基于二炔烃串联环化构筑荧光稠环化合物

Design and synthesis of fluorescent fused arenes, heterocyclic arenes based on the cascade cyclization of various diynes were proposed. Cascade cyclizations of diynes could be triggered by electrophiles or transition metals. Dehydrogenative Dieles-Alder reactions could also be used to construct the arenes from designed diynes with fluorescent property. By determining and calculating the photophysical properties of these synthesized arenes in different states, such as dilute solution, aggregates, powder, and crystal, we would like to summarize and establish some fluorescent structure-property relationship and apply them in the further design of new fluorophores. Moreover, we will apply these arenes in the fields of optoelectronics and fluorescent chemosensors.

本项目将运用二炔烃亲电串联环化、脱氢环加成、过渡金属催化下的串联环化等合成策略，通过二炔烃底物结构的设计，合成具有潜在荧光发射性能的稠环、稠杂环化合物；在测定它们稀溶液、聚集体、粉末、晶体状态下光物理性能的基础上，结合一定的理论计算，建立和发展基于稠环、稠杂环化合物的荧光构效关系，发展这些新荧光分子作为有机光电材料和荧光探针的应用。

基于合成新方法，合成了一系列具有独特荧光性能的新稠环化合物，通过光物理性能测试和理论计算等方法，研究了新稠环化合物的荧光构效关系，并发展了它们作为荧光化学传感和材料的应用。发展了苄腈作为氰基化试剂，实现了对多种底物（如芳烃、芳基卤代烃、芳基硼酸酯等）的氰基化；利用苄腈，合成了3-氰基咪唑[1,2-a]吡啶类化合物，简化了抗焦虑药沙立吡旦（Saripidem）和麻醉药奈可吡旦（Necopidem）的合成路线；利用苄腈，合成了新荧光稠环化合物，如2-芳基-3-氰基苯并呋喃，量子效率高达88.9%。基于C-H活化/稠环反应，以烯酮亚胺为耦合物种，合成了3-二芳亚甲基异吲哚啉类化合物，并发现这类物质具有聚集荧光增强效应、力致变色等特征。