Synthesis and characterization of side-chain poly(methacrylate)s bearing new azo-moieties

Polymer Bulletin

Volumn 65, Issue 9, 2010, Pages 905-916

  Nicolescu, Florica Adriana ^a   Jerca, Valentin Victor ^a   Vuluga, Dumitru Mircea ^a   Vasilescu, Dan Sorin ^b  

^a ACADEMY OF ROMANIAN SCIENTISTS   (Romania)

^b UNIVERSITY POLITEHNICA OF BUCHAREST   (Romania)

Author keywords

Azobenzene; Chromophores; Copolymers; Methyl methacrylate; Reactivity ratios; Side chain moiety

Indexed keywords

ELEMENTAL ANALYSIS; FEED COMPOSITIONS; FREE RADICAL COPOLYMERIZATION; FTIR; GLASS TRANSITION TEMPERATURE; HIGH-CONTENT; INTEGRAL METHOD; METHYL METHACRYLATES; NMR SPECTROSCOPY; POLYMETHACRYLATES; REACTIVITY RATIO; SIDE-CHAIN; SYNTHESIS AND CHARACTERIZATIONS; THERMAL STABILITY;

ACRYLIC MONOMERS; COPOLYMERIZATION; COPOLYMERS; ESTERS; FREE RADICALS; GLASS TRANSITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CHROMOPHORES;

EID: 78649859045     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00289-010-0302-1     Document Type: Article

References (36)

1. Zhao Y, Ikeda T (2009) Smart light-responsive materials; azobenzene-containing polymers and liquid crystals. Wiley, Hoboken
2. Sekkat Z, Knoll W (2002) Photoreactive organic thin films. Academic Press, Amsterdam
3. Kumar GS (1992) Azo functional polymers: functional group approach in macromolecular design. Technomic Publication, Lancaster
4. Durr H, Laurent HB (1990) Photochromism: molecules and systems in studies in organic chemistry, vol 40. Elsevier, Amsterdam
5. Natansohn A, Rochon P, Ho M, Barrett C (1995) Azo polymers for reversible optical storage. 6. Poly[4-(2-methacryloyloxy) ethyl-azobenzene]. Macromolecules 28:4179-4183. doi: 10.1021/ma00116a019
6. S Kawata Y Kawata 2000 Three-dimensional optical data storage using photochromic materials Chem Rev 100 1777 1788 10.1021/cr980073 1:CAS:528:DC%2BD3cXis1GntLg%3D 10.1021/cr980073p
7. A Natansohn P Rochon 2002 Photoinduced motions in azo containing polymers Chem Rev 102 4139 4175 10.1021/cr970155y 1:CAS:528:DC%2BD38XnvV2ktr8%3D 10.1021/cr970155y (Pubitemid 35410368)
8. J Si J Qiu J Zhai Y Shen K Hirao 2002 Photoinduced permanent gratings inside bulk azo dye-doped polymers by the coherent field of a femtosecond laser Appl Phys Lett 80 359 361 10.1063/1.1435808 1:CAS:528:DC%2BD38XlsFemug%3D%3D 10.1063/1.1435808 (Pubitemid 34105348)
9. T Matsui M Ozaki K Yoshino F Kajzar 2002 Fabrication of flexible distributed laser using photoinduced surface relief grating on azo-polymer film as a template Jpn J Appl Phys 12A L1386 L1388 10.1143/JJAP.41.L1386 10.1143/JJAP.41.L1386
10. N Tirelli RA Solaro F Ciardelli S Follonier CH Bosshard P Gunter 2000 Structure-activity relationship of new NLO organic materials based on push-pull azodyes: 4. Side chain polymers Polymer 41 415 421 10.1016/S0032-3861(99)00202-5 1:CAS:528:DyaK1MXntlyitLk%3D 10.1016/S0032-3861(99)00202-5 (Pubitemid 29515507)
11. JP Cresswell MC Petty I Ferguson M Hutchings S Allen TG Ryan CH Wang BS Wherrett 1996 Langmuir-Blodgett deposition and 2nd-order nonlinear optics of several azobenzene dye polymers Adv Mater Optics Electron 6 33 38 10.1002/(SICI)1099-0712(199601)6:1<33::AID-AMO222>3.0.CO;2-5 1:CAS:528:DyaK28XhslCmu7c%3D 10.1002/(SICI)1099-0712(199601)6:1<33::AID- AMO222>3.0.CO;2-5
12. L Angiolini D Caretti L Giorgini E Salatelli 2000 Optically active methacrylic polymers bearing side-chain conjugated azoaromatic chromophores Synth Met 115 235 239 10.1016/S0379-6779(00)00341-6 1:CAS:528: DC%2BD3cXntVCrsL0%3D 10.1016/S0379-6779(00)00341-6
13. KD Singer MG Kuzyk WR Holland JE Sohn J Lalama RB Commizzoli HE Katz ML Schilling 1988 Electro-optic phase modulation and optical second-harmonic generation in corona-poled polymer films Appl Phys Lett 53 1800 10.1063/1.99785 1:CAS:528:DyaL1MXjvFKltw%3D%3D 10.1063/1.99785
14. ATH Koch SV Fridrikh M Warner CE Schwarzwalder SC Moratti RH Friend 1999 Second order nonlinear optical response of nematic liquid crystalline main chain polymers Synth Met 101 244 245 10.1016/S0379-6779(98)01358-7 1:CAS:528:DyaK1MXksF2hs78%3D 10.1016/S0379-6779(98)01358-7
15. KY Sandhya CKS Pillai M Sato N Tsutsumi 2003 Highly stable rigid main-chain nonlinear optical polymers with nematic phase: effect of liquid-crystalline phase on nonlinear optical response J Polym Sci A 41 1527 1535 10.1002/pola.10695 1:CAS:528:DC%2BD3sXjt1Gnu78%3D 10.1002/pola.10695 (Pubitemid 36510859)
16. GA Lindsay JD Stenger-Smith RA Henry JM Hoover RA Nissan KJ Wynne 1992 Main-chain accordion polymers for nonlinear optics Macromolecules 25 6075 10.1021/ma00048a037 1:CAS:528:DyaK38XlvFantbk%3D 10.1021/ma00048a037
17. A Zerroukhi A Trouillet D Blanc B Boinon A Cachard JP Montheard 1994 Syntheses and nonlinear optical properties of polymers prepared from chloromethylstyrene J App Polym Sci 51 1165 1173 10.1002/app.1994.070510702 1:CAS:528:DyaK2cXhvFCjs7k%3D 10.1002/app.1994.070510702
18. AM Albu B Marculescu DS Vasilescu 1999 Synthesis and characterization of some polymers with applications in non-linear optics II; copolymerization of styrene with some monomers containing azo-dyes Eur Polym J 35 2203 2205 10.1016/S0014-3057(99)00019-1 1:CAS:528:DyaK1MXnt1Kis7g%3D 10.1016/S0014- 3057(99)00019-1 (Pubitemid 129662955)
19. Y Sui J Yin Z Hou N Zhu J Lu Y Liu Z Zhu Z Wang 2001 A facile approach to prepare soluble side-chain polyimides for second-order nonlinear optics J Polym Sci A 39 2189 2195 10.1002/pola.1195 10.1002/pola.1195 (Pubitemid 32615882)
20. Z Li Y Zhao J Zhou Y Shen 2000 Synthesis and characterization of two series of polyimides as nonlinear optical materials Eur Polym J 36 2417 2421 10.1016/S0014-3057(00)00033-1 1:CAS:528:DC%2BD3cXls1Clsrw%3D 10.1016/S0014-3057(00)00033-1
21. E Gubbelmans T Verbiest M Van Beylen A Persoons C Samyn 2002 Chromophore-functionalized polyimides with high-poling stabilities of the nonlinear optical effect at elevated temperature Polymer 43 1581 1585 10.1016/S0032-3861(01)00678-4 1:CAS:528:DC%2BD3MXpt1Wqt7s%3D 10.1016/S0032-3861(01)00678-4
22. K Van den Broeck T Verbiest J Degryse M Van Beylen A Persoons C Samyn 2001 High glass transition chromophore functionalized polyimides for second-order nonlinear optical applications Polymer 42 3315 3322 10.1016/S0032-3861(00)00761-8 10.1016/S0032-3861(00)00761-8
23. D Bahuleyan K Sreekumar 1999 Chiral polyesters with azobenzene moieties in the main chain, synthesis and evaluation of nonlinear optical properties J Mater Chem 7 1425 1430 10.1039/a900567f 10.1039/a900567f
24. N Nemoto F Miyata Y Nagase J Abe M Hasegawa Y Shirai 1996 Novel types of polyesters containing second-order nonlinear optically active chromophores with high density Macromolecules 29 2365 2371 10.1021/ma951032n 1:CAS:528: DyaK28XhtlKiurY%3D 10.1021/ma951032n (Pubitemid 126597641)
25. ZS Xu V Drnoyan A Natansohn R Rochon 2000 Novel polyesters with amino-sulfone azobenzene chromophores in the main chain J Polym Sci A 38 2245 2253 10.1002/(SICI)1099-0518(20000615)38:12<2245::AID-POLA130>3.0.CO;2-U 1:CAS:528:DC%2BD3cXjvVSisrw%3D 10.1002/(SICI)1099-0518(20000615)38:12<2245:: AID-POLA130>3.0.CO;2-U
26. H Xie Z Liu X Huang J Guo 2001 Synthesis and non-linear optical properties of four polyurethanes containing different chromophore groups Eur Polym J 37 497 505 10.1016/S0014-3057(00)00146-4 1:CAS:528: DC%2BD3MXivVWhtg%3D%3D 10.1016/S0014-3057(00)00146-4 (Pubitemid 32092135)
27. S Yokoyama T Nakahama A Otomo S Mashiko 2000 Intermolecular coupling enhancement of the molecular hyperpolarizability in multichromophoric dipolar dendrons J Am Chem Soc 122 3174 10.1021/ja993569c 1:CAS:528:DC%2BD3cXhs1Wktbw%3D 10.1021/ja993569c (Pubitemid 30207847)
28. L Najun L Jianmei X Qingfeng X Xuewei W Lihua 2007 Synthesis of optical-active azo-containing acrylates using atom transfer radical polymerization under microwave irradiation Eur Polym J 43 4486 4492 10.1016/j.eurpolymj.2007.04.014 10.1016/j.eurpolymj.2007.04.014 (Pubitemid 47483690)
29. L Najun L Jianmei X Qingfeng X Xuewei W Lihua 2007 Synthesis and third-order NLO properties of polymethacrylates containing pendent azobenzene groups High Perform Polym 19 356 367 10.1177/0954008306074723 10.1177/0954008306074723 (Pubitemid 46809220)
30. L Najun L Jianmei X Xuewei X Qingfeng W Lihua 2009 Synthesis of third-order nonlinear optical polyacrylates containing an azobenzene side chain via atom transfer radical polymerization Dyes Pigments 80 73 79 10.1016/j.dyepig.2008.05.004 10.1016/j.dyepig.2008.05.004
31. AS Rekha D Ratna AB Samui 2007 Synthesis and characterization of azo-based acrylate polymers for use as nonlinear optical materials J App Polym Sci 103 425 431 10.1002/app.24901 1:CAS:528:DC%2BD28Xht1GrtbzE 10.1002/app.24901 (Pubitemid 44832251)
32. K Sadagopan AS Rekha D Ratna AB Samui 2007 Synthesis and characterization of azo-based methacrylate polymers with methoxy and nitro end groups for nonlinear optical applications J App Polym Sci 104 3497 3504 10.1002/app.24656 1:CAS:528:DC%2BD2sXltFChtLc%3D 10.1002/app.24656 (Pubitemid 46787014)
33. FJ Rodriguez C Sanchez B Villacampa R Alcala R Cases M Millaruelo L Oriol 2004 Optical anisotropy and non-linear optical properties of azobenzene methacrylic polymers Polymer 45 2341 2348 10.1016/j.polymer.2004.01.069 1:CAS:528:DC%2BD2cXhs12jtLg%3D 10.1016/j.polymer.2004.01.069 (Pubitemid 38293186)
34. FA Nicolescu VV Jerca C Draghici DM Vuluga DS Vasilescu 2009 Synthesis and characterization of novel azobenzene methacrylate monomers Des Monomers Polymers 12 553 563 10.1163/138577209X12478294517116 1:CAS:528: DC%2BD1MXhsVOhsrfI 10.1163/138577209X12478294517116
35. A Favier M-T Charreyre C Pichot 2004 A detailed kinetic study of the RAFT polymerization of a bi-substituted acrylamide derivative: influence of experimental parameters Polymer 45 8661 8674 10.1016/j.polymer.2004.10.055 1:CAS:528:DC%2BD2cXhtVWgtrjN 10.1016/j.polymer.2004.10.055 (Pubitemid 39550603)
36. Hagiopol C (2000) Copolymerization-toward a systematic approach. Springer, New York