Synthesis and photoluminescent properties of conjugated aryl-vinyl dioctyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate derivatives

Dyes and Pigments

Volumn 99, Issue 3, 2013, Pages 803-811

  Bosiak, Mariusz J ^a   Rakowiecki, Marcin ^a   Orłowska, Katarzyna J ^a   Kȩdziera, Dariusz ^a   Adams, Jörg ^b  

^a NICOLAUS COPERNICUS UNIVERSITY   (Poland)

^b CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Benzodifuran; Fluorescence; Heteroaryl compounds OLED; The Heck reaction; The Wittig reaction

Indexed keywords

BENZODIFURAN; ETHYLACETOACETATE; HECK REACTIONS; HETEROARYL COMPOUNDS; PHOTO-LUMINESCENT PROPERTIES; TRANSESTERIFICATION REACTION; UV-VIS FLUORESCENCES; WITTIG REACTION;

AROMATIC COMPOUNDS; FLUORESCENCE; ORGANIC POLLUTANTS; STYRENE; SYNTHESIS (CHEMICAL);

CARBOXYLATION;

EID: 84882472848     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.07.006     Document Type: Article

References (47)

1. C. Hilsum Flat-panel electronic displays: a triumph of physics, chemistry and engineering Philos Transact A Math Phys Eng Sci 368 2010 1027 1082
2. J.W. Park, D.C. Shin, and S.H. Park Large-area OLED lightings and their applications Semicond Sci Technol 26 2011 034002 [9 pp]
3. B. Szyszka, W. Dewald, S.K. Gurram, A. Pflug, C. Schulz, and M. Siemers Recent developments in the field of transparent conductive oxide films for spectral selective coatings, electronics and photovoltaics Curr Appl Phys 12 2012 S2 S11
4. J.S. Park, W.J. Maeng, H.S. Kim, and J.S. Park Review of recent developments in amorphous oxide semiconductor thin-film transistor devices Thin Solid Films 520 2012 1679 1693
5. F. So, J. Kido, and P. Burrows MRS Bull 33 2008 663 669
6. U. Lafont, H. Zeijl, and S. Zwaag Increasing the reliability of solid state lighting systems via self-healing approaches: a review Microelectron Reliab 52 2012 71 89
7. T.N. Kalyania, and S.J. Dhoble Organic light emitting diodes: energy saving lighting technology - a review Renev Sust Energ Rev 6 2012 2696 2723
8. A.R. Duagal, C.M. Heller, J.J. Shiang, J. Liu, and L.N. Lewis Solution-processed organic light-emitting diodes for lighting J Display Technol 3 2007 184 192 (Pubitemid 46808674)
9. C. Hosokawa, H. Higashi, H. Nakamura, and T. Kusumoto Highly efficient blue electroluminescence from a distyrylarylene emitting layer with a new dopant Appl Phys Lett 67 1995 3853 3855
10. M. Strukeji, R.H. Jordan, and A. Dodabalapur Organic multilayer white light emitting diodes J Am Chem Soc 118 1996 1213 1214 (Pubitemid 26075551)
11. Z.Q. Gao, C.S. Lee, I. Bello, and S.T. Lee Bright-blue electroluminescence from a silyl-substituted ter-(phenylene-vinylene) derivative Appl Phys Lett 74 1999 865 867 (Pubitemid 129615207)
12. C. Hosokawa, H. Tokailin, H. Higashi, and T. Kusumoto Efficient electroluminescence of distyrylarylene with hole transporting ability J Appl Phys 78 1995 5831 5833
13. X.T. Tao, H. Suzuk, T. Wada, H. Sasabe, and S. Miyata Lithium tetra-(8-hydroxy-quinolinato) boron for blue electroluminescent applications Appl Phys Lett 75 1999 1655 1658
14. B.X. Mi, Z.Q. Gao, C.S. Lee, and S.T. Lee Reduction of molecular aggregation and its application to the high-performance blue perylene-doped organic electroluminescent device Appl Phys Lett 75 1999 4055 4057 (Pubitemid 129709754)
15. W.L. Yu, Y. Cao, J. Pei, W. Huang, and A.J. Heeger Blue polymer light-emitting diodes from poly(9,9-dihexylfluorene-alt-co-2,5-didecyloxy-para- phenylene) Appl Phys Lett 75 1999 3270 3272 (Pubitemid 129564622)
16. X.Z. Jiang, S. Liu, and H. Ma High-performance blue light-emitting diode based on a binaphthyl-containing polyfluorene Appl Phys Lett 76 2000 1813 1815
17. C.W. Lee, H.W. Rhee, C. Kim, and M.S. Gong Chemiluminescent properties of fluorene- and carbazole-containing polymeric fluorophores Bull Korean Chem Soc 21 2000 701 704
18. N.C. Seong, Y.M. Jeon, T.H. Lim, J.W. Kim, C.W. Lee, and E.J. Lee Organic light-emitting device using new distyrylarylene host materials Synth Met 157 2007 421 426
19. K. Mullen, and G. Wegner Electronic materials: the oligomer approach 1998 Wiley-VCH Weinheim, Germany
20. K. Mullen, and U. Scherf Organic-light emitting devices: synthesis, properties and applications 2006 Wiley-VCH Weinheim, Germany
21. Z. Li, and H. Meng Organic light-emitting materials and devices 2007 Taylor & Francis Boca Raton, London, New York
22. A. Guerlin, F. Dumur, E. Dumas, F. Miomandre, G. Wantz, and C.R. Mayer Tunable optical properties of chromophores derived from oligo(p-phenylene vinylene) Org Lett 12 2010 2382 2385
23. S.S. Babu, V.K. Praveen, S. Prasanthkumar, and A. Ajayaghoshi Self-assembly of oligo(para-phenylenevinylene)s through arene - perfluoroarene interactions: π gels with longitudinally controlled fiber growth and supramolecular exciplex-mediated enhanced emission Chem Eur J 14 2008 9577 9584
24. A. Chaieb, L. Vignau, R. Brown, G. Wantz, N. Huby, and J. Francois PL and EL properties of oligo(p-phenylene vinylene) (OPPV) derivatives and their applications in organic light-emitting diodes (OLED) Opt Mater 31 2008 68 74
25. H. Tsuji, C. Mitsui, Y. Sato, and E. Nakamura Bis(carbazolyl) benzodifuran: a high-mobility ambipolar material for homojunction organic light-emitting diode devices Adv Mater 21 2009 3776 3779
26. H. Tsuji, C. Mitsui, L. Ilies, Y. Sato, and E. Nakamura Synthesis and properties of 2,3,6,7-tetraarylbenzo[1,2-b:4,5-b′]difurans as hole-transporting material J Am Chem Soc 129 2007 11902 11903 (Pubitemid 47512012)
27. N. Hayashi, Y. Saito, H. Higuchi, and K. Suzuki Comparative studies on electronic spectra and redox behaviors of isomeric benzo[1,2-b:4,5-b′] difurans and benzo[1,2-b:5,4-b′]difurans J Phys Chem A 113 2009 5342 5347
28. C. Moussallem, F. Gohier, C. Mallet, M. Allain, and P. Frère Extended benzodifuran-furan derivatives as example of π-conjugated materials obtained from sustainable approach Tetrahedron 68 2012 8617 8621
29. Yi Ch, C. Blum, M. Lehmann, S. Keller, S. Liu, and G. Frei Versatile strategy to access fully functionalized benzodifurans: redox-active chromophores for the construction of extended p-conjugated materials J Org Chem 75 2010 3350 3357
30. U. Caruso, B. Panunzi, G.N. Roviello, G. Roviello, M. Tingoli, and A. Tuzi Synthesis, structure and reactivity of amino-benzodifurane derivatives C R Chim 12 2009 622 634
31. R. Shukla, S.H. Wadumethrige, S.V. Lindeman, and R. Rathore Synthesis, electronic properties, and X-ray structural characterization of tetraarylbenzo[1,2-b: 4,5-b′]difuran cation radicals Org Lett 10 2008 3587 3590
32. J. Santos-Pérez, C.E. Crespo-Hernández, C. Reichardt, C.R. Cabrera, I. Feliciano-Ramos, and L. Arroyo-Ramírez Synthesis, optical characterization, and electrochemical properties of isomeric tetraphenylbenzodifurans containing electron acceptor groups J Phys Chem A 115 2011 4157 4168
33. H. Liu, P. Jiang, C. Yi, S.X. Liu, S. Tan, and B. Zhao Benzodifuran-based π-conjugated copolymers for bulk heterojunction solar cells Macromolecules 43 2010 8058 8062
34. C. Yi, C. Blum, M. Lehmann, S. Keller, S.X. Liu, and G. Frei Versatile strategy to access fully functionalized benzodifurans: redox-active chromophores for the construction of extended pi-conjugated materials J Org Chem 75 2010 3350 3357
35. M.J. Bosiak, J.A. Jakubowska, K.B. Aleksandrzak, S. Kamiński, A. Kaczmarek-Kȩdziera, and M. Ziegler-Borowska Synthesis of a new class of highly fluorescent aryl-vinyl benzo[1,2-b:4,5-b′]difuran derivatives Tetrahedron Lett 53 2012 3923 3926
36. K. Kadac, M.J. Bosiak, and J. Nowaczyk Synthesis and AC impedance studies of 2,6-distyrylbenzofuro[5,6-b]furan based new organic semiconductor Synth Met 162 2012 1981 1986
37. R. Ottanà, R. Maccari, M. Giglio, A. Del Corso, M. Cappiello, and U. Mura Identification of 5-arylidene-4-thiazolidinone derivatives endowed with dual activity as aldose reductase inhibitors and antioxidant agents for the treatment of diabetic complications Eur J Med Chem 46 2011 2797 2806
38. B.R. Kim, H.G. Lee, E.J. Kim, S.G. Lee, and Y.J. Yoon Conversion of oximes to carbonyl compounds with 2-Nitro-4,5-dichloropyridazin-3(2H)-one J Org Chem 75 2010 484 486
39. G.P. Schiemenz, and J. Thobe Aromatische Phosphine mit Substituenten zweiter Ordnung, III. Eine neue Variante der Wittig-Reaktion Chem Ber 99 1966 2663 2668
40. H.J. Xu, Y.Q. Zhao, and X.F. Zhou Palladium-catalyzed Heck reaction of aryl chlorides under mild conditions promoted by organic ionic bases J Org Chem 76 2011 8036 8041
41. G. Manecke, and S. Luettke Über Synthesen einiger oligomerer substituierter Arylenvinylene Chem Ber 103 1970 700 707
42. X. Wu, A.P. Davis, and A.J. Fry Electrocatalytic oxidative cleavage of electron-deficient substituted stilbenes in acetonitrile-water employing a new high oxidation potential electrocatalyst. An electrochemical equivalent of ozonolysis Org Lett 9 2007 5633 5636
43. I. Cepanec, A. Živković, A. Bartolinčić, H. Mikuldaš, M. Litvić, and S. Merkaš Potassium phosphate/benzyltriethylammonium chloride as efficient catalytic system for transesterification Croat Chem Acta 81 2008 519 523
44. 2 as an active catalyst revisited J Org Chem 68 2003 7528 7531 (Pubitemid 37122512)
45. R. Antonioletti, F. Bonadies, A. Ciammaichella, and A. Viglianti Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis Tetrahedron 64 2008 4644 4648
46. S. Glazier, J.A. Barron, N. Morales, A.M. Ruschak, P.L. Houston, and H.D. Abrun Quenching dynamics of the photoluminescence of [Ru(bpy)3]2+-pendant PAMAM dendrimers by nitro aromatics and other materials Macromolecules 36 2003 1272 1278
47. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 09, revision A.02 2009 Gaussian, Inc. Wallingford CT