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

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...

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Published inBeilstein journal of organic chemistry Vol. 16; no. 1; pp. 325 - 336
Main Authors Takishima, Ryo, Nishii, Yuji, Hinoue, Tomoaki, Imai, Yoshitane, Miura, Masahiro
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 06.03.2020
Beilstein-Institut
Subjects
binol
Chemistry
circularly polarized luminescence
c–h activation
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Optical properties
Palladium
Pyridines
BINOL
palladium
C–H activation
circularly polarized luminescence
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.16.32