Photoresponsive behavior of methyl methacrylate/trans-4-stilbene methacrylate statistical copolymers in solution and the solid state

Tsai, Fu Jya; Torkelson, John M.; Lewis, Frederick D.; Holman, Bruce

doi:10.1021/ma00207a041

Cited by 9 publications

(8 citation statements)

References 13 publications

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“….3 (ArH),4.55 (ArCH2C1), 3.8 (OCH3),3.55 (OCH3), 2.95 (OCH3),1.6 (CH3),0.5-2.3 (backbone CH andCH2); Tg = 111°C.Synthesis of Poly[methylrnethacrylate-co-(diethyl vinyl benzylphosphonate)]To a refluxing solution of 25.0 g poly[methylmethacrylate-co-(vinylbenzyl chloride)] and 400 mL bis(2-ethoxyethyl) ether was slowly added a solution of 100 mL triethylphosphite and 100 mL bis(2ethoxyethyl) ether, over 3 h. The reaction mixture was refluxed an additional 24 h, then cooled to room temperature,and the polymer was precipitated with hexane. The white solid polymer was further purified by dissolution in acetone and reprecipitation with hexane.…”

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confidence: 99%

Modified horner–emmons reaction of polymeric phosphonates: Versatile synthesis of pendant stilbene‐containing polymers

Belfield

Wang

1995

J. Polym. Sci. A Polym. Chem.

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SYNOPSISPoly[styrene-co-(diethyl vinylbenzylphosphonate)] and poly[methylmethacrylate-co-(diethyl vinylbenzylphosphonate)] were prepared and used in modified Horner-Emmons reactions to synthesize polymers with covalently attached stilbene groups. This versatile new method allowed for the preparation of polymers with either electron-donor (OCH3, CH3) or electron-acceptor (Br, NOz) substituents on the stilbene aromatic ring. The resulting polymers were characterized by 'H NMR, FT-IR, UV-visible, DSC, and size exclusion chromatography. Efficient transformation of polymeric pbosphonates to the polymeric stilbene derivatives was realized. Size exclusion chromatographic analyses demonstrated that the reaction conditions have no deleterious effect on the molecular weight distribution of the various polymers that were prepared. Photochromic behavior was demonstrated for one of the derivatives. 0

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confidence: 99%

Modified horner–emmons reaction of polymeric phosphonates: Versatile synthesis of pendant stilbene‐containing polymers

Belfield

Wang

1995

J. Polym. Sci. A Polym. Chem.

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“…Stilbene and its derivatives are known to undergo several photochemical reactions when irradiated with ultraviolet light . In a previous study it was shown that a copolymer containing MAES shows photoisomerization when irradiated with ultraviolet light . In this study we report on an exclusive photodimerization when thin films of PMAES and PMADMES were irradiated with ultraviolet light from a frequency tripled Nd:YAG laser (355 nm).…”

Section: Resultsmentioning

confidence: 74%

“…To ensure the decrease in absorbance is due to photodimerization and not due to photoisomerization, like it was reported in a previous study, we analyzed the photoreaction in the polymer with several complementary methods. In the case that E/Z -isomerization would be contributing to the overall changes observed, phenanthrene formation should be detectable, caused by oxidation through air.…”

Section: Resultsmentioning

confidence: 99%

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Selective [2 + 2]-Cycloaddition in Methacrylic Stilbene Polymers without Interference from E/Z-Isomerization

2011

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Stilbene is known to undergo two different reactions upon photochemical excitation. The first is an E/Z isomerization and the second is a [2 + 2]-cycloaddition of two stilbene molecules. Because both reactions occur in parallel their use is limited. Here we report on photorefractive polymers with a methacrylate backbone and covalently attached 4-hydroxy-(E)-stilbene or 3,5-dimethoxy-4-hydroxy-(E)-stilbene units in the side chain which show [2 + 2]-cycloaddition only. Both polymers, poly(4-methacryloyloxy-(E)-stilbene) (PMAES) and poly(4-methacryloyloxy-3,5-dimethoxy-(E)-stilbene) (PMADMES), show very high initial refractive indices of 1.6533 for PMAES and 1.6288 for PMADMES. The photochemical reaction upon laser irradiation with 355 nm was monitored by UV/vis, fluorescence, and IR spectroscopy. The light-induced changes of the refractive index at 633 nm measured by surface plasmon resonance (SPR) were found to be Δn > 0.05 for PMAES and Δn > 0.04 for PMADMES. The sensitivity of PMADMES is enhanced compared to PMAES due to the electron donating groups (EDG) as the direct comparison of both polymers shows. Both polymers are useful for optical devices because they do not show any absorption in the visible range and are noncrystalline as determined by wide-angle X-ray scattering (WAXS) and differential scanning calorimetry (DSC).

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“…17,18 Trans-4-hydroxystilbene A 1-l round-bottomed flask was charged with a mixture of 4-hydroxybenzaldehyde (122 g, 1 mol), phenylacetic acid (184 g, 1.35 mol) and piperidine (400 ml), and the mixture was refluxed for 6 h. The mixture was then cooled and poured onto crushed ice. The mixture was acidified to pH E5 with concentrated hydrochloric acid diluted to 1:6 (v/v) with water to dissolve the piperidine, and the suspended product was intensively stirred to break up larger particles.…”

Section: Experimental Procedures Preparation Of Tsma Monomermentioning

confidence: 99%

Design and synthesis of a zero-photoelastic birefringence polymer with a high glass-transition temperature by a random copolymerization method

Shafiee

Tagaya

Koike

2011

Polym J

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We designed and synthesized a zero-photoelastic birefringence polymer that had a high glass-transition temperature (T g ) by introducing trans-stilbene units into the side chains of the copolymer by a random copolymerization method. The concentration of the trans-stilbene units required to compensate for photoelastic birefringence in the random copolymer was lower than that required in a polymer prepared by an anisotropic molecule dopant method, because the presence of an anisotropic moiety in the side chain of the polymer has a greater effect than an anisotropic molecule doped in the polymer. Furthermore, the polymer with trans-stilbene units in side chains showed a higher T g than the polymer containing an anisotropic dopant. We conclude that the introduction of an anisotropic molecule of a similar or larger size to trans-stilbene into the side chain gives a polymer with a high T g .

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Photoresponsive behavior of methyl methacrylate/trans-4-stilbene methacrylate statistical copolymers in solution and the solid state

Cited by 9 publications

References 13 publications

Modified horner–emmons reaction of polymeric phosphonates: Versatile synthesis of pendant stilbene‐containing polymers

Modified horner–emmons reaction of polymeric phosphonates: Versatile synthesis of pendant stilbene‐containing polymers

Selective [2 + 2]-Cycloaddition in Methacrylic Stilbene Polymers without Interference from E/Z-Isomerization

Design and synthesis of a zero-photoelastic birefringence polymer with a high glass-transition temperature by a random copolymerization method

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