Polymerization of Diphenylbutadiyne by Gamma Rays Irradiation in the Molten State

Beristain, Miriam F.; Ogawa, Teiichiro; Gómez‐Sosa, Gustavo; Muñoz, Eduardo; Maekawa, Yasunari; Halim, Faisal; Smith, Francis W.; Dorsinville, R.

doi:10.1080/15421401003716130

Cited by 12 publications

(14 citation statements)

References 12 publications

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“…The eSR spectra confirmed the presence of stable radicals polymerization. [15] The polymer had a glass transition temperature, T g , around 115 °C, which was in accordance with its dimensional change observed in the thermomechanical analysis. The large exothermic peak is due to the thermal oligomerization of DA groups.…”

Section: Morphology and Thermal Propertiessupporting

confidence: 82%

“…Moltenstate polymerization of diphenylbutadiyne with gamma irradiation above its melting point has been reported obtaining amorphous oligomers soluble in solvents. [15] There is an alternative choice for obtaining PDA films by their preparation from soluble polymers containing DA groups either in their main chains or side chains, followed by their polymerization to develop PDA network in the films. In the case, when the DA groups are aligned in polymer crystallites in the manner that topochemical polymerization takes place, films containing PDA network are obtained.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of a diacetylene-containing polyisophthalate and its third-order nonlinear optical susceptibility

Beristain

Ortega

Gómez‐Sosa

et al. 2016

Designed Monomers and Polymers

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a Centro de nanociencias y nanotecnología, Universidad nacional autónoma de Mexico, ensenada, México; b instituto de investigaciones en Materiales, Universidad nacional autónoma de México, Mexico, México; c electrical engineering Department, City College of new york, new york, Usa ABSTRACTIn order to obtain amorphous thin films of a polydiacetylene, a polyisophthalate containing a push-pull diacetylene chromophore was synthesized by the reaction of p-(N,N-diethanolamino)p'-nitrodiphenylbutadiyne with isophthaloyl chloride in anhydrous 1-methyl-2-pyrrolidone. The polymer was soluble in organic solvents, such as chloroform, tetrahydrofuran, dimethylformamide, etc., and films with good optical quality were obtained by spin coating from its N-methyl-2pyrrolidone solution. It was characterized by 1 H-NMR, IR, DSC, UV-Visible, X-ray, etc. The diacetylene groups underwent polymerization in the film when irradiated with UV light at 120 °C under Ar atmosphere, and it contained free radicals with a radical concentration of 10 16 radicals/g. The thirdorder nonlinear optical susceptibility, χ (3) , of the polymer film measured by the Z-scan technique at 1064 nm was not noticeable, but when the film was heated and irradiated with UV light, a χ (3) value of 6.4 × 10 −10 esu was obtained due to increase in π-conjugation by the formation of polydiacetylene in the side chain.

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Section: Morphology and Thermal Propertiessupporting

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Synthesis of a diacetylene-containing polyisophthalate and its third-order nonlinear optical susceptibility

Beristain

Ortega

Gómez‐Sosa

et al. 2016

Designed Monomers and Polymers

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“…Diphenyl butadiynes have emerged as one of the important candidates among alkynyl derivatives in both experimental and theoretical research. While the butadiynyl derivatives have found applications in liquid crystals, [1][2][3][4] molecular rotors, 5 supramolecular stabilization 6 and anti-viral properties; 7 their structural, vibrational and electronic properties [8][9][10][11][12][13][14] have also gained considerable interest. The butadiynyl derivatives are also found to be effective fluorescent probes leading to the development of fluorescent anion sensors.…”

Section: Introductionmentioning

confidence: 99%

Substituted diphenyl butadiynes: a computational study of geometries and electronic transitions using DFT/TD-DFT

Pati

Gharpure

Mishra

2014

Phys. Chem. Chem. Phys.

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This work is aimed at theoretical understanding of electronic absorption and emission energies of a series of substituted diphenyl butadiynes through an assessment of several TDDFT functionals and a detailed study of solvent effects on their ground and excited state structures and properties. Out of a series of functionals examined, the coulomb attenuated DFT functional CAM-B3LYP is found to be most successful in predicting charge transfer absorption and emission energies of such derivatives. However, TDDFT potential energy surfaces obtained from hybrid functionals such as B3LYP and PBE0 are found to give a good description of the stability of locally excited (LE) and intramolecular charge transfer (ICT) states as a function of torsional angle, for the butadiynyl fluorophores. Interesting structural variations are observed in the ground and excited state optimized geometries of the fluorophores. The ICT emission of the butadiynyl fluorophores is observed to originate from the twisted state where the two phenyl rings in the diphenyl butadiyne get twisted around the butadiyne moiety. A bending of the butadiyne moiety is noted for some of the butadiynyl derivatives in the ICT emissive state. In addition, the direction of absorption and emission transition dipole moment vectors of the butadiynyl fluorophores is found to depend on the nature of substituents present at the periphery of the diphenyl butadiyne moiety.

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“…The g-irradiation or UV irradiation in the presence of BME can induce a free radical reaction in sequence which allows for a cascade reaction to occur throughout the distinct hydrophobic domains of the mesophases and aromatic diacetylenes were found to form stable diradicals which in turn produce oligomers. [9][10][11][12][13] The birefringence before and after irradiation revealed an anisotropic structure, which was confirmed by polarized light microscopy ( Fig. 1 and see ESI, † Fig.…”

Section: Resultsmentioning

confidence: 58%

“…6,7 The synthesis of poly(diphenylbutadiyne) (PDPB) usually occurs by closely packed pre-organization of the monomer, 1,4-diphenylbutadiyne (DPB), by photo-mediated or radiation-induced polymerization leading to extremely linear, aligned polymerized domains of 1,4-disubstituted polydiacetylenes. 8,9 In general, unless conjugated polymers are molecularly and macroscopically assembled and aligned with a well-defined structure, their superior optoelectronic properties for device application cannot be fully realized. But the majority of these polymers are extremely brittle and difficult to process due to their conjugated backbone.…”

Section: Introductionmentioning

confidence: 99%

Conducting polymer nanofibers with controlled diameters synthesized in hexagonal mesophases

et al. 2015

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Polymerization of Diphenylbutadiyne by Gamma Rays Irradiation in the Molten State

Cited by 12 publications

References 12 publications

Synthesis of a diacetylene-containing polyisophthalate and its third-order nonlinear optical susceptibility

Synthesis of a diacetylene-containing polyisophthalate and its third-order nonlinear optical susceptibility

Substituted diphenyl butadiynes: a computational study of geometries and electronic transitions using DFT/TD-DFT

Conducting polymer nanofibers with controlled diameters synthesized in hexagonal mesophases

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