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Spectroscopic and Morphological Properties of Divinylbenzoxazolylbiphenyl Thin Films

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Abstract

The thin organic films based on 4,4′-bis-[(Z)-1-(1,3-benzoxazol-2-yl-2-ethenyl)]biphenyl and its partly fluorinated derivatives are studied. Absorption, luminescence, and excitation spectra, luminescence decay and film morphology were found to depend sensitively on the changes in molecule structure, nature and temperature of the substrate, as well as the thermovacuum deposition rate, being the origins of bad reproducibility of the optical properties of such films. Molecular aggregation with chromophore dipoles arranged parallel to each other has been observed in absorption and luminescence spectra. The fluorescence characteristics can be explained by the combination of radiation of aggregated and non-aggregated molecules. The main characteristics of the molecules under study are calculated using DFT approach. The unusual behaviour of photodegradation in fluorinated film is found.

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References

  1. Kukhta AV (2003) Electroluminescence of thin films of organic compounds. J Appl Spectrosc 70:165–194. doi:10.1023/A:1023819931571

    Article  Google Scholar 

  2. Nalwa HS (ed) (2006) Handbook of organic electronics and photonics. American Scientific, Los Angeles

    Google Scholar 

  3. Akcelrud L (2003) Electroluminescent polymers. Prog Polym Sci 28:875–962. doi:10.1016/S0079-6700(02)00140-5

    Article  CAS  Google Scholar 

  4. Leising G, Tasch S, Graupner W (1997) In Skothem T, Elsenbaumer R, Reynolds J (eds) Handbook of conducting polymers, Marcel Dekker, New York, pp 847–880

  5. Balzer F, Rubahn H-G (2001) Dipole-assisted self-assembly of light-emitting p-np needles on mica. Appl Phys Lett 79:3860–3862. doi:10.1063/1.1424071

    Article  CAS  Google Scholar 

  6. Okajima T, Narioka S, Tanimura S, Hamano K, Kurata T, Uehara Y, Araki T, Ishii H, Ouchi Y, Seki K, Ogama T, Koezuka H (1996) NEXAFS spectroscopic studies of molecular orientation in α-sexithienyl evaporated thin films on metal films. J Electron Spectrosc Relat Phenom 78:379–382. doi:10.1016/S0368-2048(96)80103-4

    Article  CAS  Google Scholar 

  7. Kiguchi M, Yoshikawa G, Saiki K (2003) Temperature and thickness dependence of molecular orientation of a-sexithienyl on Cu(111). J Appl Phys 94:4866–4870. doi:10.1063/1.1609637

    Article  CAS  Google Scholar 

  8. Chaplanova ZD, Mihailovski YK, Agabekov VE, Olkhovik VK, Galinovskii NA, Gracheva EA (2007) Morphology and spectral properties of thin films of benzoxazole derivatives of biphenyl. J Appl Spectrosc 74(3):333–337. doi:10.1007/s10812-007-0054-3

    Article  CAS  Google Scholar 

  9. Kukhta AV, Kolesnik EE, Kukhta IN, Dudko EV, Tolkachev VA, Osipov KA, Pavlovskii VN, Olkhovik VK, Galinovskii NA (2008) Effect of temperature and oxygen on luminescence spectra and polarization of divinylbenzoxazolylbiphenyl thin films. J Fluorescence 18:633–637. doi:10.1007/s10895-008-0325-2

    Article  CAS  Google Scholar 

  10. Dudko EV, Kalosha II, Kukhta AV, Kukhta IN, Tolkachev VA, Olkhovik VK, Vasilevskii DA (2008) Anomaly in oxygen quenching of electron-excited states in 4, 4’-bis[2-(1, 3-benzoxazole-2-yl)ethenyl]biphenyl vapors. J Appl Spectrosc 75:902–905. doi:10.1007/s10812-009-9115-0

    Article  Google Scholar 

  11. Hosokawa C, Higashi H, Nakamura H, Kusumoto T (1995) Highly efficient blue electroluminescence from a distyrylarylene emitting layer with a new dopant. Appl Phys Lett 67(26):3853–3855. doi:10.1063/1.115295

    Article  CAS  Google Scholar 

  12. Sakamoto Y, Suzuki T, Kobayashi M, Gao Y, Fukai Y, Inoue Y, Sato F, Tokito S (2004) Perfluoropentacene: high-performance p–n junctions and complementary circuits with pentacene. J Am Chem Soc 126:8138–8140. doi:10.1021/ja0476258

    Article  CAS  PubMed  Google Scholar 

  13. Olkhovik VK, Pap AA, Vasilevskii VA, Galinovskii NA, Tereshko SN (2008) Synthesis and properties of luminophores derived from fluorinated biphenyls. Russ J Org Chem 44:1172–1179. doi:10.1134/S1070428008080113

    Article  CAS  Google Scholar 

  14. Frisch MJ, Trucks GW, Schlegel HB et al (2004) Gaussian 03, Revision D.01. Gaussian, Inc, Wallingford CT

    Google Scholar 

  15. Vlček A Jr, Záliš S (2007) Modelling of charge-transfer transitions and excited states in d6 transition metal complexes by DFT techniques. Coord Chem Rev 251:258–287. doi:10.1016/j.ccr.2006.05.021

    Article  Google Scholar 

  16. Wu C, Tretiak S, Chernyak VY (2007) Excited states and optical response of a donor-acceptor substituted polyene: a TD-DFT study. Chem Phys Lett 433:305–311. doi:10.1016/j.cplett.2006.11.069

    Article  CAS  Google Scholar 

  17. Kukhta AV, Kukhta IN, Bagnich SA, Kazakov SM, Andreev VA, Neyra OL, Meza E (2007) Interactions of low-energy electrons with Ir(ppy)3 in the gas phase. Chem Phys Lett 434:11–14. doi:10.1016/j.cplett.2006.11.096

    Article  CAS  Google Scholar 

  18. Wang J-F, Feng J-K (2007) Theoretical studies of the structures and optical properties of the bifluorene and its derivatives. J Phys Org Chem 20:130–137. doi:10.1002/poc.1135

    Article  CAS  Google Scholar 

  19. Medina BM, Beljonne D, Egelhaaf H-J, Gierschner J (2007) Effect of fluorination on the electronic structure and optical excitations of π-conjugated molecules. J Chem Phys 126:111101–111106. doi:10.1063/1.2713096

    Article  Google Scholar 

  20. Kim BJ, Park SY, Choi DH (2001) Effect of molecular aggregation on the photo-induced anisotropy in amorphous polymethacrylate bearing an aminonitroazobenzene moiety. Bull Korean Chem Soc 22:271–275

    CAS  Google Scholar 

  21. Frolov SV, Kloc C, Batlogg B, Wohlgenannt M, Jiang X, Vardeny ZV (2001) Excitation dynamics in single molecular crystals of α-hexathiophene from femtoseconds to milliseconds. Phys Rev B 63(20):205203. doi:10.1103/PhysRevB.63.205203

    Article  Google Scholar 

  22. Antolini L, Horovitz G, Kouki F, Garnier F (1998) Polymorphism in oligothiophenes with an even number of thiophene subunits. Adv Mater 10:382–385. doi:10.1002/(SICI)1521-4095(199803)10:5<382::AID-ADMA382>3.0.CO;2-Y

    Article  CAS  Google Scholar 

  23. Claes L, François JP, Deleuze MS (2001) Molecular packing of oligomer chains of poly(p-phenylene vinylene). Chem Phys Lett 339:216–222. doi:10.1016/S0009-2614(01)00300-1

    Article  CAS  Google Scholar 

  24. Davydov AS (1971) Theory of molecular excitons. Plenum, New York

    Google Scholar 

  25. Plank H, Resel R, Andreev A, Sariciftci NS, Sitter H (2002) Structural relationship between epitaxially grown para-sexiphenyl and mica (0 0 1) substrates. J Cryst Growth 237–239:2076–2081. doi:10.1016/S0022-0248(01)02313-2

    Article  Google Scholar 

  26. Bohn PW (1993) Aspects of structure and energy transport in artificial molecular assemblies. Annu Rev Phys Chem 44:37–60. doi:10.1146/annurev.pc.44.100193.000345

    Article  CAS  Google Scholar 

  27. Terenin AN (1967) Molecular photonics of dyes and relative compounds (in Russian). Science, Leningrad

    Google Scholar 

  28. Spano FC, Siddiqui S (1999) Exciton-vibrational coupling in pinwheel aggregates of π-conjugated molecules. Chem Phys Lett 314:481–487. doi:10.1016/S0009-2614(99)01078-7

    Article  CAS  Google Scholar 

  29. Spano FC (2000) Emission from aggregates of oligo-phenylene vinylenes: a recipe for superradiant H-aggregates. Chem Phys Lett 331:7–13. doi:10.1016/S0009-2614(00)01153-2

    Article  CAS  Google Scholar 

  30. Knupfer M, Schwieger T, Fink J, Leo K, Hoffmann M (2002) Excitons in quasi-one-dimensional organic crystals. Phys Rev B66:035208

    Google Scholar 

  31. Göötz B, Kröhl O, Swiderek P (2001) High-resolution electron-energy-loss spectroscopy of molecular multilayer film growth and properties. J Electron Spectr Rel Phenom 114–116:569–574. doi:10.1016/S0368-2048(00)00251-6

    Article  Google Scholar 

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Kukhta, A.V., Kukhta, I.N., Kolesnik, E.E. et al. Spectroscopic and Morphological Properties of Divinylbenzoxazolylbiphenyl Thin Films. J Fluoresc 19, 989–996 (2009). https://doi.org/10.1007/s10895-009-0498-3

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  • DOI: https://doi.org/10.1007/s10895-009-0498-3

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