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Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys)
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2020-03-06 , DOI: 10.3762/bjoc.16.32
Ryo Takishima , Yuji Nishii , Tomoaki Hinoue , Yoshitane Imai , Masahiro Miura

A series of optically active bisbenzofuro[2,3-b:3’,2’-e]pyridine (BBZFPy) derivatives was synthesized starting with the readily available (S)- and (R)-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 tert-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.

中文翻译:

BINOL衍生的双苯并呋喃[2,3-b:3',2'-e]吡啶(BBZFPys)的合成和圆极化发光性能

从易于获得的(S)-和(R)-1,1'-bi-2开始合成一系列光学活性的双苯并呋喃并[2,3- b:3',2'- e ]吡啶(BBZFPy)衍生物-萘酚通过钯催化的多个分子内C–H / C–H偶联作为关键的闭环步骤。系统地研究了末端丁基取代基对BBZFPy骨架的影响,以揭示固态下独特的聚集诱导的CPL特性增强。还通过单晶X射线分析评估了偶联产物的晶体结构,井然有序的分子间堆叠排列似乎是CPL增强的原因。
更新日期:2020-03-06
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