Thermotropic liquid crystalline conjugated polymers, poly(cyclohexylphenoxyacetylenes)-synthesis and properties

Goto, Hiromasa; Akagi, Kazuo; Shirakawa, Ryota; Oh, Sejong; Araya, Kotaro

doi:10.1016/0379-6779(94)03098-q

Cited by 24 publications

(12 citation statements)

References 4 publications

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“…30,31 Materials. Following compounds shown in Scheme 2 were prepared according to methods described in a preceding report 24 with a little modification and the experimental details were described in Supporting Information; 2-(10-bromodecyloxy)tetrahydro-2Hpyran (1), 3-(10-tetrahydro-2H-pyran-2-yloxydecyl)thiophene (2), 3thiophenedecanol (3), 2,5-dibromo-3-thiophenedecanol (4), 4-octylphenylboronic acid (5), 2-Methoxy-6-(4-octylphenyl)naphthalene (6). Other chemicals used in this study were purchased from Kanto Chemical Co., Inc., Tokyo Chemical Industry Co., Ltd., Nacalai Tesque Inc., Sigma-Aldrich Co., LLC., Merck & Co., Inc., or Acros Organics of Thermo Fisher Scientifics, and used without further purification unless stated.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Conjugated polymers bearing a liquid crystalline side-chain have been studied for the purpose of adding specific functionalities of birefringence, self-orientation, and induced anisotropy to semiconducting polymer backbones. − They are prospective candidate of elaborate functional materials as well or better than main-chain type liquid crystalline conjugated polymers, , because their electrical and optical properties are expected to be controlled by the molecular orientation of various liquid crystalline side chains and furthermore macroscopic alignment of them can be progressed by an external perturbation such as shear stress, electric or magnetic field. − …”

Section: Introductionmentioning

confidence: 99%

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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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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Liquid Crystalline Polythiophene Bearing Phenylnaphthalene Side-Chain

et al. 2012

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“…The introduction of orientable pendant mesogenic moieties onto a polyacetylene backbone might increase the conjugation in the main chain and yield polymers with a permanent coupling between electro‐active properties and order. Recently, the use of a rigid polymer backbone, such as a polyene chain, to prepare side‐chain liquid crystalline polymers has been considered with growing interest by various research groups 1–15. Most of the monomers used to this purpose are monosubstituted acetylenes, and their polymerization is generally performed by using Mo, W, or other transition metal‐based catalysts 1–18…”

Section: Introductionmentioning

confidence: 99%

Polyacetylenes Bearing Mesogenic Side Groups: Synthesis and Properties, 2

Stagnaro¹,

Conzatti²,

Costa³

et al. 2003

Macro Chemistry & Physics

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We report on the synthesis of novel liquid crystalline polyacetylenes derived from monosubstituted acetylene monomers. In the monomers A1OBP‐Acn obtained from 3‐bromo‐1‐propyne, the acetylenic moiety is linked through a very short spacer to a biphenyl mesogenic core. Several linear acyl groups of different length are introduced as tail groups. Most of the monomers show liquid crystalline behavior. Polymerizations are carried out in solution with typical metathesis catalysts based on Mo and W and yield polyacetylenes with fairly high molecular weight (MW), soluble in common organic solvents. Polymers PA1OBP‐Acn are fully characterized in terms of molecular structure, by GPC, FT‐IR, NMR and UV/VIS techniques, and of thermal and morphological behavior, by TGA, DSC, POM and X‐ray diffraction experiments. THF solutions of the polymers show a quite relevant photoluminescence with a broadened maximum located around 450 nm.

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“…Here, it is worthwhile to remember that a series of liquid crystalline polyacetylene derivatives prepared with Fe-or Rh-based catalyst and Mo-based catalyst have cis (cis-transoid) and trans (transtransoid) structures in terms of the polyene main chains, respectively. [2][3]8] Since the cis structure is thermally unstable, it is easily isomerized into the trans structure during the first heating process in DSC and polarizing optical microscope measurements. Therefore, the result of Fig.…”

Section: °Cmentioning

confidence: 99%