- Electron Spin Resonance of the Quartet State of 1,3,5-Tris(diphenylamino)benzene
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The electron spin resonance (ESR) of the quartet state of 1,3,5-tris(diphenylamino)benzene (TDAB) is reported.The orange-colored cationic radical is prepared by oxidation of TDAB with trifluoroacetic anhydride in a tetrabutylammonium tetrafluoroborate-CH2Cl2 solution.The ESR spectrum reveals that the cationic radical shows a typical quartet signal and that it is extremely stable at room temperature.
- Yoshizawa, Kazunari,Chano, Akihisa,Ito, Akihiro,Tanaka, Kazuyoshi,Yamabe, Tokio,et al.
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- A periphery cladding strategy to improve the performance of narrowband emitters, achieving deep-blue OLEDs with CIEy < 0.08 and external quantum efficiency approaching 20%
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Deep-blue thermally activated delayed fluorescence (TADF) emitters with National Television System Committee (NTSC) standard (0.14, 0.08) and narrowband emission have been one of the challenging issues for organic light-emitting diodes (OLEDs). In this work, a novel molecular design strategy, periphery cladding, was used to design and synthesize three deep-blue multi-resonance TADF emitters, N,N, 5,9-tetraphenyl-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracen-7-amine (PAB), 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-N,N-diphenyl-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracen-7-amine (2tPAB) and 2,12-di-tert-butyl-N,N,5,9-tetrakis(4-(tert-butyl)phenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracen-7-amine (3tPAB). By cladding large steric hindrance tert-butyl unit at periphery of multi-resonance emitter, the intermolecular interactions were suppressed, thus reducing aggregation-induced emission quenching and improving the PLQY of emitter. 3tPAB with full periphery cladding exhibited higher PLQY (74.7%). As a result, the device based on 3tPAB acquired the best performance by using 1,3-di(9H-carbazol-9-yl)benzene (mCP) with low polarity as host. The maximum external quantum efficiency (EQEmax), CIE coordinates, and full-width at half-maximum (FWHM) of 3tPAB-based device were 19.3%, (0.141, 0.076), and 26 nm, respectively. To our knowledge, this is the first report about narrowband TADF OLEDs with single host that EQEmax approaches 20% while CIE coordinates meet the NTSC blue-light standard.
- Di, Kaiyuan,Duan, Yalei,Guo, Runda,Wang, Lei,Wang, Yaxiong,Ye, Shaofeng,Zhang, Weizhuo,Zhuang, Shaoqing
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- ESR of the cationic triradical of 1,3,5 -tris(diphenylamino )benzene
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The ESR spectrum of the cationic triradical of 1,3,5-tris (diphenylamino)benzene (TDAB) is discussed. The tricautionic state of TDAB was observed by means of cyclic voltammetry. The orange cationic triradical was prepared by oxidation of TDAB with trifluo
- Yoshizawa, Kazunari,Chano, Akihisa,Ito, Akihiro,Tanaka, Kazuyoshi,Yamabe, Tokio,Fujita, Hideo,Yamauchi, Jun,Shiro, Motoo
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- Methyl-substituted Derivatives of 1,3,5-Tris(diphenylamino)benzene as a Novel Class of Amorphous Molecular Materials
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Methyl-substituted derivatives of 1,3,5-tris(diphenylamino)benzene (TDAB) are found to show unique solid-state morphology, as characterized by differential scanning calorimetry and X-ray diffraction.These compounds readily form stable amorphous glasses ha
- Ishikawa, Wataru,Inada, Hiroshi,Nakano, Hideyuki,Shirota, Yasuhiko
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- Mixed er-NHC/phosphine Pd(ii) complexes and their catalytic activity in the Buchwald-Hartwig reaction under solvent-free conditions
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A series of novel (NHC)PdCl2-PR3 complexes were synthesized and fully characterized by 1H, 13C, 31P NMR and FT-IR spectroscopy. These complexes showed high catalytic activity toward solvent-free Buchwald-Hartwig amination. Both primary and secondary amines were efficiently utilized under the same reaction conditions. The solvent-free synthesis of valuable N-aryl carbazoles and similar N-heterocyclic systems was described.
- Ageshina, Alexandra A.,Sterligov, Grigorii K.,Rzhevskiy, Sergey A.,Topchiy, Maxim A.,Chesnokov, Gleb A.,Gribanov, Pavel S.,Nechaev, Mikhail S.,Asachenko, Andrey F.,Bermeshev, Maxim V.,Melnikova, Elizaveta K.
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supporting information
p. 3447 - 3452
(2019/04/30)
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- Heterogeneous aromatic amination of aryl halides with arylamines in water with PS-PEG resin-supported palladium complexes
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Catalytic aromatic amination is achieved in water under heterogeneous conditions by the use of immobilized palladium complexes coordinated with the amphiphilic polystyrene-poly-(ethylene glycol) resin-supported di(tert-butyl)phosphine ligand. Aromatic amination of aryl halides with diphenylamine and N,N-double arylation of anilines with bromobenzene were found to proceed in water with broad substrate tolerance to give the triarylamines in high yield with high recyclability of the polymeric catalyst beads. Very little palladium leached from the polymeric catalyst under the waterbased reaction conditions to provide a green and clean (metal-uncontaminated) protocol for the preparation of triarylamines, including the optoelectronically active N,N,N',N'-tetraaryl-1,1'-biphenyl-4,4'-diamines (TPDs).
- Hirai, Yoshinori,Uozumi, Yasuhiro
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supporting information; experimental part
p. 1788 - 1795
(2011/04/16)
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- Synthesis of 1,3,5-tris[4-(diarylamino)phenyl]benzene and 1,3,5-tris(diarylamino)benzene derivatives
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The title compounds were prepared by the copper catalysed Ullmann coupling of aromatic amines with aromatic aryl iodides. Full spectroscopic details are reported. Solutions of 1,3,5-tris(diarylamino)benzene derivatives in deuterated chloroform undergo hydrogen-deuterium exchange on the central ring and readily turn green owing to partial oxidation by traces of dissolved oxygen. The green colour is quenched by the addition of ascorbic acid. The solutions are more stable in chloroform that has been filtered through basic alumina to remove traces of acid. N-Arylbenzenesulfonamides can be converted to diarylamines by treatment with the sodium salt of an aniline. The Royal Society of Chemistry 2000.
- Plater, M. John,McKay, Murray,Jackson, Toby
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p. 2695 - 2701
(2007/10/03)
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- Cation Radicals of 1,3,5-Tris(diarylamino)benzenes
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Cyclic voltametry and ESR studies reveal the nature of the cation radicals of some 1,3,5-tris(diarylamino)benzenes.Results show effectively delocalized radical cations with long solution lifetimes in cold media but with much less kinetic stability at ambi
- Stickley, Kurt R.,Blackstock, Silas C.
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p. 1585 - 1588
(2007/10/02)
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- STARBURST MOLECULES FOR AMORPHOUS MOLECULAR MATERIALS: SYNTHESIS AND MORPHOLOGY OF 1,3,5-TRIS(DIPHENYLAMINO)BENZENE AND ITS METHYL-SUBSTITUTED DERIVATIVES
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Methyl-substituted derivatives of 1,3,5-tris(diphenylamino)benzene are found to constitute a novel class of amorphous molecular materials, as characterized by differential scanning calorimetry and X-ray diffraction.These compounds readily form stable amor
- Ishikawa, Wataru,Inada, Hiroshi,Nakano, Hideyuki,Shirota, Yasuhiko
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p. 431 - 438
(2007/10/02)
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