杂原子多环芳烃的合成

摘要

以2-己基-1-癸醇(2)为起始原料,依次经Appel反应、Williamson反应、溴取代反应、Suzuki偶联反应、三聚反应、Scholl氧化脱氢关环反应得到含硫原子的目标化合物1a.采用类似合成方法,合成目标化合物1b.这些化合物的结构均通过核磁共振(1H NMR)和基质辅助激光解吸电离飞行时间质谱(MALDI-TOF MS)表征,并对其光谱特征、热性能及电学性能进行了初步的研究.从紫外荧光光谱中可知这类化合物在甲苯中呈现砖红色荧光,可作为一种新型的砖红色主体发光材料,用于荧光传感器等光电材料.热失重分析结果表明这类化合物热稳定性良好,有望应用于对热稳定性要求较高的有机纳米器件.另外,由循环伏安曲线可知此类杂原子多环芳烃是强电子供体,在光伏器件中有着潜在的应用前景.%2-hexy-1-decanol (2) was used as starting material,followed by Appel reaction,Williamson reaction,Bromine substitution reaction,Suzuki coupling reaction,Trimerization reaction,and Scholl cyclodehydrogenation reaction to obtain the S-doped target compound 1a.The similar synthesis method was used to obtain the target compound 1b.The structures of these compounds were characterized by nuclear magnetic resonance (1H NMR) and matrix-assisted laser desorption/lonization time of flight mass spectrometry(MALDI-TOF MS),and their spectral characteristics,thermal and electrical properties were investigated.The ultraviolet and fluorescence emission spectra shows that these compounds exhibit brick red fluorescence in toluene,and can be used as a new type of brick red luminescent material for fluorescent materials such as fluorescence sensors.Thermogravimetric analysis results suggest that they have high thermal stability,which can be applied to organic nano devices with high thermal stability requirements.In addition,cyclic voltammetry indicates that the heteroatom polycyclic aromatic hydrocarbons (PAHs) are strong donors and have potential applications in photovoltaic devices in the future.