The photo- and electrochemical properties and electronic structures of conjugated diphenylanthrazolines

Dyes and Pigments

Volumn 85, Issue 1-2, 2010, Pages 51-56

  Liu, Shan ^a   Wang, Qiang ^b   Jiang, Peng ^a   Liu, Rui ^a   Song, Guangliang ^a   Zhu, Hongjun ^a   Yang, Shuo Wang ^c  

^a NANJING TECH UNIVERSITY   (China)

^b Nanyang Technological University   (Singapore)

^c INSTITUTE OF HIGH PERFORMANCE COMPUTING   (Singapore)

Author keywords

Diphenylanthrazoline; Electrochemical property; Fluorescence; Optical property; Optoelectronic materials; Organic light emitting diodes (OLED)

Indexed keywords

ADSORPTION BANDS; DFT B3LYP/6; DIPHENYLANTHRAZOLINE; ELECTROCHEMICAL REDUCTIONS; EXCIMERS; OPTOELECTRONIC MATERIALS; PHOTOLUMINESCENCE EMISSION SPECTRA; PHOTOPHYSICAL; QUANTUM CHEMICAL CALCULATIONS; SATURATED CALOMEL ELECTRODE; STOKES SHIFT;

ADSORPTION; CURRENT DENSITY; CYCLIC VOLTAMMETRY; ELECTROCHEMICAL PROPERTIES; ELECTROLYTIC REDUCTION; ELECTRON AFFINITY; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; EMISSION SPECTROSCOPY; FLUORESCENCE; HELMET MOUNTED DISPLAYS; IONIZATION POTENTIAL; LIGHT EMISSION; LIGHT EMITTING DIODES; OPTICAL PROPERTIES; OPTOELECTRONIC DEVICES; PHOTOLUMINESCENCE; PHOTOLUMINESCENCE SPECTROSCOPY; QUANTUM CHEMISTRY;

ORGANIC LIGHT EMITTING DIODES (OLED);

ABSORPTION; ELECTROCHEMISTRY; MOLECULAR STRUCTURE; OPTICAL PROPERTY; PHYSICAL PROPERTY;

EID: 70449530601     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.10.003     Document Type: Article

References (43)

1. Tang C.W., and Vanslyke S.A. Organic electroluminescent diodes. Applied Physics Letters 51 12 (1987) 913-915
2. Burroughes J.H., Bradley D.D.C., Brown A.R., Marks R.N., Mackay K., Friend R.H., et al. Light-emitting-diodes based on conjugated polymers. Nature 347 6293 (1990) 539-541
3. Jenekhe S.A., and Osaheni J.A. Excimers and exciplexes of conjugated polymers. Science 265 5173 (1994) 765-768
4. Baldo M.A., O'Brien D.F., You Y., Shoustikov A., Sibley S., Thompson M.E., et al. Highly efficient phosphorescent emission from organic electroluminescent devices. Nature 395 6698 (1998) 151-154
5. Ho P.K.H., Kim J.S., Burroughes J.H., Becker H., Li S.F.Y., Brown T.M., et al. Molecular-scale interface engineering for polymer light-emitting diodes. Nature 404 6777 (2000) 481-484
6. Tonzola C.J., Alam M.M., Kaminsky W., and Jenekhe S.A. New n-type organic semiconductors: synthesis, single crystal structures, cyclic voltammetry, photophysics, electron transport, and electroluminescence of a series of diphenylanthrazolines. Journal of the American Chemical Society 125 44 (2003) 13548-13558
7. Brunner K., van Dijken A., Borner H., Bastiaansen J., Kiggen N.M.M., and Langeveld B.M.W. Carbazole compounds as host materials for triplet emitters in organic light-emitting diodes: tuning the homo level without influencing the triplet energy in small molecules. Journal of the American Chemical Society 126 19 (2004) 6035-6042
8. Granstrom M., Petritsch K., Arias A.C., Lux A., Andersson M.R., and Friend R.H. Laminated fabrication of polymeric photovoltaic diodes. Nature 395 6699 (1998) 257-260
9. Shirota Y. Organic materials for electronic and optoelectronic devices. Journal of Materials Chemistry 10 1 (2000) 1-25
10. Peumans P., Yakimov A., and Forrest S.R. Small molecular weight organic thin-film photodetectors and solar cells. Journal of Applied Physics 93 7 (2003) 3693-3723
11. Thompson B.C., Kim Y.G., McCarley T.D., and Reynolds J.R. Soluble narrow band gap and blue propylenedioxythiophene-cyanovinylene polymers as multifunctional materials for photovoltaic and electrochromic applications. Journal of the American Chemical Society 128 39 (2006) 12714-12725
12. Blom P.W.M., Mihailetchi V.D., Koster L.J.A., and Markov D.E. Device physics of polymer: fullerene bulk heterojunction solar cells. Advanced Materials 19 12 (2007) 1551-1566
13. Chochos C.L., Economopoulos S.P., Deimede V., Gregoriou V.G., Lloyd M.T., Malliaras G.G., et al. Synthesis of a soluble n-type cyano substituted polythiophene derivative: a potential electron acceptor in polymeric solar cells. Journal of Physical Chemistry C 111 28 (2007) 10732-10740
14. Gunes S., Neugebauer H., and Sariciftci N.S. Conjugated polymer-based organic solar cells. Chemical Reviews 107 4 (2007) 1324-1338
15. Wang S.J., Oldham W.J., Hudack R.A., and Bazan G.C. Synthesis, morphology, and optical properties of tetrahedral oligo(phenylenevinylene) materials. Journal of the American Chemical Society 122 24 (2000) 5695-5709
16. Cornil J., Beljonne D., Calbert J.P., and Bredas J.L. Interchain interactions in organic pi-conjugated materials: impact on electronic structure, optical response, and charge transport. Advanced Materials 13 14 (2001) 1053-1067
17. Dimitrakopoulos C.D., and Malenfant P.R.L. Organic thin film transistors for large area electronics. Advanced Materials 14 2 (2002) 99-117
18. Facchetti A., Mushrush M., Yoon M.H., Hutchison G.R., Ratner M.A., and Marks T.J. Building blocks for n-type molecular and polymeric electronics. Perfluoroalkyl-versus alkyl-functionalized oligothiophenes (nT; n = 2-6). Systematics of thin film microstructure, semiconductor performance, and modeling of majority charge injection in field-effect transistors. Journal of the American Chemical Society 126 42 (2004) 13859-13874
19. Newman C.R., Frisbie C.D., da Silva D.A., Bredas J.L., Ewbank P.C., and Mann K.R. Introduction to organic thin film transistors and design of n-channel organic semiconductors. Chemistry of Materials 16 23 (2004) 4436-4451
20. Murphy A.R., and Frechet J.M.J. Organic semiconducting oligomers for use in thin film transistors. Chemical Reviews 107 4 (2007) 1066-1096
21. Yoon M.H., DiBenedetto S.A., Russell M.T., Facchetti A., and Marks T.J. High-performance n-channel carbonyl-functionalized quaterthiophene semiconductors: thin-film transistor response and majority carrier type inversion via simple chemical protection/deprotection. Chemistry of Materials 19 20 (2007) 4864-4881
22. Forrest S.R. The path to ubiquitous and low-cost organic electronic appliances on plastic. Nature 428 6986 (2004) 911-918
23. Bracke W. Polymers with anthrazoline units in the main chain. Macromolecules 2 3 (1969) 286-289
24. Higgins J., and Janovi Z. Polyanthrazolines. Journal of Polymer Science Part B: Polymer Letters 10 5 (1972) 357-360
25. Imai Y., Johnson E.F., Katto T., Kurihara M., and Stille J.K. Synthesis of aromatic polymers containing anthrazoline and isoanthrazoline units. Journal of Polymer Science: Polymer Chemistry Edition 13 10 (1975) 2233-2249
26. Stille JK. US patent, 4000187. 1976.
27. Agrawal A.K., and Jenekhe S.A. New conjugated polyanthrazolines containing thiophene moieties in the main chain. Macromolecules 24 25 (1991) 6806-6808
28. Agrawal A.K., and Jenekhe S.A. Synthesis and processing of heterocyclic polymers as electronic, optoelectronic, and nonlinear optical materials. 2. New series of conjugated rigid-rod polyquinolines and polyanthrazolines. Macromolecules 26 5 (1993) 895-905
29. Jenekhe S, Agrawal A. WO Patent, 9404592-A. 1993.
30. Jenekhe SA, Osaheni JA. WO Patent, 9512628. 1995.
31. Agrawal A.K., and Jenekhe S.A. Electrochemical properties and electronic structures of conjugated polyquinolines and polyanthrazolines. Chemistry of Materials 8 2 (1996) 579-589
32. Hou S., Ding M., and Gao L.X. Synthesis and properties of polyquinolines and polyanthrazolines containing pyrrole units in the main chain. Macromolecules 36 11 (2003) 3826-3832
33. Rusanov A.L., Komarova L.G., Prigozhina M.P., and Likhatchev D.Y. Polyquinolines and polyanthrazolines: synthesis and properties. Uspekhi Khimii 74 7 (2005) 739-752
34. Glossman-Mitnik D., Barraza-Jimenez D., Flores-Hidalgo A., and Rodriguez-Valdez L.M. Molecular structure and substitution effects on diphenylanthrazolines for organic semiconductors: a theoretical study. Journal of Molecular Structure: THEOCHEM 863 1-3 (2008) 99-104
35. Liu S., Jiang P., Song G., Liu R., and Zhu H. Synthesis and optical properties of a series of thermally stable diphenylanthrazolines. Dyes and Pigments 81 3 (2009) 218-223
36. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., et al. Gaussian 03, revision D.01 (2004), Gaussian, Inc., Wallingford CT
37. Kohn W., and Sham L.J. Self-consistent equations including exchange and correlation effects. Physical Review 140 4A (1965) 1133-1138
38. Becke A.D. Density-functional thermochemistry .3. The role of exact exchange. Journal of Chemical Physics 98 7 (1993) 5648-5652
39. Lee C.T., Yang W.T., and Parr R.G. Development of the colle-salvetti correlation-energy formula into a functional of the electron-density. Physical Review B 37 2 (1988) 785-789
40. Osaheni J.A., and Jenekhe S.A. Efficient blue luminescence of a conjugated polymer exciplex. Macromolecules 27 3 (1994) 739-742
41. Yang C.J., and Jenekhe S.A. Conjugated aromatic polyimines. 2. Synthesis, structure, and properties of new aromatic polyazomethines. Macromolecules 28 4 (1995) 1180-1196
42. Hancock J.M., Gifford A.P., Tonzola C.J., and Jenekhe S.A. High-efficiency electroluminescence from new blue-emitting oligoquinolines bearing pyrenyl or triphenyl endgroups. Journal of Physical Chemistry 111 18 (2007) 6875-6882
43. Promarak V., Punkvuang A., Sudyoadsuk T., Jungsuttiwong S., Saengsuwan S., Keawin T., et al. Synthesis and characterization of N-carbazole end-capped oligofluorene-thiophenes. Tetrahedron 63 36 (2007) 8881-8890