Synthesis and nonlinear optical properties of 1,3- and 1,4-disubstituted type of poly(phenyleneethynylene)s containing electron-donor and acceptor group

Koishi, Katsuya; Ikeda, Tsuyoshi; Kondo, Koichi; Sakaguchi, Toru; Kamada, Kei; Tawa, Keiko; Ohta, Koji

doi:10.1002/(sici)1521-3935(20000301)201:5<525::aid-macp525>3.0.co;2-a

Cited by 15 publications

(10 citation statements)

References 10 publications

(23 reference statements)

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“…The presence of the polarized structure in nonlinear polymers is still sluggish to the point of the increase in χ (3) despite the observation of the enhanced second hyperpolarizability (γ) in donor–acceptor conjugated polymethine dyes 4. Previously, we reported that polyphenylene‐ethynylenes substituted with a donor–acceptor group as the pendants provided only the slight increase in χ (3) 5. In contrast, polydiphenyldiacetylenes can be characterized with the ene‐yne main‐chain structure orthogonal to the stilbene type of side chain that could have the crossover π‐conjugation to the polymer chain.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and nonlinear properties of poly[1,4‐bis(4‐alkylpyridinium)butadiyne triflate]

Iwase

Kondo

Kamada

et al. 2001

J. Polym. Sci. A Polym. Chem.

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1,4‐Bis(4‐alkylpyridinium)butadiyne triflate (2a and 2b) that was prepared by the reaction of 1,4‐bis(4‐pyridyl)butadiyne (1) with alkyl trifluoro‐methanesulfonate, was found to grow into a large crystal as a result of the quaternized structure. The thermal treatment of 2a and 2b gave rise to 1,4‐addition polymerization to yield the polydiacetylene. The third‐order nonlinear optical susceptibility [χ(3)] of the polymer was determined by the femto‐second Z‐scan method to exhibit the remarkable high value of 1.1 × 10−11 esu at 650 nm. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 3686–3691, 2001

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Section: Introductionmentioning

confidence: 99%

Synthesis and nonlinear properties of poly[1,4‐bis(4‐alkylpyridinium)butadiyne triflate]

Iwase

Kondo

Kamada

et al. 2001

J. Polym. Sci. A Polym. Chem.

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“…It was shown that the structural modification of OPEs, especially the substitution of electron withdrawing groups CF 3 and N, could provide an efficient blue light emitter. In earlier studies [9][10][11][12][13], it was reported that the spectral properties (absorption and emission) of oligo-and poly ( p-arylene ethylene)s (OAEs and PAEs) depend on the structure. The structural modification by means of introducing different electron donating and withdrawing groups affect the molecular orbitals of the system, which cause modification to the molecular electronic properties.…”

Section: Introductionmentioning

confidence: 99%

Absorption and emission properties of phenylene ethynylene oligomers: effect of substitution and π-conjugation length

2009

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The optical properties of a series of -conjugated phenylene-ethynylene oligomers (OPEs) have been studied by advanced quantum chemical methods. The ground state and lowest singlet excited state geometries of unsubstituted and different electron donor and acceptor groups substituted OPEs are optimized by density functional theory and configuration interaction singles methods. The absorption and emission spectra of unsubstituted and substituted OPEs have been calculated using the time-dependent density functional theory (TDDFT) method. The results of theoretical calculations are in good agreement with the available experimental results. It has been found that the substitution of electron donating and withdrawing groups in the phenyl ring and conjugation length of the OPEs has significantly affect both the absorption and emission spectra

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“…Pd‐catalyzed polymerization was carried out using standard Schlenk techniques. 4,4′‐Dibromo‐2,3′‐dinitro‐biphenyl,29 3,5‐dibromonitrobenzene,30 and 2,5‐dibromo‐4‐nitroaniline21 were prepared according to the literature. 1,4‐Bis(4,4,5,5‐tetramethyl‐1,3,2‐dioxa‐borolan‐2‐yl)‐2,5‐bis(dodecyloxy)benzene (2) was prepared by the boronation of 1,4‐dibromo‐2,5‐bis(dodecyloxy)benzene (1) with 2‐isopropoxy‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane as described later.…”

Section: Methodsmentioning

confidence: 99%

“…For the nitro‐ p ‐phenylene unit, poly(imide)s,10–12 poly(arylester)s,13–16 poly(arylene‐vinylene)s,17–19 and poly(aryleneethynylene)s20, 21 consisting of the unit have been reported, and polythiophenes22–25 consisting of nitrothiophene have also been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and chemical properties of dielectric polyphenylenes with nitro group

Abe

Tokita

Watanabe

et al. 2008

J of Applied Polymer Sci

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Polyphenylenes consisting of nitrophenylene and didodecyloxy-p-phenylene units have been synthesized by Pd-catalyzed organometallic polycondensation. The polymers showed good solubility and had numberaverage molecular weights (M n ) of 13,000-37,000. Their spin-coated films showed fairly high dielectric constants (e) of 3.75-6.36. The polymers were electrochemically active with electrochemical reduction peaks in the range of À1.72 to À1.99 V versus Ag þ /Ag in an acetonitrile solution of [NEt 4 ]BF 4 (0.10M). The polymer composed of 2,3 0 -dinitrobiphenyl and didodecyloxy-p-phenylene units showed thermotropic liquid crystalline phase at about 240 C. Cast films of the polymer had a birefringent phase at room temperature, suggesting self-assembly of the polymer in the solid. XRD studies revealed that the polymers assumed an ordered structure assisted by aggregation of the long alkoxy side chains in the solid. The polymer main chain in the cast film is considered to be aligned parallel with respect to the surface of substrates.

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Synthesis and nonlinear optical properties of 1,3- and 1,4-disubstituted type of poly(phenyleneethynylene)s containing electron-donor and acceptor group

Cited by 15 publications

References 10 publications

Synthesis and nonlinear properties of poly[1,4‐bis(4‐alkylpyridinium)butadiyne triflate]

Synthesis and nonlinear properties of poly[1,4‐bis(4‐alkylpyridinium)butadiyne triflate]

Absorption and emission properties of phenylene ethynylene oligomers: effect of substitution and π-conjugation length

Synthesis and chemical properties of dielectric polyphenylenes with nitro group

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