新型硒二唑衍生物荧光分子的合成及光电性能研究  

Synthesis and Photoelectric Properties of Novel Fluorescent Molecules of Selenodiazole Derivatives

作　　者：江凡 蒋振涛 林升大 张贤慧 黄雯孝 黄薛龙 JIANG Fan;JIANG Zhentao;LIN Shengda;ZHANG Xianhui;HUANG Wenxiao;HUANG Xuelong(Key Laboratory of Prevention and Treatment of Cardiovascular and Cerebrovascular Diseases,Ministry of Education,College of Pharmacy Gannan Medical University,Ganzhou 341000,China;Key Laboratory of Radioactive and Rare Scattered Minerals,Ministry of Land and Resources Guangdong Institute of Mineral Applications,Shaoguan 512026,China)

机构地区：[1]赣南医学院心脑血管疾病防治教育部重点实验室药学院,江西赣州341000 [2]广东省矿产应用研究所国土资源部放射性与稀有稀散矿产重点实验室,广东韶关512026

出　　处：《合成化学》2022年第10期771-776,共6页Chinese Journal of Synthetic Chemistry

基　　金：国土资源部放射性与稀有稀散矿产重点实验室开发课题(RRSM-KF2018-05);心脑血管疾病防治教育部重点实验室开放课题(XN202009);江西省高校人文社会科学研究青年项目(JY21236);2021年江西省大学生创新创业训练计划项目(S202110413018)。

摘　　要：为了增大前期工作开发中Hg^(2+)荧光探针分子TBBA在近红外区间的吸收范围,降低分子的生物组织损耗,本研究在保持三苯胺为给电子单元不变的情况下,将苯并噻二唑分子换成吸电子能力更强的苯并硒二唑和吡啶硒二唑单元,并通过Suzuki偶联反应合成了两种新型荧光分子TBSeBA和TPSeBA。经过核磁共振氢谱、碳谱和ESI质谱确认了两种分子的结构,在DMSO溶液中TBSeBA和TPSeBA的吸收峰分别位于465.00 nm和520.00 nm。TBSeBA的HOMO和LUMO能级分别为-5.00 eV和-2.82 eV;TPSeBA的HOMO和LUMO能级分别为-5.17 eV和-2.77 eV。硒原子的引入为荧光分子的光学性质和电化学性质调控提供了一种有效策略。In order to optimize the absorption performance of fluorescent probe TBBA developed in the previous work and reduce the loss of biological tissues,the benzothiadiazole unit in the molecule was replaced with benzoseladiazole and pyridineseladiazole units with stronger electron-withdrawing ability.Two new fluorescent molecules TBSeBA and TPSeBA are synthesized through Suzuki coupling reaction.The two molecular structures were confirmed by proton nuclear magnetic resonance spectroscopy,carbon spectroscopy and ESI mass spectrometry.The absorption peaks of TBSeBA and TPSeBA in DMSO solution are 465.00 nm and 520.00 nm,respectively.The HOMO and LUMO orbital energy of TBSeBA are-5.00 eV and-2.82 eV,respectively,and the HOMO and LUMO orbital energy of TPSeBA are-5.17 eV and-2.77 eV,respectively.The above result shows that the introduction of selenium atoms provides an effective strategy for the regulation of the optical properties and electrochemical properties of fluorescent molecules.

关 键 词：三苯胺 苯并硒二唑 吡啶硒二唑 近红外 荧光分子 合成 光电性能 

分 类 号：O62[理学—有机化学]