Year

2018

Type(s)

Journal Article

Author(s)

Itai, Y. and Nishii, Y. and Stachelek, P. and Data, P. and Takeda, Y. and Minakata, S. and Miura, M.

Source

Journal of Organic Chemistry, 83(17): 10289—10302, 2018

Url

https://www.scopus.com/inward/record.uri?eid=2-s2.0-85052319589&doi=10.1021%2facs.joc.8b01451&partnerID=40&md5=ec18b7629a01dec8da9fe9b20548c7b8

BibTeX

BibTeX

BibTeX

@ARTICLE{Itai201810289, author={Itai, Y. and Nishii, Y. and Stachelek, P. and Data, P. and Takeda, Y. and Minakata, S. and Miura, M.}, title={Syntheses of Diverse Donor-Substituted Bisbenzofuro[2,3- b:3′,2′- e]pyridines (BBZFPys) via Pd Catalysis, and Their Photophysical Properties}, journal={Journal of Organic Chemistry}, year={2018}, volume={83}, number={17}, pages={10289-10302}, doi={10.1021/acs.joc.8b01451}, note={cited By 3}, url={https://www.scopus.com/inward/record.uri?eid=2-s2.0-85052319589&doi=10.1021%2facs.joc.8b01451&partnerID=40&md5=ec18b7629a01dec8da9fe9b20548c7b8}, affiliation={Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871, Japan; Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871, Japan; Durham University, Physics Department, South Road, Durham, DH1 3LE, United Kingdom; Faculty of Chemistry, Silesian University of Technology, M. Strzody 9, Gliwice, 44-100, Poland; Center of Polymer and Carbon Materials, Polish Academy of Sciences, M. Curie-Sklodowskiej 34, Zabrze, 41-819, Poland}, 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 monochlorinated 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 BBZFPy as an electron acceptor (A) and diarylamines as a donor (D) unit. The investigation of the steady-state photophysical properties of the prepared D-A compounds revealed that they are emissive in both solution and solid states in the blue-to-green color region. The singlet-triplet energy splitting (ΔEST) was found to be 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 a bis(tert-butyl)carbazole as the D and CF3-attached BBZFPy as the A, showed delayed fluorescence (DF) in nonpolar 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%. Copyright © 2018 American Chemical Society.}, keywords={Amines; Catalysis; Fluorescence; Laser spectroscopy; Organic light emitting diodes (OLED); Organic polymers; Pyridine, Delayed fluorescence; Donor-acceptors; Electron acceptor; External quantum efficiency; Organic light emitting diodes(OLEDs); Photophysical properties; Room temperature phosphorescence; Time-resolved spectroscopy, Palladium}, references={Krug, M., Erlenkamp, G., Sippl, W., Schächtele, C., Totzke, F., Milgeroth, A., Discovery and Selectivity-Profiling of 4-Benzylamino 1-Aza-9-oxafluorene Derivatives as Lead Structures for IGF-1R Inhibitors (2010) Bioorg. Med. Chem. 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