基于苯并噻二唑的非共价构型锁定稠环小分子的合成与性能研究

Research of the synthesis and properties of benzthiadiazole-based non-covalent conformational locking small molecular

近年来,稠环化合物在有机光电材料领域取得了显著成效。我们利用Still coupling和Knoevengel缩合等经典有机反应,设计合成了以苯并噻二唑(BT)为中心核,吸电子基团(二氰基亚甲基)靛酮(IC)、5,6-二氟-3-(二氰基亚甲基)靛酮(IC4F)为端基的两个新型共轭非共价键稠环小分子化合物BT2T-IC和BT2T-IC4F。一方面,通过S…O和O…H等作用在分子内形成非共价键构象锁促进分子的平面性;另一方面,通过增加端基的缺电子性可以增强分子内的电荷迁移。在二者的协同作用下,两个新型小分子化合物的光谱吸收拓宽到近红外区,这有利于获得宽的光谱响应。其化学结构通过核磁共振氢谱和碳谱予以证实。通过紫外-可见吸收光谱、电化学循环伏安法及密度泛函理论(DFT)计算对其光物理对其光物理和电化学性质进行了实验研究。

In recent years,fused-ring compounds have achieved remarkable results in the field of organic optoelectronic materials.In this paper,two novel benzothiadiazole(BT)–based conjugated non-covalently bonded ring small molecular compounds with the electron-absorbing groups fluorine and cyanogroup as ending-group,namely BT2T-IC and BT2T-IC4F,were synthesized successfully by Still coupling and Knoevengel condensation reaction,respectively.On the one hand,S…O and O…H can be used to form non-covalent bond conformation lock in molecules to promote the planarity of molecules.On the other hand,intramolecular charge transfer can be enhanced by increasing the electron-lack of the end group.Under the synergistic action,the spectral absorption of the two new small molecular compounds is broadened to the near infrared region,which is conducive to obtaining a wide spectral response.Their molecular structures were characterized by NMR,and their photophysics and electrochemical properties were investigated by density functional theory(DFT)calculations,UV-vis absorption spectroscopy and cyclic voltammetry experiments.