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Syntheses of Diverse Donor-Substituted Bisbenzofuro[2,3-b:3’,2’- e]pyridines (BBZFPys) via Pd Catalysis, and Their Photophysical Properties

Itai, Yuhei; Nishii, Yuji; Stachelek, Patrycja; Data, Przemyslaw; Takeda, Youhei; Minakata, Satoshi; Miura, Masahiro

Syntheses of Diverse Donor-Substituted Bisbenzofuro[2,3-b:3’,2’- e]pyridines (BBZFPys) via Pd Catalysis, and Their Photophysical Properties Thumbnail


Authors

Yuhei Itai

Yuji Nishii

Patrycja Stachelek

Przemyslaw Data

Youhei Takeda

Satoshi Minakata

Masahiro Miura



Contributors

Abstract

A series of bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys) bearing a chlorine functionality have been efficiently synthesized through a Pd-catalyzed double oxidative intramolecular C–H/C–H coupling of mono-chlorinated 2,6-diaryloxypyridines. The subsequent Buchwald-Hartwig amination of the chlorinated BBZFPys allowed for the access to a new class of donor-acceptor (D-A) π-conjugated compounds that comprise of BBZFPy as an electron-acceptor (A) and diarylamines as a donor (D) units. The investigation of the steady-state photophysical properties of the prepared D-A compounds revealed that they are emissive in both of solution and solid states in blue-to-green color region. The singlet-triplet energy splitting (DEST) was found much smaller than that of substituent- free BBZFPy (0.70 eV), ranging from 0.01 to 0.56 eV. The time-resolved spectroscopy revealed that the D-A compounds comprising of a bis(tert-butyl)carbazole as the D and CF3-attached BBZFPy as the A showed delayed fluorescence (DF) in a non-polar matrix host material (Zeonex®), while in a polar matrix (DPEPO), room-temperature phosphorescence (RTP) was faintly observed. Furthermore, organic light-emitting diodes (OLEDs) fabricated with the D-A compounds as a blue-emitter showed a moderate external quantum efficiencies (EQEs) up to 1.5%.

Citation

Itai, Y., Nishii, Y., Stachelek, P., Data, P., Takeda, Y., Minakata, S., & Miura, M. (2018). Syntheses of Diverse Donor-Substituted Bisbenzofuro[2,3-b:3’,2’- e]pyridines (BBZFPys) via Pd Catalysis, and Their Photophysical Properties. Journal of Organic Chemistry, 83(17), 10289-10302. https://doi.org/10.1021/acs.joc.8b01451

Journal Article Type Article
Acceptance Date Jun 7, 2018
Online Publication Date Aug 13, 2018
Publication Date Sep 7, 2018
Deposit Date Aug 15, 2018
Publicly Available Date Mar 29, 2024
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 83
Issue 17
Pages 10289-10302
DOI https://doi.org/10.1021/acs.joc.8b01451

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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of organic chemistry copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.8b01451





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