Year

2020

Type(s)

Journal Article

Author(s)

Izumi, S. and Higginbotham, H.F. and Nyga, A. and Stachelek, P. and Tohnai, N. and Silva, P.D. and Data, P. and Takeda, Y. and Minakata, S.

Source

Journal of the American Chemical Society, 142(3): 1482—1491, 2020

Url

https://www.scopus.com/inward/record.uri?eid=2-s2.0-85078534558&doi=10.1021%2fjacs.9b11578&partnerID=40&md5=393967e1f5763531d1640a017c409af9

BibTeX

BibTeX

BibTeX

@ARTICLE{Izumi20201482, author={Izumi, S. and Higginbotham, H.F. and Nyga, A. and Stachelek, P. and Tohnai, N. and Silva, P.D. and Data, P. and Takeda, Y. and Minakata, S.}, title={Thermally Activated Delayed Fluorescent Donor-Acceptor-Donor-Acceptor π-Conjugated Macrocycle for Organic Light-Emitting Diodes}, journal={Journal of the American Chemical Society}, year={2020}, volume={142}, number={3}, pages={1482-1491}, doi={10.1021/jacs.9b11578}, note={cited By 0}, url={https://www.scopus.com/inward/record.uri?eid=2-s2.0-85078534558&doi=10.1021%2fjacs.9b11578&partnerID=40&md5=393967e1f5763531d1640a017c409af9}, affiliation={Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871, Japan; Department of Material and Life Science, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871, Japan; School of Chemistry, Monash University, Clayton, VIC 3800, Australia; Faculty of Chemistry, Silesian University of Technology, M. Strzody 9, Gliwice, 44-100, Poland; Physics Department, Durham University, South Road, Durham, DH1 3LE, United Kingdom; Department of Energy Conversion and Storage, Technical University of Denmark, Anker Engelunds Vej 301, Kongens Lyngby, 2800, Denmark; Center of Polymer and Carbon Materials, Polish Academy of Sciences, M. Curie-Sklodowskiej 34, Zabrze, 41-819, Poland}, abstract={A new class of thermally activated delayed fluorescent donor-acceptor-donor-acceptor (D-A-D-A) π-conjugated macrocycle comprised of two U-shaped electron-acceptors (dibenzo[a,j]phenazine) and two electron-donors (N,N′-diphenyl-p-phenyelendiamine) has been rationally designed and successfully synthesized. The macrocyclic compound displayed polymorphs-dependent conformations and emission properties. Comparative studies on physicochemical properties of the macrocycle with a linear surrogate have revealed significant effects of the structural cyclization of the D-A-repeating unit, including more efficient thermally activated delayed fluorescence (TADF). Furthermore, an organic light-emitting diode (OLED) device fabricated with the macrocycle compound as the emitter has achieved a high external quantum efficiency (EQE) up to 11.6%, far exceeding the theoretical maximum (5%) of conventional fluorescent emitters and that with linear analogue (6.9%). Copyright © 2020 American Chemical Society.}, keywords={Electronic equipment; Fluorescence; Physicochemical properties, Comparative studies; Donor acceptor donors; Emission properties; External quantum efficiency; Fluorescent emitters; Macrocyclic compounds; Thermally activated; Thermally activated delayed fluorescences, Organic light emitting diodes (OLED), dibenzo[a,j]phenazine; macrocyclic compound; n,n' diphenyl 4 phenyelendiamine; unclassified drug, absorption; absorption spectroscopy; Article; comparative study; conformation; controlled study; cyclization; density functional theory; external quantum efficiency; fluorescence; macrocyclization; photoluminescence; photoluminescence spectra; physical chemistry; quantum mechanics; single crystal X ray crystallography; spectroscopy; synthesis; thermally activated delayed fluorescence; time resolved spectroscopy; ultraviolet visible absorption spectroscopy; ultraviolet visible spectroscopy; X ray crystallography}, funding_details={Japan Society for the Promotion of ScienceJapan Society for the Promotion of Science, JSPS, JP17H05155}, funding_details={European CommissionEuropean Commission, EC}, funding_details={Fundacja na rzecz Nauki PolskiejFundacja na rzecz Nauki Polskiej, FNP}, funding_details={European Regional Development FundEuropean Regional Development Fund, FEDER, TEAM 2017-4/32 POIR.04.04.00-00-4668/17-00}, funding_details={Horizon 2020Horizon 2020, 778158}, funding_text 1={This research was supported by the Grant-in-Aid for Scientific Research on Innovative Areas “π-System Figuration: Control of Electron and Structural Dynamism for Innovative Functions” (JSPS KAKENHI Grant no. JP17H05155 to Y.T.), “Aquatic Functional Materials: Creation of New Materials Science for Environment-Friendly and Active Functions” (JSPS KAKENHI Grant no. JP19H05716 to Y.T.), and the Continuation Grants for Young Researchers from the Asahi Glass Foundation (to Y.T.). P.D. and A.N. acknowledge the kind support received from the First Team program of the Foundation for Polish Science cofinanced by the European Union under the European Regional Development Fund (project number: First TEAM 2017-4/32 POIR.04.04.00-00-4668/17-00). Y.T. and P.D. acknowledge the EU’s Horizon 2020 for funding the OCTA project under grant agreement no. 778158. We acknowledge the experimental support of Professors Kei Tsujimoto (Osaka University) and Hiroshi Uyama (Osaka University) for the DSC measurement.}, references={Rochat, S., Swager, T.M., Conjugated Amplifying Polymers for Optical Sensing Applications (2013) ACS Appl. Mater. 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