Blue-luminescent poly(p-phenylenevinylene) derivatives: Synthesis and effect of side-group size on the optical properties

European Polymer Journal

Volumn 47, Issue 1, 2011, Pages 78-87

  Jaballah, Nejmeddine ^a   Chemli, Mejed ^a   Hriz, Khaled ^a   Fave, Jean Louis ^b   Jouini, Mohamed ^c   Majdoub, Mustapha ^a  

^a FACULTÉ DES SCIENCES DE MONASTIR   (Tunisia)

^b INSTITUT DES NANOSCIENCES DE PARIS   (France)

^c UNIVERSITÉ PARIS DIDEROT   (France)

Author keywords

Bisphenol A; Blue luminescence; Conjugated polymers; Poly(p phenylenevinylene); Semi conducting polymers; Side group effect

Indexed keywords

BAND GAPS; BISPHENOL A; BLUE EMISSION; BLUE LUMINESCENCE; DILUTE SOLUTION; FLUORESCENCE SPECTRA; FTIR SPECTROSCOPY; GREEN FLUORESCENCE; GROUP SIZE; OPTICAL BEHAVIOR; POLY(P-PHENYLENE VINYLENE) DERIVATIVES; POLY(P-PHENYLENEVINYLENE); SIDE-GROUP EFFECT; SINGLE LAYER; THIN SOLID FILM; TURN ON VOLTAGE; UV-VIS ABSORPTIONS;

ABSORPTION SPECTROSCOPY; CHROMOPHORES; CONDUCTING POLYMERS; CONJUGATED POLYMERS; CYCLIC VOLTAMMETRY; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MATERIALS PROPERTIES; OPTICAL PROPERTIES; ORGANIC CONDUCTORS; ORGANIC SOLVENTS; PHENOLS; POLYCONDENSATION; POLYMER FILMS; SPONTANEOUS EMISSION; TIN; TIN OXIDES;

ORGANIC POLYMERS;

EID: 78649630289     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2010.10.017     Document Type: Article

References (42)

1. J.H. Burroughes, D.D.C. Bradley, A.R. Brown, R.N. Marks, K. Mackay, and R.H. Friend Light-emitting diodes based on conjugated polymers Nature 347 1990 539 541
2. A. Kraft, A.C. Grimsdale, and A.B. Holmes Electroluminescent conjugated polymers - seeing polymers in a new light Angew Chem Int Ed Engl 37 1998 402 428
3. L. Akcelrud Electroluminescent polymers Prog Polym Sci 28 2003 875 962
4. J.L. Segura The chemistry of electroluminescent organic materials Acta Polym 49 1998 319 344
5. D. Xiang, Q. Shen, S. Zhang, and X. Jiang Synthesis and characterization of novel soluble alternating copoly(phenylene vinylene) derivative for light-emitting electrochemical cell J Appl Polym Sci 88 2003 1350 1356
6. Q. Sun, C. Yang, H. Wang, G. He, and Y. Li Polymer light-emitting electrochemical cell based on a block copolymer containing tri(ethyleneoxide) spacers Polym Adv Technol 13 2002 663 669
7. A.R. Murphy, and J.M.J. Fréchet Organic semiconducting oligomers for use in thin film transistors Chem Rev 107 2007 1066 1096
8. S. Gunes, H. Neugebauer, and N.S. Sariciftci Conjugated polymer-based organic solar cells Chem Rev 107 2007 1324 1338 (Pubitemid 46736541)
9. J.L. Segura, N. Martin, and D.M. Guldi Materials for organic solar cells: the C60/π-conjugated oligomer approach Chem Soc Rev 34 2005 31 47
10. S.W. Thomas III, G.D. Joly, and T.M. Swager Chemical sensors based on amplifying fluorescent conjugated polymers Chem Rev 107 2007 1339 1386
11. U. Lange, N.V. Roznyatovskaya, and V.M. Mirsky Conducting polymers in chemical sensors and arrays Anal Chim Acta 614 2008 1 26
12. D.Y. Kim, H.N. Cho, and C.Y. Kim Blue light emitting polymers Prog Polym Sci 25 2000 1089 1139
13. Y. Ohmori, K. Uchida, K. Muro, and K. Yoshino Blue electroluminescent diodes utilizing poly(alkylfluorene) Jpn J Appl Phys 30 1991 1941 1943
14. J.H. Lee, and D.H. Hwang Alkoxyphenyl-substituted polyfluorene: a stable blue-light-emitting polymer with good solution processability Chem Commun 22 2003 2836 2837
15. A. Edwards, S. Blumstengel, I. Sokolik, R. Dorsinville, H. Yun, and T.K. Kwei Blue photo- and electroluminescence from poly(benzoyl-1,4-phenylene) Appl Phys Lett 70 1997 298 300
16. M.R. Andersson, M. Berggren, G. Gustafsson, T. Hjertberg, O. Inganäs, and O. Wennerström Synthesis of poly(alkylthiophenes) for light-emitting diodes Synth Met 71 1995 2183 2184
17. L. Liao, Y. Pang, L. Ding, and F.E. Karasz Blue-emitting soluble poly(m-phenylenevinylene) derivatives Macromolecules 34 2001 7300 7305
18. A.R. Brown, P.L. Burn, D.D.C. Bradley, R.H. Friend, A. Kraft, and A.B. Holmes Blue-shifted electroluminescence from a stable precursor to poly(p-phenylene vinylene) Mol Cryst Liq Cryst 216 1992 111 116
19. R. Gowri, D. Mandal, B. Shivkumar, and S. Ramakrishnan Synthesis of novel poly[(2,5-dimethoxy-p-phenylene)vinylene] precursors having two eliminatable groups: an approach for the control of conjugation length Macromolecules 31 1998 1819 1826
20. M. Hay, and F.L. Klavetter Aliphatic phenylene vinylene copolymers: tuning the color of luminescence through co-monomer feed ratios J Am Chem Soc 117 1995 7112 7118
21. Z. Yang, I. Sokolik, and F.E. Karasz A soluble blue-light-emitting polymer Macromolecules 26 1993 1188 1190
22. C.Y. Liau, Y.Y. Gan, Y. Zhou, Y.L. Lam, and L.H. Gan Studies of an intrinsically soluble copolymer with well-defined alternating substituted p-phenylenevinylene and hexanedioxy blocks Polymer 41 2000 7339 7346
23. L.J. Rothberg, M. Yan, F. Papadimitrakopoulos, M.E. Galvin, E.W. Kwock, and T.M. Miller Photophysics of phenylenevinylene polymers Synth Met 80 1996 41 58
24. N. Jaballah, H. Trad, M. Majdoub, M. Jouini, J. Roussel, and J.L. Fave Synthesis and characterization of new blue-photoluminescent copolymer derived from bisphenol A J Appl Polym Sci 99 2006 2997 3004
25. H. Trad, M. Majdoub, and J. Davenas Soluble PPVs with few structural defects: synthesis and characterization Mater Sci Eng C 26 2006 334 339
26. N. Jaballah, M. Majdoub, J.L. Fave, C. Barthou, M. Jouini, and J. Tanguy New confined p-phenylenevinylene (PPV)-type polymer analogue of poly(phenylene sulfide) Eur Polym J 44 2008 2886 2892
27. F. Wang, F. He, Z. Xie, M. Li, M. Hanif, and X. Gu A solution-processible poly(p-phenylene vinylene) without alkyl substitution: introducing the cis-vinylene segments in polymer chain for improved solubility, blue emission, and high efficiency J Polym Sci, Part A: Polym Chem 46 2008 5242 5250
28. H. Ndayikengurukiye, S. Jacobs, W. Tachelet, J. Van Der Looy, A. Pollaris, and H.J. Geise Alkoxylated p-phenylenevinylene oligomers: synthesis and spectroscopic and electrochemical properties Tetrahedron 53 1997 13811 13828
29. F. Wang, F. He, Z.Q. Xie, Y.P. Li, M. Hanif, and M. Li Poly(p-phenylene vinylene) derivatives with different contents of cis-olefins and their effect on the optical properties Macromol Chem Phys 209 2008 1381 1388
30. L. Liao, L. Ding, F.E. Karasz, and Y. Pang Poly[(2-alkoxy-5-methyl-1,3- phenylene vinylene)-alt-(phenylene vinylene)] derivatives with different contents of cis- and trans-olefins: the effect of the olefin bond geometry and conjugation length on luminescence J Polym Sci, Part A: Polym Chem 42 2004 303 316
31. Y. Ichino, J.P. Ni, Y. Ueda, and D.K. Wang Vibronic structures in the optical spectra of distyrylbenzene derivatives Synth Met 116 2001 223 227
32. F.Z. Henari, H. Manaa, K.P. Kretsch, W.J. Blau, H. Rost, and S. Pfeiffer Effective stimulated emission and excited state absorption measurements in the phenylene-vinylene oligomer (1,4-bis-(alpha-cyanostyryl)-2,5-dimethoxybenzene) Chem Phys Lett 307 1999 163 166
33. C. Ton-That, G. Stockton, M.R. Phillips, T.P. Nguyen, C.H. Huang, and A. Cojocaru Luminescence properties of poly (phenylene vinylene) derivatives Polym Int 57 2008 496 501
34. L. Feng, and Z. Chen Synthesis and photoluminescent properties of polymer containing perylene and fluorene units Polymer 46 2005 3952 3956 (Pubitemid 40554349)
35. B. Fan, Q. Sun, N. Song, H. Wang, H. Fan, and Y. Li Electroluminescent properties of a partially-conjugated hyperbranched poly(p-phenylene vinylene) Polym Adv Technol 17 2006 145 149
36. Y. Shirota, and H. Kageyama Charge carrier transporting molecular materials and their applications in devices Chem Rev 107 2007 953 1010
37. M. Cheng, Y. Xiao, W.L. Yu, Z.K. Chen, Y.H. Lai, and W. Huang Synthesis and characterization of a cyano-substituted electroluminescent polymer with well-defined conjugation length Thin Solid Films 363 2000 110 113
38. J.L. Bredas, R. Silbey, D.S. Bordeaux, and R.R. Chance Chain-length dependence of electronic and electrochemical properties of conjugated systems: polyacetylene, polyphenylene, polythiophene, and polypyrrole J Am Chem Soc 105 1983 6555 6559
39. F. Wu, W. Tian, J. Sun, J. Shen, X. Pan, and Z. Su Study on the electronic structure of phenylene vinylene dimers with different substituents Mater Sci Eng B 85 2001 165 168
40. D.A.M. Egbe, B. Carbonnier, E.L. Paul, D. Muhlbacher, T. Kietzke, and E. Birckner Diyne-containing PPVs: solid-state properties and comparison of their photophysical and electrochemical properties with those of their yne-containing counterparts Macromolecules 38 2005 6269 6275
41. D.R.T. Zahn, G.N. Gavrila, and G. Salvan Electronic and vibrational spectroscopies applied to organic/inorganic interfaces Chem Rev 107 2007 1161 1232
42. P.I. Djurovich, E.I. Mayo, S.R. Forrest, and M.E. Thompson Measurement of the lowest unoccupied molecular orbital energies of molecular organic semiconductors Org Electron 10 2009 515 520