The synthesis of robust, polymeric hole-transport materials from oligoarylamine substituted styrenes

McKeown, Neil B.; Badriya, Samer; Helliwell, Madeleine; Shkunov, Maxim

doi:10.1039/b614235d

Cited by 27 publications

(19 citation statements)

References 37 publications

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“…The nitrogen atom is sp 2 hybridized, π‐conjugated with rings i and ii but not iii , as reflected also in C–N distances. A similar conformation was observed in unsubstituted phenothiazine (θ = 158.5°),21 N ‐phenylphenothiazine (θ = 162.6 and 150.7°),22 N ‐(4‐vinylphenyl)phenothiazine (θ = 154.5 and 148.1°)23 and N ‐(4‐bromophenyl)‐phenothiazine (θ = 144.9 and 150.8°) 24. Although substantial differences of θ between symmetrically independent molecules in the last three structures indicate its “softness” towards crystal packing effects, phenothiazine folding mainly depends on the bond geometry at the S and N atoms 25.…”

Section: Resultssupporting

confidence: 62%

Synthesis and characterization of fluorene‐based oligomers and polymers incorporating N‐arylphenothiazine‐S,S‐dioxide units

Kamtekar¹,

Dahms

Batsanov

et al. 2011

J. Polym. Sci. A Polym. Chem.

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A series of 3,7-bis(9,9-din -hexylfluoren-2-yl)-N-arylphenothiazine-S,S-dioxide trimers and (9,9-din -octylfluorene-2,7-diyl-coN -arylphenothiazine-S,S-dioxide) co-polymers, with varying ratios of phenothiazine-S,S-dioxide units, have been prepared in good yields by palladium-catalyzed cross-coupling reactions. The materials are deep blue emitters and show no solvatochromism or evidence for an intramolecular chargetransfer state. The photoluminescence quantum yields of the trimers are U PL 15-30% in solution and 14-25% in films. The polymers demonstrated very high values in solution (U PL 74-84%) and U PL values in films of 28-47%. The estimated HOMO energy levels are between À5.64 and À5.62 eV for the polymers with 15% incorporation of the phenothiazine-S,S-dioxide units. An analogous N-arylphenothiazine co-polymer shows significantly red shifted absorption and emission. Solution electrochemical data and density functional theory calculations are also presented. V

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Section: Resultssupporting

confidence: 62%

Synthesis and characterization of fluorene‐based oligomers and polymers incorporating N‐arylphenothiazine‐S,S‐dioxide units

Kamtekar¹,

Dahms

Batsanov

et al. 2011

J. Polym. Sci. A Polym. Chem.

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“…The absorption spectra of the dyes in solution and adsorbed on TiO 2 films were measured with a Jasco-570 UV/vis spectrophotometer. The precursor compounds 1-3 (Scheme 1) and the acceptor moieties were synthesized according to the literature procedures [20][21][22][23]. Cyclic voltammetry experiments of the dyes were performed in SAMA 500 electroanalyzer system, SAMA research center, Iran, with a Pt working electrode, a Pt counter electrode, an Ag/AgCl reference electrode, and a scan rate of 0.1 V/s at room temperature under nitrogen in a CH 2 Cl 2 solution that included 0.1 M tetrabutylammonium hexafluorophosphate.…”

Section: General Methodsmentioning

confidence: 99%

New tetrazole-based organic dyes for dye-sensitized solar cells

Chermahini

Dabbagh

et al. 2015

Journal of Energy Chemistry

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“…The solvent was evaporated to obtain a colorless solid (9.36 g, 98%): m.p. 165-166 8C; 1 H NMR (400 MHz,CDCl 3 ,1 H;ArH);3 H;ArH),4 H;ArH),1 H;ArH),4 H;ArH); 13 19 H 13 BrN 2 : C 65.35,H 3.75,N 8.02;found: C 65.40,H 3.65,N 7.79.…”

Section: Methodsmentioning

confidence: 99%

“…As starting materials dibromobenzaldehyde 13 and the diiodo compound 14 were used. [13] Suzuki coupling and further Wittig reaction of 15 and 16 yielded the dendritically structured monomers 10 and 11 in moderate yields (Scheme 2).…”

Section: Syntheses and Characterizationmentioning

confidence: 99%

Charge‐Transporting Polymers based on Phenylbenzoimidazole Moieties

Debeaux

Thesen

Schneidenbach

et al. 2010

Adv Funct Materials

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A series of novel styrene functionalized monomers with phenylbenzo[d]imidazole units and the corresponding homopolymers are prepared. These side‐chain polymers show high glass‐transition temperatures that even exceed the corresponding value for the common electron‐transporting material 1,3,5‐tris(1‐phenyl‐1H‐benzo[d]imidazol‐2‐yl)benzene (TPBI). Similar electronic behavior between the polymers and TPBI is shown. The polymers are used as matrices for phosphorescent dopants. The fabricated devices exhibit current efficiencies up to 38.5 cd A−1 at 100 cd m−2 and maximum luminances of 7400 cd m−2 at 10 V with a minimum turn‐on voltage as low as 2.70 V in single‐layer devices with an ITO/PEDOT:PSS anode (ITO = indium tin oxide, PEDOT:PSS = poly(3,4‐ethylenedioxythiophene) doped with poly(styrenesulfonate)) and a CsF/Ca/Ag cathode.

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The synthesis of robust, polymeric hole-transport materials from oligoarylamine substituted styrenes

Cited by 27 publications

References 37 publications

Synthesis and characterization of fluorene‐based oligomers and polymers incorporating N‐arylphenothiazine‐S,S‐dioxide units

Synthesis and characterization of fluorene‐based oligomers and polymers incorporating N‐arylphenothiazine‐S,S‐dioxide units

New tetrazole-based organic dyes for dye-sensitized solar cells

Charge‐Transporting Polymers based on Phenylbenzoimidazole Moieties

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