Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3- b:3',2'- e]pyridines (BBZFPys)

Ryo Takishima; Yuji Nishii; Tomoaki Hinoue; Yoshitane Imai; Masahiro Miura

doi:10.3762/bjoc.16.32

Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3- b:3',2'- e]pyridines (BBZFPys)

Beilstein J Org Chem. 2020 Mar 6:16:325-336. doi: 10.3762/bjoc.16.32. eCollection 2020.

Authors

Ryo Takishima¹, Yuji Nishii², Tomoaki Hinoue¹, Yoshitane Imai³, Masahiro Miura¹

Affiliations

¹ Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
² Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
³ Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University, Higashi-Osaka, Osaka 577-8502, Japan.

Abstract

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.

Keywords: BINOL; C–H activation; circularly polarized luminescence; palladium.

Grants and funding

This work was supported by JSPS KAKENHI Grant No. JP 19K15586 (Grant-in-Aid for Young Scientists) to Y.N. and JP 17H06092 (Grant-in-Aid for Specially Promoted Research) to M.M.