Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2016, Article ID 9360230, 14 pages
http://dx.doi.org/10.1155/2016/9360230
Research Article

Synthesis of Novel Derivatives of Carbazole-Thiophene, Their Electronic Properties, and Computational Studies

1Chemistry Department, Science Faculty, University of Malaya, 50603 Kuala Lumpur, Malaysia
2Physic Department, Science Faculty, University of Malaya, 50603 Kuala Lumpur, Malaysia

Received 10 January 2016; Accepted 6 April 2016

Academic Editor: Davut Avci

Copyright © 2016 E. F. Damit et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. A. Mishra and P. Bäuerle, “Small molecule organic semiconductors on the move: promises for future solar energy technology,” Angewandte Chemie International Edition, vol. 51, no. 9, pp. 2020–2067, 2012. View at Google Scholar
  2. H. Klauk, Organic Electronics: Materials, Manufacturing, and Applications, John Wiley & Sons, New York, NY, USA, 2006.
  3. K. Müllen and U. Scherf, Eds., Organic Light Emitting Devices: Synthesis, Properties and Applications, Wiley-VCH, Weinheim, Germany, 2006. View at Publisher · View at Google Scholar
  4. T. J. J. Muller and U. H. F. Bunz, Functional Organic Materials: Syntheses, Strategies and Applications, Wiley-VCH, Weinheim, Germany, 2007.
  5. Z. H. Kafafi, Organic Electroluminescence, CRC Press, New York, NY, USA, 2005.
  6. M. M. Haley and R. R. Tykwinski, Carbon-Rich Compounds: from Molecules to Materials, John Wiley & Sons, New York, NY, USA, 2006.
  7. T. W. Kelley, P. F. Baude, C. Gerlach et al., “Recent progress in organic electronics: materials, devices, and processes,” Chemistry of Materials, vol. 16, no. 23, pp. 4413–4422, 2004. View at Publisher · View at Google Scholar · View at Scopus
  8. S. R. Forrest and M. E. Thompson, “Introduction: organic electronics and optoelectronics,” Chemical Reviews, vol. 107, no. 4, pp. 923–925, 2007. View at Publisher · View at Google Scholar · View at Scopus
  9. M. Bendikov, F. Wudl, and D. F. Perepichka, “Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: the brick and mortar of organic electronics,” Chemical Reviews, vol. 104, no. 11, pp. 4891–4945, 2004. View at Publisher · View at Google Scholar · View at Scopus
  10. Y. Shirota and H. Kageyama, “Charge carrier transporting molecular materials and their applications in devices,” Chemical Reviews, vol. 107, no. 4, pp. 953–1010, 2007. View at Publisher · View at Google Scholar · View at Scopus
  11. W. Wu, Y. Liu, and D. Zhu, “π-Conjugated molecules with fused rings for organic field-effect transistors: design, synthesis and applications,” Chemical Society Reviews, vol. 39, no. 5, pp. 1489–1502, 2010. View at Publisher · View at Google Scholar · View at Scopus
  12. N. J. Tao, “Electron transport in molecular junctions,” Nature nanotechnology, vol. 1, no. 3, pp. 173–181, 2006. View at Publisher · View at Google Scholar · View at Scopus
  13. J. C. Cuevas and E. Scheer, Molecular Electronics: An Introduction to Theory and Experiment, vol. 1, World Scientific, River Edge, NJ, USA, 2010.
  14. J. V. Grazulevicius, P. Strohriegl, J. Pielichowski, and K. Pielichowski, “Carbazole-containing polymers: synthesis, properties and applications,” Progress in Polymer Science, vol. 28, no. 9, pp. 1297–1353, 2003. View at Publisher · View at Google Scholar · View at Scopus
  15. J.-F. Morin, M. Leclere, D. Adès, and A. Siove, “Polycarbazoles: 25 years of progress,” Macromolecular Rapid Communications, vol. 26, no. 10, pp. 761–778, 2005. View at Publisher · View at Google Scholar · View at Scopus
  16. N. Blouin and M. Leclerc, “Poly(2,7-carbazole)s: structure-property relationships,” Accounts of Chemical Research, vol. 41, no. 9, pp. 1110–1119, 2008. View at Publisher · View at Google Scholar · View at Scopus
  17. P. L. T. Boudreault, J. F. Morin, and M. Leclerc, “Synthesis of poly(2,7-carbazole)s and derivatives,” in Design and Synthesis of Conjugated Polymers, pp. 205–226, 2010. View at Google Scholar
  18. S.-I. Kato, H. Noguchi, A. Kobayashi, T. Yoshihara, S. Tobita, and Y. Nakamura, “Bicarbazoles: systematic structure-property investigations on a series of conjugated carbazole dimers,” Journal of Organic Chemistry, vol. 77, no. 20, pp. 9120–9133, 2012. View at Publisher · View at Google Scholar · View at Scopus
  19. A. Mishra, C.-Q. Ma, and P. Bäuerle, “Functional oligothiophenes: molecular design for multidimensional nanoarchitectures and their applications,” Chemical Reviews, vol. 109, no. 3, pp. 1141–1176, 2009. View at Publisher · View at Google Scholar · View at Scopus
  20. I. F. Perepichka and D. F. Perepichka, Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics, Wiley Online Library, 2009.
  21. J.-F. Morin, N. Drolet, Y. Tao, and M. Leclerc, “Syntheses and characterization of electroactive and photoactive 2,7-carbazolenevinylene-based conjugated oligomers and polymers,” Chemistry of Materials, vol. 16, no. 23, pp. 4619–4626, 2004. View at Publisher · View at Google Scholar · View at Scopus
  22. M. Belletête, J.-F. Morin, M. Leclerc, and G. Durocher, “A theoretical, spectroscopic, and photophysical study of 2,7-carbazolenevinylene-based conjugated derivatives,” The Journal of Physical Chemistry A, vol. 109, no. 31, pp. 6953–6959, 2005. View at Publisher · View at Google Scholar · View at Scopus
  23. J. Lu, P. F. Xia, P. K. Lo, Y. Tao, and M. S. Wong, “Synthesis and properties of multi-triarylamme-substituted carbazole-based dendrimers with an oligothiophene core for potential applications in organic solar cells and light-emitting diodes,” Chemistry of Materials, vol. 18, no. 26, pp. 6194–6203, 2006. View at Publisher · View at Google Scholar · View at Scopus
  24. M. Melucci, L. Favaretto, C. Bettini et al., “Liquid-crystalline rigid-core semiconductor oligothiophenes: influence of molecular structure on phase behaviour and thin-film properties,” Chemistry—A European Journal, vol. 13, no. 36, pp. 10046–10054, 2007. View at Publisher · View at Google Scholar · View at Scopus
  25. T. Khanasa, N. Prachumrak, R. Rattanawan et al., “Bis(carbazol-9-ylphenyl) aniline end-capped oligoarylenes as solution-processed nondoped emitters for full-emission color tuning organic light-emitting diodes,” The Journal of Organic Chemistry, vol. 78, no. 13, pp. 6702–6713, 2013. View at Publisher · View at Google Scholar · View at Scopus
  26. N. Koumura, Z.-S. Wang, S. Mori, M. Miyashita, E. Suzuki, and K. Hara, “Alkyl-functionalized organic dyes for efficient molecular photovoltaics,” Journal of the American Chemical Society, vol. 128, no. 44, pp. 14256–14257, 2006. View at Publisher · View at Google Scholar · View at Scopus
  27. Z.-S. Wang, N. Koumura, Y. Cui et al., “Hexylthiophene-functionalized carbazole dyes for efficient molecular photovoltaics: tuning of solar-cell performance by structural modification,” Chemistry of Materials, vol. 20, no. 12, pp. 3993–4003, 2008. View at Publisher · View at Google Scholar · View at Scopus
  28. N. Koumura, Z.-S. Wang, M. Miyashita et al., “Substituted carbazole dyes for efficient molecular photovoltaics: long electron lifetime and high open circuit voltage performance,” Journal of Materials Chemistry, vol. 19, no. 27, pp. 4829–4836, 2009. View at Publisher · View at Google Scholar · View at Scopus
  29. Y. Ooyama, Y. Shimada, S. Inoue et al., “New molecular design of donor-π-acceptor dyes for dye-sensitized solar cells: control of molecular orientation and arrangement on TiO2 surface,” New Journal of Chemistry, vol. 35, no. 1, pp. 111–118, 2011. View at Publisher · View at Google Scholar · View at Scopus
  30. W. Lee, N. Cho, J. Kwon, J. Ko, and J.-I. Hong, “New organic dye based on a 3,6-disubstituted carbazole donor for efficient dye-sensitized solar cells,” Chemistry—An Asian Journal, vol. 7, no. 2, pp. 343–350, 2012. View at Publisher · View at Google Scholar · View at Scopus
  31. C. Chen, J.-Y. Liao, Z. Chi et al., “Metal-free organic dyes derived from triphenylethylene for dye-sensitized solar cells: tuning of the performance by phenothiazine and carbazole,” Journal of Materials Chemistry, vol. 22, no. 18, pp. 8994–9005, 2012. View at Publisher · View at Google Scholar · View at Scopus
  32. T. Sudyoadsuk, S. Pansay, S. Morada et al., “Synthesis and characterization of D–D–π–A-type organic dyes bearing carbazole-carbazole as a donor moiety (D–D) for efficient dye-sensitized solar cells,” European Journal of Organic Chemistry, vol. 2013, no. 23, pp. 5051–5063, 2013. View at Publisher · View at Google Scholar
  33. G. Wei, R. R. Lunt, K. Sun, S. Wang, M. E. Thompson, and S. R. Forrest, “Efficient, ordered bulk heterojunction nanocrystalline solar cells by annealing of ultrathin squaraine thin films,” Nano Letters, vol. 10, no. 9, pp. 3555–3559, 2010. View at Publisher · View at Google Scholar · View at Scopus
  34. V. Coropceanu, J. Cornil, D. A. da Silva Filho, Y. Olivier, R. Silbey, and J.-L. Brédas, “Charge transport in organic semiconductors,” Chemical Reviews, vol. 107, no. 4, pp. 926–952, 2007. View at Publisher · View at Google Scholar · View at Scopus
  35. B. Walker, A. B. Tamayo, X.-D. Dang et al., “Nanoscale phase separation and high photovoltaic efficiency in solution-processed, small-molecule bulk heterojunction solar cells,” Advanced Functional Materials, vol. 19, no. 19, pp. 3063–3069, 2009. View at Publisher · View at Google Scholar · View at Scopus
  36. B. Walker, C. Kim, and T.-Q. Nguyen, “Small molecule solution-processed bulk heterojunction solar cells,” Chemistry of Materials, vol. 23, no. 3, pp. 470–482, 2011. View at Publisher · View at Google Scholar · View at Scopus
  37. N. Miyaura and A. Suzuki, “Palladium-catalyzed cross-coupling reactions of organoboron compounds,” Chemical Reviews, vol. 95, no. 7, pp. 2457–2483, 1995. View at Publisher · View at Google Scholar · View at Scopus
  38. I. P. Beletskaya and A. V. Cheprakov, “Copper in cross-coupling reactions: the post-Ullmann chemistry,” Coordination Chemistry Reviews, vol. 248, no. 21–24, pp. 2337–2364, 2004. View at Publisher · View at Google Scholar · View at Scopus
  39. B. R. Kaafarani, A. O. El-Ballouli, R. Trattnig et al., “Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene: synthesis, structures, optical properties, electrochemistry, and electroluminescence,” Journal of Materials Chemistry C, vol. 1, no. 8, pp. 1638–1650, 2013. View at Publisher · View at Google Scholar · View at Scopus
  40. B. E. Koene, D. E. Loy, and M. E. Thompson, “Asymmetric triaryldiamines as thermally stable hole transporting layers for organic light-emitting devices,” Chemistry of Materials, vol. 10, no. 8, pp. 2235–2250, 1998. View at Publisher · View at Google Scholar · View at Scopus
  41. P. Schrögel, A. Tomkevičiene, P. Strohriegl, S. T. Hoffmann, A. Köhler, and C. Lennartz, “A series of CBP-derivatives as host materials for blue phosphorescent organic light-emitting diodes,” Journal of Materials Chemistry, vol. 21, no. 7, pp. 2266–2273, 2011. View at Publisher · View at Google Scholar · View at Scopus
  42. C. Chi and G. Wegner, “Chain-length dependence of the electrochemical properties of conjugated oligofluorenes,” Macromolecular Rapid Communications, vol. 26, no. 19, pp. 1532–1537, 2005. View at Publisher · View at Google Scholar · View at Scopus
  43. J. Pommerehne, H. Vestweber, W. Guss et al., “Efficient two layer LEDs on a polymer blend basis,” Advanced Materials, vol. 7, no. 6, pp. 551–554, 1995. View at Publisher · View at Google Scholar · View at Scopus
  44. K. Hara, K. Miyamoto, Y. Abe, and M. Yanagida, “Electron transport in coumarin-dye-sensitized nanocrystalline TiO2 electrodes,” The Journal of Physical Chemistry B, vol. 109, no. 50, pp. 23776–23778, 2005. View at Publisher · View at Google Scholar · View at Scopus
  45. H. Cao, J. Ma, G. Zhang, and Y. Jiang, “Borole/thiophene cooligomers and copolymers with quinoid structures and biradical characters,” Macromolecules, vol. 38, no. 4, pp. 1123–1130, 2005. View at Publisher · View at Google Scholar
  46. S. T. Hoffmann, P. Schrögel, M. Rothmann, R. Q. Albuquerque, P. Strohriegl, and A. Köhler, “Triplet excimer emission in a series of 4,4′-bis(N-carbazolyl)-2,2′-biphenyl derivatives,” The Journal of Physical Chemistry B, vol. 115, no. 3, pp. 414–421, 2011. View at Publisher · View at Google Scholar · View at Scopus
  47. M. Belletête, M. Bédard, M. Leclerc, and G. Durocher, “Ground and excited state properties of carbazole-based dyads: correlation with their respective absorption and fluorescence spectra,” Journal of Molecular Structure: THEOCHEM, vol. 679, no. 1-2, pp. 9–15, 2004. View at Publisher · View at Google Scholar · View at Scopus
  48. L. Yang, J.-K. Feng, A.-M. Ren, and J.-Z. Sun, “The electronic structure and optical properties of carbazole-based conjugated oligomers and polymers: a theoretical investigation,” Polymer, vol. 47, no. 4, pp. 1397–1404, 2006. View at Publisher · View at Google Scholar · View at Scopus
  49. K. R. Radke, K. Ogawa, and S. C. Rasmussen, “Highly fluorescent oligothiophenes through the incorporation of central dithieno[3, 2-b: 2′, 3′-d]pyrrole units,” Organic Letters, vol. 7, no. 23, pp. 5253–5256, 2005. View at Publisher · View at Google Scholar · View at Scopus
  50. I. B. Berlman, “Empirical correlation between nuclear conformation and certain fluorescence and absorption characteristics of aromatic compounds,” The Journal of Physical Chemistry, vol. 74, no. 16, pp. 3085–3093, 1970. View at Publisher · View at Google Scholar · View at Scopus
  51. S.-I. Kato, S. Shimizu, A. Kobayashi, T. Yoshihara, S. Tobita, and Y. Nakamura, “Systematic structure–property investigations on a series of alternating carbazole–thiophene oligomers,” The Journal of Organic Chemistry, vol. 79, no. 2, pp. 618–629, 2014. View at Publisher · View at Google Scholar · View at Scopus
  52. A. Hlel, A. Mabrouk, M. Chemek, I. Ben Khalifa, and K. Alimi, “A DFT study of charge-transfer and opto-electronic properties of some new materials involving carbazole units,” Computational Condensed Matter, vol. 3, pp. 30–40, 2015. View at Publisher · View at Google Scholar · View at Scopus
  53. X. Lu, S. Fan, J. Wu, X. Jia, Z.-S. Wang, and G. Zhou, “Controlling the charge transfer in D-A-D chromophores based on pyrazine derivatives,” The Journal of Organic Chemistry, vol. 79, no. 14, pp. 6480–6489, 2014. View at Publisher · View at Google Scholar · View at Scopus
  54. A. R. Murphy and J. M. J. Fréchet, “Organic semiconducting oligomers for use in thin film transistors,” Chemical Reviews, vol. 107, no. 4, pp. 1066–1096, 2007. View at Publisher · View at Google Scholar · View at Scopus
  55. S. Allard, M. Forster, B. Souharce, H. Thiem, and U. Scherf, “Organic semiconductors for solutionprocessable fieldeffect transistors (OFETs),” Angewandte Chemie—International Edition, vol. 47, no. 22, pp. 4070–4098, 2008. View at Google Scholar
  56. P. M. Beaujuge and J. M. J. Fréchet, “Molecular design and ordering effects in π-functional materials for transistor and solar cell applications,” Journal of the American Chemical Society, vol. 133, no. 50, pp. 20009–20029, 2011. View at Publisher · View at Google Scholar · View at Scopus
  57. N. Acar, J. Kurzawa, N. Fritz et al., “Phenothiazine—pyrene dyads: photoinduced charge separation and structural relaxation in the CT state,” Journal of Physical Chemistry A, vol. 107, no. 45, pp. 9530–9541, 2003. View at Publisher · View at Google Scholar · View at Scopus
  58. C. Lee, W. Yang, and R. G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Physical Review B, vol. 37, no. 2, pp. 785–789, 1988. View at Publisher · View at Google Scholar · View at Scopus
  59. S. Tretiak and S. Mukamel, “Density matrix analysis and simulation of electronic excitations in conjugated and aggregated molecules,” Chemical Reviews, vol. 102, no. 9, pp. 3171–3212, 2002. View at Publisher · View at Google Scholar · View at Scopus
  60. Y. Wu, H. Guo, T. D. James, and J. Zhao, “Enantioselective recognition of mandelic acid by a 3,6-dithiophen-2-yl-9H-carbazole-based chiral fluorescent bisboronic acid sensor,” The Journal of Organic Chemistry, vol. 76, no. 14, pp. 5685–5695, 2011. View at Publisher · View at Google Scholar · View at Scopus
  61. S. H. Tucker, “Iodination in the carbazole series,” Journal of the Chemical Society, vol. 1, pp. 548–553, 1926. View at Google Scholar
  62. 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, vol. 63, no. 9, pp. 1913–1922, 2007. View at Publisher · View at Google Scholar · View at Scopus