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
Full Research Paper
Information storage
Optical properties
Palladium
Pyridines
BINOL
palladium
C–H activation
circularly polarized luminescence
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Abstract 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.
AbstractList 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.
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.
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.
Author Miura, Masahiro
Nishii, Yuji
Imai, Yoshitane
Hinoue, Tomoaki
Takishima, Ryo
AuthorAffiliation 3 Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University, Higashi-Osaka, Osaka 577-8502, Japan
2 Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
1 Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/32256850$$D View this record in MEDLINE/PubMed
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Issue 1
Keywords BINOL
palladium
C–H activation
circularly polarized luminescence
Language English
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Snippet A series of optically active bisbenzofuro[2,3- :3',2'- ]pyridine (BBZFPy) derivatives was synthesized starting with the readily available ( )- and (...
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...
A series of optically active bisbenzofuro[2,3-b:3’,2’-e]pyridine (BBZFPy) derivatives was synthesized starting with the readily available (S)- and...
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SubjectTerms binol
Chemistry
circularly polarized luminescence
c–h activation
Full Research Paper
Information storage
Optical properties
Palladium
Pyridines
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Title Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3- b :3',2'- e ]pyridines (BBZFPys)
URI https://www.ncbi.nlm.nih.gov/pubmed/32256850
https://www.proquest.com/docview/2396547827/abstract/
https://search.proquest.com/docview/2387696200
https://pubmed.ncbi.nlm.nih.gov/PMC7082704
https://doaj.org/article/95ab65c0311f44b48f7cb06ec0348112
Volume 16
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