Takishima Ryo, Nishii Yuji, Hinoue Tomoaki, Imai Yoshitane, Miura Masahiro
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Beilstein J Org Chem. 2020 Mar 6;16:325-336. doi: 10.3762/bjoc.16.32. eCollection 2020.
A series of optically active bisbenzofuro[2,3-:3',2'-]pyridine (BBZFPy) derivatives was synthesized starting with the readily available ()- and ()-1,1'-bi-2-naphthols through a palladium-catalyzed multiple intramolecular C-H/C-H coupling as the key ring-closure step. The effect of terminal -butyl substituents on the BBZFPy skeleton was systematically investigated to uncover a unique aggregation-induced enhancement of CPL characteristics in the solid state. The crystal structures of the coupling products were also evaluated by single crystal X-ray analysis and the well-ordered intermolecular stacking arrangements appeared to be responsible for the enhanced CPL.
以易于获得的（+）-和（-）-1,1'-联-2-萘酚为起始原料，通过钯催化的多分子内C-H/C-H偶联作为关键的闭环步骤，合成了一系列旋光性双苯并呋喃[2,3-:3',2'-]吡啶（BBZFPy）衍生物。系统研究了BBZFPy骨架上末端叔丁基取代基的影响，以揭示固态下圆偏振发光（CPL）特性独特的聚集诱导增强效应。还通过单晶X射线分析评估了偶联产物的晶体结构，有序的分子间堆积排列似乎是CPL增强的原因。
