Synthesis and properties of liquid crystaline polythiophene derivatives

Osaka, Itaru; Shibata, Shotaro; Toyoshima, R.; Akagi, Kazuo; Shirakawa, Hideki

doi:10.1016/s0379-6779(98)01202-8

Cited by 27 publications

(4 citation statements)

References 8 publications

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“…Particularly, LC polythiophene derivative is one of the most intriguing polymers, because its electrical and optical properties are expected to be controlled using molecular orientation of the LC side chain. A variety of polythiophenes containing liquid-crystalline mesogens and lightemitting chromophores have been prepared [27][28][29][30][31][32][33][34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Light-Emitting Polythiophene Derivatives Bearing Terphenyl Mesogenic Pendant

Chen

Zhou

et al. 2010

Molecular Crystals and Liquid Crystals

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A series of polythiophenes containing terphenyl mesogenic side chain at the third position through ester bonding was synthesized by dehalogenative polycondensation. The thiophene monomers 2,5-bromo-3-{[(4-(4 0 -cyano)terphenyloxy)carbonyl]-methyl]}-thiophene [M(CN)] and 2,5-bromo-3-{[(4-(4 0 -methoxy)terphenyloxy)-carbonyl]methyl}-thiophene [M(OCH 3 )] were prepared via Suzuki reation and esterification reactions, in sequence. The structures and properties of the monomers and polymers were characterized and evaluated with nuclear magnetic resonance, infrared spectroscopy, thermogravimetry, differential scanning calorimetry, polarized optical microscopy, ultraviolet spectroscopy, and photoluminescence. All of the polymers were stable, losing little of their weights when heated to !300 C. The polymers showed good solubility and could be dissolved in common solvents such as CHCl 3 , THF, DMF, etc. The monomers exhibited enantiotropic SmA d phases with a bilayer arrangement in the heating and cooling processes. Due to short spacer methylene ester between the bulk terphenyl mesogenic side chain and rigid polythiophene main chain, the polymers could not exhibit liquid crystallinty at elevated temperature. The existence of the chromophoric terphenyl core endows the polymers with high photoluminescence. When their CH 2 Cl 2 solutions were photoexcited, the polymers emitted a strong UV light about 400 nm.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Light-Emitting Polythiophene Derivatives Bearing Terphenyl Mesogenic Pendant

Chen

Zhou

et al. 2010

Molecular Crystals and Liquid Crystals

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“…Other groups have also performed research in this area, e.g., Shirakawa et al who achieved orientation of a LC polythiophene through a rubbing treatment at LC temperature. Thus they obtained macroscopically aligned films [7]. The synthesis of 4-cyano-4'- [8-(3-thienyl)octyloxy]biphenyl, its LC behaviour, and the electrochemical polymerization to the respective polythiophene derivative was reported by Roncali et al The conductivity was stated to be between 0.01 and 0.1 S/cm [8].…”

Section: Introductionmentioning

confidence: 94%

Annealing effects on the electrical conductivity of polymerized liquid crystalline 3,4-ethylenedioxythiophene derivatives

Wrubbel¹,

Ritter²,

Reuter

et al. 2006

E-Polymers

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3,4-Ethylenedioxythiophene derivatives with aromatic, in most cases mesogenic, side groups were synthesized and their liquid crystal behaviour was characterized. These monomers were polymerized oxidatively to charged, electrically conductive polythiophenes. X-ray and atomic force microscopy studies were performed. Films of theses polythiophenes achieved via in situ polymerization were prone to a significant increase of the conductivity by annealing.

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“…Polythiophene derivatives have been drawing much attention for their wide-spreading potential of applications, such as organic light emitting diodes, − polymer solar cells, − and organic field effect transistors. , Therefore, they have also been investigated as π-conjugated backbone of the side-chain type polymer liquid crystals. For development of liquid crystallinity of polythiophenes, selective 2,5-polymerization of thiophene having mesogenic group at 3-position was crucial and several methods have successfully produced characteristic liquid crystalline polythiophenes, respectively. ,,− However, the excellent liquid crystalline polythiophenes, in which a fair percentage of insulating parts occupied, have faced a dilemma of sacrificing inherent electrical and optical properties of polythiophene. Replacement of the insulating side chains by semiconducting ones might be a solution and development strategy.…”

Section: Introductionmentioning

confidence: 99%

Liquid Crystalline Polythiophene Bearing Phenylnaphthalene Side-Chain

et al. 2012

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Polythiophene bearing a 2-phenylnaphthalene side group at 3-position was synthesized from a 2,5dibromothiophene monomer by two polymerization methods, i.e., Yamamoto dehalogenative polycondensation using Ni(cod) 2 and Ni-catalyzed chain-growth polymerization. Polymers prepared by the former method had good solubility for organic solvents, 6300−8400 g mol −1 of number-average molecular weights, absorption bands at around 300 and 385 nm due to π−π* transitions at the phenylnaphthalene moiety and polythiophene backbone, a main fluorescence emission band at around 540 nm from the polythiophene backbone in solution and film state, and presence of enantiotropic liquid crystalline phases which enabled to construct an arrayed state. On the other hand, the latter polymer showed considerably red-shifted absorption and emission bands at around 444 and 585 nm in solution and 509 and 720 nm in film state respectively, but had poor solubility and unresolved mesophases.

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Synthesis and properties of liquid crystaline polythiophene derivatives

Cited by 27 publications

References 8 publications

Synthesis and Properties of Light-Emitting Polythiophene Derivatives Bearing Terphenyl Mesogenic Pendant

Synthesis and Properties of Light-Emitting Polythiophene Derivatives Bearing Terphenyl Mesogenic Pendant

Annealing effects on the electrical conductivity of polymerized liquid crystalline 3,4-ethylenedioxythiophene derivatives

Liquid Crystalline Polythiophene Bearing Phenylnaphthalene Side-Chain

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