Oxidative coupling polymerization of 4-methyltriphenylamine

Oginö, Kazuhíde; Kanegae, Aiko; Yamaguchi, Ryoji; Sato, Hisaya; Kurjata, Jan

doi:10.1002/(sici)1521-3927(19990301)20:3<103::aid-marc103>3.0.co;2-q

Cited by 72 publications

(44 citation statements)

References 10 publications

(14 reference statements)

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“…There were 15 intense resonances due to 1 methyl carbon and 14 aromatic carbons. Aromatic regions of13 C NMR and DEPT45 spectra and assignment of PDNTA are depicted in Figure 7. The DEPT45 spectrum shows that the signals at 148.41, 144.94, 135.64, 134.59, 130.33, and 130.20 ppm are the quaternary carbons.…”

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confidence: 99%

Synthesis and Properties of Poly[di(1-naphthyl)-4-tolylamine] as a Hole Transport Material

Nomura¹,

Shibasaki²,

Ueda³

et al. 2004

Macromolecules

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A novel hole-transporting poly[di(1-naphthyl)-4-tolylamine:DNTA] (PDNTA) has been developed. PDNTA was easily prepared by oxidative coupling polymerization of DNTA using FeCl3 as an oxidant. This polymerization produced regiocontrolled PDNTA with high molecular weights. PDNTA exhibited strong UV-vis absorption bands at 267 and 370 nm in chloroform solution. Their photoluminescence spectra showed a maximum peak band around 445-448 nm in the blue region. The organic light-emitting device (OLED) prepared by spin-casting PDNTA solution onto ITO-coated glass substrate in conjunction with Alq and LiF/Al, as an electron-transporting light-emissive layer and a metal cathode, respectively, showed a maximum luminescence of 25 000 cd/m 2 at 12.5 V.

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confidence: 99%

Synthesis and Properties of Poly[di(1-naphthyl)-4-tolylamine] as a Hole Transport Material

Nomura¹,

Shibasaki²,

Ueda³

et al. 2004

Macromolecules

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“…Especially, the polymeric TAA derivatives exhibit extensive application prospects due to the potential advantages such as possibility of extended -conjugation and excellent film-forming property. The common reactions for the synthesis of poly(triarylamine) (PTAA) where TAA units are linked together in the main chain are Ullman reaction [5], palladium or nickel catalyzed coupling reactions [6], and simple oxidative polymerization using ferric chloride as an oxidizing agent [7,8]. Recently, our group have.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Triarylamine-Based Block Copolymers by Combination of C-N Coupling and ATRP for Photorefractive Applications

Cao¹,

Tsuchiy²,

Shimomura³

et al. 2012

OJOPM

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Poly(4-butyltriarylamine)s with t-butyldimethylsilyl terminal protecting group (PBTPA-TBS) with various molecular weights were prepared by C-N coupling polymerization. The resulting precursors were postfunctionalized and subsequently used as macroinitiators for atom transfer radial polymerization (ATRP) of n-butyl acrylate (n-BA) and ethyl acrylate (EA). Both the polymerization processes were controlled and the polymers were characterized by 1 H NMR, gel permeation chromatography (GPC) and thermal properties, which confirmed the successful synthesis of all the polymers. The microphase separated behaviors of the poly (4-butyltriarylamine)-block-poly (butyl acrylate) (PBTPA-b-PBA) were examined by AFM in the film showing phase separation structures for all the polymers. The photorefractive property of the composite based on PBTPA-b-PBA block copolymer was evaluated by two-beam coupling experiment. A relative high gain coefficient of 42.7 cm −1 was obtained at the electric field of 31 V/m.

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“…The block copolymers containing triphenylamine and perylenediimide as side groups were also prepared [14,15]. Poly(triphenylamine)s (PTPAs) were firstly prepared by oxidative coupling polymerization of triphenylamine derivatives, and it was found that soluble poly(4-butyltriphenylamine) showed high hole mobility and high photoconductivity [38,39]. Recently, we have developed novel synthetic route for the preparation of PTPA utilizing palladium-catalyzed C-N coupling polymerization [40].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Diblock Copolymer Consisting of Poly(4-butyltriphenylamine) and Morphological Control in Photovoltaic Application

et al. 2011

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Abstract:The diblock copolymer PTPA-b-PS consisting of poly(4-butyltripheneylamine) (PTPA) and polystyrene was prepared by atom transfer radical polymerization followed by C-N coupling polymerization. Three types of block copolymers with different contents of polystyrene segment were prepared. The formation of block copolymer was confirmed by 1 H NMR spectra and gel permeation chromatography (GPC) profiles. Time of flight (TOF) measurement revealed that the block copolymer showed higher hole mobility up to 1.3 × 10 −4 cm 2 /Vs compared with PTPA homopolymer. The surface morphology of block copolymer films blended with [6,6]-phenyl-C 61 -butyric acid methyl ester (PCBM) was investigated by Atomic force microscopy (AFM). Introduction of polystyrene segment provided microphase-separated structures with domain sizes of around 20 nm. The photovoltaic device based on PTPA-b-PS, PTPA, and PCBM exhibited higher efficiency than that of homopolymer blend system.

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Oxidative coupling polymerization of 4-methyltriphenylamine

Cited by 72 publications

References 10 publications

Synthesis and Properties of Poly[di(1-naphthyl)-4-tolylamine] as a Hole Transport Material

Synthesis and Properties of Poly[di(1-naphthyl)-4-tolylamine] as a Hole Transport Material

Synthesis and Characterization of Triarylamine-Based Block Copolymers by Combination of C-N Coupling and ATRP for Photorefractive Applications

Synthesis of Diblock Copolymer Consisting of Poly(4-butyltriphenylamine) and Morphological Control in Photovoltaic Application

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