engineering,Chuzhou Polytechnic,Chuzhou Anhui 239000,China)

机构地区：[1]滁州职业技术学院食品与环境工程学院,安徽滁州239000

出　　处：《西华师范大学学报（自然科学版）》2021年第3期278-283,共6页Journal of China West Normal University(Natural Sciences)

基　　金：安徽省教育厅自然科学研究重点项目(KJ20191127);安徽省教育厅自然科学研究重大项目(KJ2017ZD49);安徽省教学示范课《精细化工生产技术》项目(1872);滁州职业技术学院人才项目(ZD2021005)。

摘　　要：以易制备、溶解度好且具有芳香性的噻吩衍生物作为供电子基团,平面性好的β-三联吡啶作为吸电子基团,设计合成了一种具有D-A构型的噻吩基三联吡啶衍生物(MF)。通过现代分析技术手段(核磁共振氢谱、碳谱、质谱和单晶X射线衍射)对其进行系统的表征,晶体结构分析表明,分子具有良好的平面性,较为合适的电子离域能力和丰富的分子间作用力有利于整个分子内电荷转移,为其光学性质奠定了良好的基础。通过吸收、发射光谱、理论计算和稳态发射光谱系统研究了MF的光学性质,MF在475~500 nm具有较强的荧光发射峰(量子产率为12%),且发射寿命为3.34 ns。生物研究发现,MF对HeLa细胞具有较低的毒性,并能够有效着色溶酶体,有望作为溶酶体荧光探针被进一步探索。A thienyl-terpyridine derivatives(MF)with D-A configuration is designed and synthesized by introducing a thiophene derivative of easy preparation,good solubility and aromaticity as the electron-donating group andβ-terpyridine of good planarity as the electron-withdrawing group.It is systematically characterized by modern analytical techniques,including^(1)H NMR,^(13)C NMR,HRMS and SCXRD.The crystal structure analysis shows that the molecule possesses good planarity,relatively suitable electron delocalization ability and abundant intermolecular forces interactions forces interactions of molecular benefit to intramolecalar charge transfer,laying a good foundation for its optical properties.The optical properties of MF are systematically studied by absorption spectrum,emission spectrum,theoretical calculations and steady-state emission spectrum,which shows a strong fluorescence emission peak around 475~500 nm(quantum yield 12%),and the enission lifetime is 3.45 ns.Biological studies have found that the MF is of low toxicity to HeLa cells and effective target of lysosomes.It is expected to be further explored as a lysosomal fluorescent probe.

关 键 词：D-A构型 噻吩基三联吡啶衍生物 晶体结构 光学性质 溶酶体荧光探针 

分 类 号：O622.6[理学—有机化学]