Synthesis and nonlinear optical properties of novel polyurethanes with high thermal stability of dipole alignment

Lee, Ju‐Yeon; Bang, Han-Bae; Park, Eunju; Baek, Chang Suk; Rhee, Bum Ku; Lee, Seung Mook

doi:10.1016/j.synthmet.2004.02.018

Cited by 30 publications

(13 citation statements)

References 23 publications

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“…The hydroxyl proton of 1a absorbs at d ¼ 4.72 ppm, which disappears in the spectrum of its polymer. A new broad resonance peak, assigned to the urethane proton absorption at d ¼ 9.63 ppm, is emerged on the spectrum of poly(1a) [20,21], further displaying the formation of urethane linkage. All other resonance peaks of the segments of 1a, 1,4-butanediol and 4,4 0 -methylenebis(phenyl isocyanate) appear in the spectrum of poly(1a).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and optical properties of three novel functional polyurethanes bearing nonlinear optical chromophoric pendants with different π electron conjugation bridge structure

Yin

Zhu

et al. 2006

Polymer

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Section: Resultsmentioning

confidence: 99%

Synthesis and optical properties of three novel functional polyurethanes bearing nonlinear optical chromophoric pendants with different π electron conjugation bridge structure

Yin

Zhu

et al. 2006

Polymer

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“…The T g value of polymer 3 measured using DSC is near 102 °C. This T g value is lower than those of the polyurethanes containing dioxynitrostilbene, which are in the range 143–150 °C,, or dioxybenzylidenemalononitrile, which are in the range 135–159 °C , . The TGA and DSC studies show that the decomposition temperature of polymer 3 is higher than the corresponding T g value.…”

Section: Resultsmentioning

confidence: 71%

“…The polymer film exhibits thermal stability up to T g , and no significant SHG decay is observed below 100 °C. This SHG thermal stability is lower than those of polyurethanes containing dioxybenzylidenemalononitrile, which are in the range 145–155 °C,, or dioxynitrostilbene, which are in the range 160–175 °C , . In Fig.…”

Section: Resultsmentioning

confidence: 79%

“…The values of d 31 and d 33 for polymer 3 are 0.69 and 2.06 pm V −1 , respectively. These SHG values are smaller than those of polyurethanes containing 3,4‐dioxynitrostilbene (15.2 pm V −1 ) or 2,4‐dioxybenzylidenemalononitrile (2.35 pm V −1 ), but are larger than those of polyurethanes containing 2,3‐dioxynitrostilbene (1.95 pm V −1 ) . Since the second harmonic wavelength is at 532 nm, which is not in the absorptive region of the resulting polyurethane, there is little resonant contribution to this d 33 value.…”

Section: Resultsmentioning

confidence: 90%

“…Physically crosslinked systems via hydrogen bonds have advantages such as homogeneity and good processability relative to chemically crosslinked systems, which suffer from significant optical loss and poor solubility. Recently we prepared novel polyurethanes containing dioxynitrostilbene, and dioxybenzylidenemalononitrile as NLO chromophores , . The resulting polymers exhibit high thermal stability of second harmonic generation (SHG), which stems from the stabilization of dipole alignment of the NLO chromophore.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and electro‐optic properties of novel polyurethane containing the nitrophenylazoresorcinoxy group

Kim

Song

Jeon

et al. 2012

Polymer International

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A novel Y‐type polyurethane (polyurethane 3) containing 4‐(4‐nitrophenylazo)resorcinoxy groups as nonlinear optical (NLO) chromophores, which constitute part of the polymer backbone, was prepared and characterized. Polyurethane 3 is soluble in common organic solvents such as acetone and N,N‐dimethylformamide. It shows thermal stability up to 270 °C from thermogravimetric analysis with a glass transition temperature obtained from differential scanning calorimetry of 102 °C. The second harmonic generation (SHG) coefficient (d33) of the poled polymer film at 1064 nm fundamental wavelength is 2.06 pm V−1. Polymer 3 exhibits thermal stability up to Tg, and no significant SHG decay is observed below 100 °C, which is acceptable for nonlinear optical device applications. Copyright © 2012 Society of Chemical Industry

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Development of polyurethanes with azo‐type chromophores for second‐order nonlinear optical applications

Tambe

Tasaganva

Jogul³

et al. 2009

J of Applied Polymer Sci

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Active nonlinear optical nitro-substituted thiazole, benzothiazole, and thiadiazole chromophores were prepared and condensed with tolylene-2,4-diisocyanate (TDI) and 4,4 0 -methylenedi(phenyl isocyanate) (MDI) to yield a series of polyurethanes. The resulting polyurethanes were characterized with Fourier transform infrared, proton nuclear magnetic resonance, and ultraviolet-visible spectroscopy, differential scanning calorimetry, thermogravimetric analysis, and gel permeation chromatography. The weight-average molecular weights of the polyurethanes ranged between 19,500 and 28,000 (weight-average molecular weight/number-average molecular weight ¼ 1.71-2.15). All the polyurethanes exhibited excellent solubility in most common organic solvents, and this indicated that these polyurethanes offered good processability. The glass-transition temperatures (T g 's) of the polyurethanes were in the range of C. Among the polyurethanes, chromophores containing the nitrothiazole moiety exhibited lower T g values in comparison with those of chromophores containing nitrobenzothiazole and nitrothiadiazole moieties. This was attributed to the small size of the nitrothiazole moiety in the polyurethane matrix. The polyurethanes containing a TDI backbone demonstrated relatively high T g values in comparison with those of the polyurethanes containing an MDI backbone. This was a result of an enhancement of the rigidity caused by the incorporation of a toluene ring into the polyurethane backbone. The second harmonic generation (SHG) coefficients of the poled polyurethane films ranged from 67.29 to 105.45 pm/V at 1064 nm. High thermal endurance of the poled dipoles was observed for all the polyurethanes. This was attributed to the formation of extensive hydrogen bonds between urethane linkages. Furthermore, none of the developed polyurethanes showed SHG decay below 150 C, and this signified their acceptability for nonlinear optical devices.

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Synthesis and nonlinear optical properties of novel polyurethanes with high thermal stability of dipole alignment

Cited by 30 publications

References 23 publications

Synthesis and optical properties of three novel functional polyurethanes bearing nonlinear optical chromophoric pendants with different π electron conjugation bridge structure

Synthesis and optical properties of three novel functional polyurethanes bearing nonlinear optical chromophoric pendants with different π electron conjugation bridge structure

Synthesis and electro‐optic properties of novel polyurethane containing the nitrophenylazoresorcinoxy group

Development of polyurethanes with azo‐type chromophores for second‐order nonlinear optical applications

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