联杂芳烃型小分子荧光骨架的构筑方法、性质与应用研究

项目名称： 联杂芳烃型小分子荧光骨架的构筑方法、性质与应用研究

项目编号： No.21472127

项目类型： 面上项目

立项/批准年度： 2015

项目学科： 数理科学和化学

项目作者： 高戈

作者单位： 四川大学

项目金额： 86万元

中文摘要： 有机荧光材料的开发研究是当前有机化学的研究热点之一。目前的研究主要集中在对已知骨架的修饰与改造，而具有广泛应用前景的新骨架，由于理论认知的有限，缺乏系统而深入的研究，仍较稀少。同时，人们也难以设计合成具有特定功能的荧光分子。我们发现，一些商品化的和著名的小分子荧光化合物均是由联杂芳烃骨架连接功能基团构成。那么，联杂芳烃骨架是否能成为构筑荧光分子的一个普适策略？本课题将围绕这个问题，发展高效绿色的基于C?H活化的联杂芳烃构筑方法和杂芳烃功能化方法。在此基础之上，采用高通量筛选的办法，通过不同联杂芳烃和功能基的组合，建立全色发光的荧光分子库，寻求结构稳定，荧光性质突出的新型小分子荧光骨架。同时，结合理论计算研究此类分子的构效关系，以期为荧光分子的设计合成提供理论指导。最后，我们期望这些新型的荧光小分子能够在探针、生物标记以及功能材料等方面表现出优异的性能和应用前景。

中文关键词： 联杂芳烃；偶联反应；荧光骨架；探针；有机功能材料

英文摘要： The demanding for organic fluorophors is ever increasing because of the fast development (wide applications) in molecular sensing, bioimaging, optoelectronic devices and functional materials in recent years. The studies and applications of the known skeletons such as courmarin, fluorecein, rhodamine, cyanine and bodipy etc. have made great progresses. Although chemists never stop searching for new fluorogens, rare is comparative with the known ones, except hexaphenylsilole (HPS) and tetraphenylethene (TPE) possessing aggregation-induced emission (AIE) characteristic serendipitously discovered by Tang et al. This is probably because people still know very few about fluorescence and can hardly synthesize fluorogens with designed property. Due to our continuous interests in fluorescent materials, we find that some commercially available and famous fluoregens are all constituted as biheteroarene skeletons with peripheral functional groups. This enlightens us to ask: whether biheteroarene skeleton could be a general strategy to construct fluorogens? In this project, we will try to develop efficient methods for the biheteroarene construction and the functionalization of heteroarenes through C?H activation. These methods will provide us high throughput screening of various fluorogenic molecules and establish a full-colored library, in which stable, highly emissive fluorogens will possibly be found. The DFT theory calculation will then be used to disclose the structure-property relationship in expectation to provide general rules for the fluorogen design. We believe that our study will get a positive answer to the question we ask. Finally, the applications of these new fluorogens will be performed in the field of sensing, bioimaging and functional materials.

英文关键词： biheterocycle;coupling;fluorogen;probe;functional material