Novel phenyl-oligothiophene derivatives containing acetylenic spacers for thin film materials: Synthesis, photophysical and morphology properties

Dyes and Pigments

Volumn 97, Issue 1, 2013, Pages 184-197

  Niu, Qingfen ^a   Lu, Yunqiang ^a   Sun, Hongjian ^a   Li, Xiaoyan ^a   Tao, Xutang ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Acetylenic spacer; Morphology; Phenyl oligothiophene derivative; Photovoltaic device; Thin film material; Thiophene

Indexed keywords

ACETYLENIC SPACER; CRYSTALLINITIES; ELECTROCHEMICAL MEASUREMENTS; ETHYNYL; FILM MORPHOLOGY; FLUORESCENCE PROPERTIES; INTERMOLECULAR INTERACTIONS; LIQUID CRYSTALLINE PROPERTIES; MORPHOLOGICAL PROPERTIES; OPTOELECTRIC FIELDS; ORGANIC THIN FILMS; PHENYLETHYNYL; PHOTOPHYSICAL; PHOTOVOLTAIC DEVICES; PHOTOVOLTAIC MATERIALS; QUATERTHIOPHENE; SINGLE-CRYSTALLINE; TERTHIOPHENES; TGA AND DSC; THIN FILM MATERIAL; UV-VIS SPECTRA; XRD; XRD ANALYSIS;

ANILINE; CRYSTALLINE MATERIALS; MOLECULES; OLIGOMERS; OPTICAL MICROSCOPY; SELF ASSEMBLY; THIN FILMS; THIOPHENE;

MORPHOLOGY;

EID: 84873391223     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.12.012     Document Type: Article

References (47)

1. C.D. Dimitrakopoulos, and P.R.L. Malenfant Organic thin film transistors for large area electronics Adv Mater 14 2002 99 117
2. A.R. Murphy, and J.M.J. Fréchet Organic semiconducting oligomers for use in thin film transistors Chem Rev 107 2007 1066 1096
3. Y. Shirota, and H. Kageyama Charge carrier transporting molecular materials and their applications in devices Chem Rev 107 2007 953 1010
4. J. Cornil, D. Beljonne, J.-P. Calbert, and J.-L. Brédas Interchain interactions in organic π-conjugated materials: impact on electronic structure, optical response, and charge transport Adv Mater 13 2001 1053 1067
5. X. Yang, L. Wang, C. Wang, W. Long, and Z. Shuai Influences of crystal structures and molecular sizes on the charge mobility of organic semiconductors: oligothiophenes Chem Mater 20 2008 3205 3211
6. D. Fichou, and C. Ziegler Structure and properties of oligothiophenes in the solid state: single crystals and thin films Handbook of oligo- and Polythiophenes 1999 183 282
7. D. Fichou Structural order in conjugated oligothiophenes and its implications on opto-electronic devices J Mater Chem 10 2000 571 588
8. A.R. Murphy, J.M.J. Fréchet, P. Chang, J. Lee, and V. Subramanian Organic thin film transistors from a soluble oligothiophene derivative containing thermally removable solubilizing groups J Am Chem Soc 126 2004 1596 1597
9. R.J. Chesterfield, C.R. Newman, T.M. Pappenfus, P.C. Ewbank, M.H. Haukaas, and K.R. Mann High electron mobility and ambipolar transport in organic thin-film transistors based on a π-stacking quinoidal terthiophene Adv Mater 15 2003 1278 1282
10. A. Facchetti, M.H. Yoon, C.L. Stern, H.E. Katz, and T.J. Marks Building blocks for n-type organic electronics: regiochemically modulated inversion of majority carrier sign in perfluoroarene-modified polythiophene semiconductors Angew Chem Int Ed Engl 42 2003 3900 3903
11. M. Halik, H. Klauk, U. Zshieschang, G. Schmid, S. Ponomarenko, and S. Kirchmeyer Relationship between molecular structure and electrical performance of oligothiophene organic thin film transistors Adv Mater 15 2003 917 922
12. H.Z. Katz, Z.N. Bao, and S.L. Gilat Synthetic chemistry for ultrapure, processable, and high-mobility organic transistor semiconductors Acc Chem Res 34 2001 359 369
13. Z.H. Li, M.S. Wong, H. Fukutani, and Y. Tao Full emission color tuning in bis-dipolar diphenylamino-endcapped oligoarylfluorenes Chem Mater 17 2005 5032 5040
14. Q. Meng, J. Gao, R. Li, L. Jiang, C. Wang, and H. Zhao New type of organic semiconductors for field-effect transistors with carbon-carbon triple bonds J Mater Chem 19 2009 1477 1482
15. A.K. Diallo, C. Videlot-Ackermann, P. Marsal, H. Brisset, F. Fages, and A. Kumagai Acetylenic spacers in phenylene end-substituted oligothiophene core for highly air-stable organic field-effect transistors Phys Chem Chem Phys 12 2010 3845 3851
16. R.A.K. Diallo, F. Fages, F. Serein-Spirau, J.-P. Lere-porte, and C. Videlot-Ackermann Effect of molecular structure on bias stress effect in organic thin-film transistors Appl Surf Sci 257 2011 9386 9389
17. H. Wang, H.S. Lim, S. Kim, J. Lim, C. Lee, and D.W. Kim Oliogothiophenes end-capped with arylacetylenes for organic thin film transistors Synth Met 159 2009 2564 2570
18. H. Hoppe, D.A.M. Egbe, D. Mühlbacher, and N.S. Sariciftci Photovoltaic action of conjugated polymer/fullerene bulk heterojunction solar cells using novel PPE-PPV copolymers J Mater Chem 14 2004 3462 3467
19. D.A.M. Egbe, L.H. Nguyen, D. Mühlbacher, H. Hoppe, and K. Dchmidtke SariciftciNS. Photophysical, electrochemical and photovoltaic properties of thiophene-containing arylene-ethynylene/arylene-vinylene polymers Thin Solid Films 2006 511 512 486-8
20. A. Marrocchi, F. Silvestri, M. Seri, A. Facchetti, A. Taticchi, and T.J. Marks Conjugated anthracene derivatives as donor materials for bulk heterojunction solar cells: olefinic versus acetylenic spacers Chem Commun 11 2009 1380 1382
21. J.K. Kochi, and G.S. Hammond Benzyl tosylates. III. The relative conjugative aptitudes of the acetylenic and ethylenic bonds J Am Chem Soc 75 1953 3452 3458
22. T. Yamamoto, W. Tamada, M. Takagi, K. Kizu, and T. Maruyama π-conjugated soluble poly(aryleneethynylene) type polymers. Preparation by palladium-catalyzed coupling reaction, nonlinear optical properties, doping, and chemical reactivity Macromolecules 27 1994 6620 6626
23. S. Leroy-Lhez, M. Allain, J. Oberle, and F. Fages Synthesis and zinc(II) complexation modulated fluorescence emission properties of two pyrene-oligo(phenylene vinylene)-2,2′-bipyridine conjugated molecular rods New J Chem 31 2007 1013 1021
24. V.A.L. Roy, Y.-G. Zhi, Z.-X. Xu, S.-C. Yu, P.W.H. Chan, and C.-M. Che Functionalized arylacetylene oligomers for organic thin-film transistors (OTFTs) Adv Mater 17 2005 1258 1261
25. N.S. Baek, S.K. Hau, H.-L. Yip, O. Acton, K.-S. Chen, and A.K.-Y. Jen High performance amorphous metalated π-conjugated polymers for field-effect transistors and polymer solar cells Chem Mater 20 2008 5734 5736
26. A. Marrocchi, M. seri, C. Kim, A. Facchetti, A. Taticchi, and T. Marks Low-dimensional arylacetylenes for solution-processable organic field-effect transistors Chem Mater 21 2009 2592 2594
27. P. Ostoja, P. Maccagnani, M. Gazzano, M. Cavallini, J.C. Kengne, and R. Kshirsagar FET device performance, morphology and X-ray thin film structure of unsubstituted and modified quinquethiophenes Synth Met 146 2004 243 250
28. M. Melucci, G. Barbarella, M. Zambianchi, P. Di Pietro, and A. Bongini Solution-phase microwave-assisted synthesis of unsubstituted and modified alpha-quinque- and sexithiophenes J Org Chem 69 2004 4821 4828
29. A.J.J.M. van Breemen, P.T. Herwig, C.H.T. Chlon, J. Sweelssen, H.F.M. Schoo, and S. Setayesh Large area liquid crystal monodomain field-effect transistors J Am Chem Soc 128 2006 2336 2345
30. M. Ashizawa, R. Kato, Y. Takanishi, and H. Takezoe Synthesis and solution-processed field effect transistors of liquid crystalline oligothiophenes Chem Lett 36 2007 708 709
31. O. Lavastre, L. Ollivier, and P.H. Dixneuf Sequential catalytic synthesis of rod-like conjugated poly-ynes Tetrahedron 52 1996 5495 5504
32. 4 as efficient iodination reagent for deactivated aromatic compounds Zh Org Khim 37 2001 1503 1504
33. D. Sahu, H. Padhy, D. Patra, D. Kekuda, C.-W. Chu, and I.-H. Chiang Synthesis and application of H-Bonded cross-linking polymers containing a conjugated pyridyl H-acceptor side-chain polymer and various carbazole-based H-donor dyes bearing symmetrical cyanoacrylic acids for organic solar cells Polymer 51 2010 6182 6192
34. Y.W. Li, Z.F. Li, C.Y. Wang, H. Li, H.G. Lu, and B. Xu Novel low-band gap oligothiophene-based donor-acceptor alternating conjugated copolymers: synthesis, properties, and photovoltaic applications J Polym Sci Part A Polym Chem 48 2010 2765 2776
35. L. Guan, J. Wang, J. Huang, C.Y. Jiang, M. La, and P. Liu Synthesis and photovoltaic properties of donor-acceptor oligothiophene derivatives possessing mesogenic properties Synth Commun 41 2011 3662 3670
36. A. Schoenberg, I. Bartoletti, and R.F. Heck Palladium-catalyzed carboalkoxylation of aryl, benzyl, and vinylic halides J Org Chem 39 1974 3318 3326
37. J.A.S. Bomfim, F.P. de Souza, C.A.L. Filgueiras, A.G. de Sousa, and M.T.P. Gambardella Diphosphine complexes of nickel: analogies in molecular structures and variety in crystalline arrangement Polyhedron 22 2003 1567 1573
38. Y. Xiao, T.-S. Chung, H.M. Guan, and M.D. Guiver Synthesis, cross-linking and carbonization of co-polyimides containing internal acetylene units for gas separation J Membr Sci 302 2007 254 264
39. M.P. Stevens Polymer chemistry, an introduction 1999 Oxford University Press New York
40. G. Barbarella, L. Favaretto, M. Zambianchi, O. Pudova, C. Arbizzani, and A. Bongini From easily oxidized to easily reduced thiophene-based materials Adv Mater 10 1998 551 554
41. Z.S. Wang, N. Koumura, Y. Cui, M. Takahashi, H. Sekugichi, and A. Mori Hexylthiophene-functionalized carbazole dyes for efficient molecular photovoltaics: tuning of solar-cell performance by structural modification Chem Mater 20 2008 3993 4003
42. D. Kim, J.K. Lee, S.O. Kang, and J. Ko Molecular engineering of organic dyes containing N-aryl carbazole moiety for solar cell Tetrahedron 63 2007 1913 1922
43. W. Yue, Y. Zhao, S. Shao, H. Tian, Z. Xie, and Y. Geng Novel NIR-absorbing conjugated polymers for efficient polymer solar cells: effect of alkyl chain length on device performance J Mater Chem 19 2009 2199 2206
44. A. Yassar, G. Horowitz, P. Valat, V. Wintgens, M. Hmyene, and F. Deloffre Exciton coupling effects in the absorption and photoluminescence of sexithiophene derivatives J Phys Chem 99 1995 9155 9159
45. Z. Wang, H. Shao, J. Ye, L. Tang, and P. Lu Dibenzosuberenylidene-ended fluorophores: rapid and efficient synthesis, characterization, and aggregation-induced emissions J Phys Chem B 109 2005 19627 19633
46. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 03, revision A. 1 2004 Gaussian, Inc. Pittsburgh, PA
47. D. Fichou Handbook of oligo- and poly-thiophenes 1999 Willey New York