Structure and properties of 3-alkoxy substituted polythiophene synthesized at low temperature

Hu, Xiao; Xu, Liguang

doi:10.1016/s0032-3861(00)00299-8

Cited by 89 publications

(80 citation statements)

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“…4 Although the synthesis of alkyl and di-alkoxy substituted polythiophenes has been well established, 5,6 the synthesis of monoalkoxy substituted polythiophenes still remains a problem due to the low molecular weight and poor solubility. [7][8][9][10][11][12][13][14] This paper reports the synthesis and optical properties of three poly(3-alkoxythiophene) derivatives with moderately high molecular weights, which exhibit good solubility and film-forming ability. The introduction of a branched side chain in the monomer increased molecular weight of the polymer.…”

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confidence: 99%

Synthesis and Molecular Weight Dependent Optical Properties of Mono-Alkoxy Substituted Polythiophenes

Zhang

Fujiki

2001

Polym J

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ABSTRACT:Poly(3-alkoxythiophene)s with moderately high molecular weights, which exhibit good solubility and film-forming ability, were successfully synthesized by the nickel (0) coupling reaction in good yields. The introduction of a branched side chain resulted in a molecular weight higher than that of the straight one. Broad photoluminescence (PL), ranging from 579 to 684 nm, was readily obtained by choosing the appropriate molecular weight sample of a mother polymer. This may provide a new method for evaluating organic luminescent materials.KEY WORDS Poly(3-alkoxythiophene) / Nickel Catalyst / Molecular Weight / Optical Properties / π-Conjugating polythiophenes have been considered promising candidates for polymer light-emitting diodes (LEDs), due to the tunability of emission colors, processability, and thermal and chemical stabilities. 1 Emission color closely depends on the extent of the effective conjugation along the backbone, which is mainly controlled by tailoring the structures of the main chain and side chain. 2, 3 Poly(alkoxythiophene)s are known to be useful as hole injection layers to improve the charge transport ability of LEDs, due to higher charge carrier mobility, lower oxidation potential, and better stability in the oxidized state, compared to alkyl substituted polythiophenes. 4 Although the synthesis of alkyl and di-alkoxy substituted polythiophenes has been well established, 5, 6 the synthesis of monoalkoxy substituted polythiophenes still remains a problem due to the low molecular weight and poor solubility. [7][8][9][10][11][12][13][14] This paper reports the synthesis and optical properties of three poly(3-alkoxythiophene) derivatives with moderately high molecular weights, which exhibit good solubility and film-forming ability. The introduction of a branched side chain in the monomer increased molecular weight of the polymer. These results may lead to a facile and inexpensive method for providing variable emission color by choosing the appropriate molecular weight samples of a single mother polymer. EXPERIMENTAL MeasurementsMolecular weights were evaluated by size exclusion chromatography (SEC) on a Shodex KF806 M column (eluent THF, 30 • C) in a Shimadzu liquid chromatography instrument equipped with a photodiode array detector based on the calibration using polystyrene stan- † To whom correspondence should be addressed.dards. Ultraviolet-visible (UV-vis) spectra (room temperature; 21 • C) were recorded on a JASCO V-570 spectrometer. Fluorescence spectra (room temperature; 21 • C) were recorded on a Hitachi F-850 spectrophotometer. NMR spectra were recorded on a Varian Unity 300 spectrometer relative to the TMS internal standard in chloroform-d. Materials3-Methoxythiophene was purchased from Aldrich Chemical Co. (R)-(−)-2-Octanol (≥ 99% e.e. (enantiomeric excess)) was purchased from AZmax Co., Japan. They were used without further purification. Monomer Synthesis3-Alkoxy substituted thiophenes were prepared by transetherification reaction between 3-methoxythiophene and corresponding pr...

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Synthesis and Molecular Weight Dependent Optical Properties of Mono-Alkoxy Substituted Polythiophenes

Zhang

Fujiki

2001

Polym J

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“…Este material tem sido muito estudado devido à presença do oxigênio do grupo alcóxi, que provoca uma diminuição do potencial de oxidação tanto do monômero quanto do polímero, em função do efeito eletrodoador. 93,94 Pesquisadores como Fouad e colaboradores 95 Estudos mostram que estes monômeros têm um baixo potencial de oxidação (devido a sua estrutura conjugada). A polimerização eletroquímica destes monômeros foi realizada através de oxidação anódica, resultando na formação de oligômeros de cadeia curta.…”

Section: Figura 12 Oligômeros Btes Obtidos Por Feng E Colaboradores 75unclassified

“…96,97 Estes copolímeros são obtidos através da mistura de 83 (36), poli(3-tiofeno-β-etanossulfonato) de sódio 84 87 (DPhDTT) (39), poli (3-clorotiofeno) 88 (40), poli(3-clorotiofeno-co-3-metiltiofeno) 88 (41), derivado de politiofeno com uretano substituído na posição β do anel tiofênico 90 (42), poli (3,4-etilenodioxitiofeno) 91 (PEDOT) (43), poli (3-metoxitiofeno) 93 (44), tieno [3,2-b][1]benzotiofeno 95 (TBT) (45) e 6-metoxitieno [3,2- (46) dois ou mais monômeros e, em seguida, realiza-se a polimerização química ou eletroquímica.…”

Section: Figura 12 Oligômeros Btes Obtidos Por Feng E Colaboradores 75unclassified

Oligômeros e polímeros derivados do tiofeno: síntese e aplicações

Alves¹,

Calado²,

Matencio³

et al. 2010

Quím. Nova

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#Thanks a lot, Prof. Hans Viertler, for everything you taught me: a plenty of good chemistry, specially organic chemistry and electrochemistry… Thanks for the good examples to be followed and the mistakes and bad things to be avoided… and finally citing Carl Gustav Jung as followed, thank you for helping me to transform myself in the chemist I am now… " Recebido em 24/3/10; aceito em 27/8/10; publicado na web em 25/10/10 THIOPHENE-BASED OLIGOMERS AND POLYMERS: SYNTHESES AND APPLICATIONS. In this review we summarize recent synthetic investigations about the preparation of oligothiophenes and polythiophenes, the most important π-conjugated organic materials for applications in electrochromic and electroluminescent devices. It is showed that many interesting and novel functionalized oligothiophenes have been synthesized by convenient coupling strategies (Heck, Kumada, Negishi, Suzuki, Stille and Ullmann) and oxidative coupling methods. Synthesis of polythiophenes are also presented and described according to chemical and electrochemical polymerization methodologies. The description of these noteworthy synthetic methods illustrates how important and promising are the interdisciplinary approaches in the obtaining of oligothiophenes and polythiophenes.Keywords: oligomeric and polymeric thiophenes; syntheses; conjugated polymers. INTRODUÇÃOOs polímeros conjugados (PCs) são conhecidos como "metais sintéticos" devido a suas propriedades elétricas, magnéticas, eletrô-nicas e ópticas semelhantes aos dos metais; as propriedades de um polímero convencional (flexibilidade, processabilidade e formação de filmes finos, boa estabilidade térmica, etc.) e as propriedades de um semicondutor combinadas em um único material resultam em polímeros para aplicação no campo da eletrônica orgânica. A incontestável importância científica atual desta classe de materiais pode ser percebida pela concessão do Prêmio Nobel de Química de 2000 para Heeger, McDiarmid e Shirakawa por suas pesquisas com PCs. 1 É digno de nota que, quando estes materiais são estimulados eletricamente, podem ter sua cor variada de forma reversível ou mesmo emitir luz visível, o que possibilita a sua aplicação em diversos dispositivos eletrocrômicos 2 ou diodos emissores de luz orgânicos (OLEDs -Organic Light Emission Diodes). Dentre outras possibilidades de aplicação, pode-se citar o desenvolvimento de condutores elétricos, células fotovoltaicas poliméricas, transistores orgânicos, 3,4 anticorrosivos, 5,6 materiais eletrocrômicos, 7 baterias recarregáveis, 8 etc.Em meio aos diversos PCs pesquisados para o desenvolvimento dos dispositivos eletrônicos orgânicos, tais como politiofenos (1), polipirróis (2), polianilinas (3), 9,10 polifenilenovinilenos (4) 11 (Figura 1), destacam-se os politiofenos e seus derivados, que são os materiais mais estudados nesta área. 2 A possibilidade de aplicação dos politiofenos em dispositivos eletrocrômicos é conhecida desde 1983 12-15 e, em 1986, com a primeira síntese descrita de polialquiltiofenos com processabilidade e projeção a nível...

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“…These curves give a good idea of the glass transition temperature, Tg, of the materials. The glass transition temperature of both P3OT and P3HT is expected to be low (Tg = 50.2°C for P3ATs determined by a Differential Scanning Calorimetry method [20]). We have already shown [21] that the value of Tg have to be higher than the post exposure bake temperature at 115°C of the photolithography process to avoid the occurring of worms-like defects.…”

Section: Thermal Analysismentioning

confidence: 99%

Physical and Optical Properties of Poly(3-AlkylThiophene) with a View to the Fabrication of a Highly Nonlinear Waveguide~!2008-06-17~!2008-08-22~!2008-09-18~!

Messaad¹,

Bosc²,

Haesaert³

et al. 2010

TOMSJ

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Abstract:In order to take advantage of the very high nonlinear susceptibility of conjugated polymer materials, Poly(3-AlkylThiophene)s, P3AT, were synthesized in the laboratory. The physical, thermomechanical and linear optical properties of synthesized P3AT have been investigated and the first experimental attempts at creating nonlinear optical waveguides and determining their characteristics are presented. After synthesizing P3AT, the relationships between polymer chain characteristics and mechanical properties are investigated to see if the polymer is suitable for optical waveguide process technology. We also examine the optical attenuation of the synthesized material, a crucial factor in anticipating the relative opacity of the future component. For the first time we present the absorption spectrum of 3-Octylthiophene molecules in the Near Infra-Red (NIR) region that suggests optical losses for the material are about 0.6 dB.cm -1 at 1550 nm. Next we examined several waveguide structures such as ridge, buried and Strip Loaded WaveGuides (SLWG) based on P3AT material. For the buried waveguides, we have observed the signal transmission and in our opinion the low optical transmission of P3AT ridge and SLWG could be attributed to extrinsic losses (mainly scattering) due to both the remaining insoluble products in the polymer and to the poor adhesion between optical layers.

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Structure and properties of 3-alkoxy substituted polythiophene synthesized at low temperature

Cited by 89 publications

References 33 publications

Synthesis and Molecular Weight Dependent Optical Properties of Mono-Alkoxy Substituted Polythiophenes

Synthesis and Molecular Weight Dependent Optical Properties of Mono-Alkoxy Substituted Polythiophenes

Oligômeros e polímeros derivados do tiofeno: síntese e aplicações

Physical and Optical Properties of Poly(3-AlkylThiophene) with a View to the Fabrication of a Highly Nonlinear Waveguide~!2008-06-17~!2008-08-22~!2008-09-18~!

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