The synthesis, characterization and third-order nonlinear optical character of poly(2,5-dipropargyloxybenzoate) containing a polar aromatic diacetylene

Castañon, Sandra L.; Beristain, Miriam F.; Ortega, Alejandra; Gómez‐Sosa, Gustavo; Muñoz, Eduardo; Pérez-Martínez, Ana Laura; Ogawa, Teiichiro; Halim, M.; Smith, Francis W.; Dorsinville, R.

doi:10.1016/j.dyepig.2010.05.012

Cited by 7 publications

(8 citation statements)

References 19 publications

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“…4-N,N-Bis(hydroxyethyl)aminophenyl-4'-nitrophenylbutadiyne was prepared using the same procedure as previously reported [22] except that the N,N-bis(hydroxyethyl)-4-iodoaniline was prepared employing the method reported by Cross and Davis [23]. The desired chromophore (Scheme 1, I) was isolated by solubility difference and recrystallized from acetone to afford orange crystals in 33% yield and melting at 215 °C (DSC).…”

Section: Diacetylene Preparationmentioning

confidence: 99%

“…When the DA-containing polymers are amorphous, this topochemical polymerization does not occur, but random cross-linking takes place when heated or irradiated giving polymer films with excellent optical quality. [18][19][20][21][22] In this work, a soluble polyisophthalate containing an aromatic DA was synthesized and characterized, and its third-order nonlinear optical susceptibility was determined by the Z-scan technique.…”

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: Diacetylene Preparationmentioning

confidence: 99%

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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“…Besides thermal cross-linking property, highly reactive propargyl ether-terminated monomers can be used in the preparation of diacetylene-containing polymers by means of oxidative coupling chemistry under oxygen atmosphere with copper (I) chloride (CuCl) as the catalyst. [33][34][35][36] These obtained polymers can similarly undergo cross-linked polymerization under ultraviolet irradiation or by annealing at a definite temperature, and they exhibit enhanced mechanical properties and thermostability because of the volume contraction in the covalent coupling of adjacent diacetylene units. [35][36][37][38][39][40] In recent years, several correlative research studies have been reported on the synthesis and characteristics of diacetylene-containing polymers, for example, thermal properties and mechanical strength.…”

Section: Introductionmentioning

confidence: 99%

“…[33][34][35][36] These obtained polymers can similarly undergo cross-linked polymerization under ultraviolet irradiation or by annealing at a definite temperature, and they exhibit enhanced mechanical properties and thermostability because of the volume contraction in the covalent coupling of adjacent diacetylene units. [35][36][37][38][39][40] In recent years, several correlative research studies have been reported on the synthesis and characteristics of diacetylene-containing polymers, for example, thermal properties and mechanical strength. [38][39][40][41] Many of the cured products were characterized by good mechanical and thermal properties and chemical resistance.…”

Section: Introductionmentioning

confidence: 99%

Thermal properties of diacetylene–containing polymer prepared from propargyl-terminated monomer with pyridine

Yang

Jiang

et al. 2016

High Performance Polymers

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A novel diacetylene-containing main chain-type polymer, poly[2,6-bis(4-propargyl-oxy-benzoyl)pyridine] (P 1 ), was synthesized via oxidative coupling reaction with a new propargyl-terminated monomer, 2,6-bis(4-propargyl-oxy-benzoyl)pyridine (M 1 ), which was incorporated a substituted pyridine into the molecular chain of model monomer, 4,4 0 -bis(propargyl-oxy)benzophenone (M 0 ). The structures of the new monomer and the resulting polymer were verified by Fourier transform infrared and proton nuclear magnetic resonance spectroscopies. Differential scanning calorimetry was used to investigate the curing behaviors of M 1 and P 1 . The onset curing temperature of M 1 was 199.0 C, and the exothermic enthalpy of M 1 was 973.4 J g À1 , while the initial curing temperature for polymer P 1 reduced by 48 C and the exothermic enthalpy was almost half. Thermogravimetric analysis (TGA) showed the excellent thermal stabilities of M 1 and its polymer in argon atmosphere (the decomposition temperatures at 5% weight loss were 446 C for M 1 and 370 C for P 1 and their char yields at 800 C exceeded 71%). The above TGA data were superior to that of the model monomer (M 0 ) and its polymer (P 0 ) under the same conditions.

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“…Keywords: alkynes · photochemistry · polymerization · topochemistry · X-ray diffraction tions ranging from biosensors [4c, 15] and nonlinear optics [16] to electron-transport materials. [17] Most of the diacetylene derivatives studied so far contain only one diacetylene fragment, so the conditions of their topochemical polymerization can be fulfilled by a judicious choice of side groups (R 1 and R 2 in Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

A Diacetylene‐Containing Wedge‐Shaped Compound: Synthesis, Morphology, and Photopolymerization

Rosenthal

Hernández

et al. 2013

Chemistry A European J

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A novel wedge-shaped compound containing two diacetylene tails, namely, methyl 3,5-bis(trideca-2,4-diyn-1yloxyl)benzoate (DDABM), was synthesized. As shown by UV/Vis spectroscopy this compound can be polymerized under UV irradiation. The crystalline structure of DDABM was investigated by grazing-incidence wide-angle X-ray diffraction on oriented crystalline films deposited on PTFE-rubbed silicon wafer substrates. Furthermore, the spherulites formed in thicker films were analyzed by wide-angle X-ray diffraction. A molecular packing model of DDABM based on the X-ray diffraction data is proposed. The diacetylene units are oriented along a defined lattice direction with a reticular distance of 4.85 Å, which fulfills the requirements for topochemical polymerization. It was observed that UV polymerization does not affect the phase behavior of the compound, but mainly alters its optical properties.

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The synthesis, characterization and third-order nonlinear optical character of poly(2,5-dipropargyloxybenzoate) containing a polar aromatic diacetylene

Cited by 7 publications

References 19 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

Thermal properties of diacetylene–containing polymer prepared from propargyl-terminated monomer with pyridine

A Diacetylene‐Containing Wedge‐Shaped Compound: Synthesis, Morphology, and Photopolymerization

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