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Journal of Nanomaterials
Volume 2013 (2013), Article ID 368202, 8 pages
http://dx.doi.org/10.1155/2013/368202
Research Article

Diarylfluorene-Based Shape-Persistent Organic Nanomolecular Frameworks via Iterative Friedel-Crafts Protocol toward Multicomponent Organic Semiconductors

1Center for Molecular Systems and Organic Devices (CMSOD), Key Laboratory for Organic Electronics and Information Displays (KLOEID) and Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications (NUPT), Nanjing 210046, China
2Jiangsu-Singapore Joint Research Center for Organic/Bio-Electronics and Information Displays and Institute of Advanced Materials, Nanjing University of Technology, Nanjing 211816, China

Received 4 January 2013; Accepted 11 February 2013

Academic Editor: Hongmei Luo

Copyright © 2013 Guang-Wei Zhang 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. L. H. Xie, C. R. Yin, W. Y. Lai, Q. L. Fan, and W. Huang, “Polyfluorene-based semiconductors combined with various periodic table elements for organic electronics,” Progress in Polymer Science, vol. 37, no. 9, pp. 1192–1264, 2012.
  2. L. H. Xie, Y. Z. Chang, J. F. Gu et al., “Design of organic/polymeric π-semiconductors: the four-element principle,” Acta Physico-Chimica Sinica, vol. 26, no. 7, pp. 1784–1794, 2010.
  3. L. H. Xie, W. Huang, and IEEE, “Bandgaps enigeering in light-emitting polymers via from p–n diblock compolymerization to inorganic/organic hybridization,” in 14th OptoElectronics and Communications Conference (OECC '09), pp. 492–493, July 2009.
  4. J. F. Pan, S. J. Chua, and W. Huang, “Tuning redox behavior and emissive wavelength of conjugated polymers by p–n diblock structures—a theoretical investigation,” Synthetic Metals, vol. 110, no. 1, pp. 85–89, 2000.
  5. W. Huang, H. Meng, W. L. Yu, J. Pei, Z. K. Chen, and Y. H. Lai, “A novel series of p–n diblock light-emitting copolymers based on oligothiophenes and 1,4-Bis(oxadiazolyl)-2,5-dialkyloxybenzene,” Macromolecules, vol. 32, no. 1, pp. 118–126, 1999. View at Scopus
  6. J. Liu, Q. G. Zhou, Y. X. Cheng et al., “The first single polymer with simultaneous blue, green, and red emission for white electroluminescence,” Advanced Materials, vol. 17, no. 24, pp. 2974–2978, 2005.
  7. J. Liu, L. Chen, S. Shao et al., “Three-color white electroluminescence from a single polymer system with blue, green and red dopant units as individual emissive species and polyfluorene as individual polymer host,” Advanced Materials, vol. 19, no. 23, pp. 4224–4228, 2007. View at Publisher · View at Google Scholar · View at Scopus
  8. Z. Zhang, Q. Wang, Y. Dai, Y. Liu, L. Wang, and D. Ma, “High efficiency fluorescent white organic light-emitting diodes with red, green and blue separately monochromatic emission layers,” Organic Electronics, vol. 10, no. 3, pp. 491–495, 2009.
  9. D. Venkataraman, S. Yurt, B. H. Venkatraman, and N. Gavvalapalli, “Role of molecular architecture in organic photovoltaic cells,” Journal of Physical Chemistry Letters, vol. 1, no. 6, pp. 947–958, 2010. View at Publisher · View at Google Scholar · View at Scopus
  10. J. Weickert, R. B. Dunbar, H. C. Hesse, W. Wiedemann, and L. Schmidt-Mende, “Nanostructured organic and hybrid solar cells,” Advanced Materials, vol. 23, no. 16, pp. 1810–1828, 2011.
  11. M. D. Allendorf, A. Schwartzberg, V. Stavila, and A. A. Talin, “A roadmap to implementing metal-organic frameworks in electronic devices: challenges and critical directions,” Chemistry, vol. 17, no. 41, pp. 11372–11388, 2011.
  12. A. P. Côté, A. I. Benin, N. W. Ockwig, M. O'Keeffe, A. J. Matzger, and O. M. Yaghi, “Chemistry: porous, crystalline, covalent organic frameworks,” Science, vol. 310, no. 5751, pp. 1166–1170, 2005. View at Publisher · View at Google Scholar · View at Scopus
  13. H. M. El-Kaderi, J. R. Hunt, J. L. Mendoza-Cortes et al., “Designed synthesis of 3D covalent organic frameworks,” Science, vol. 316, no. 5822, pp. 268–272, 2007.
  14. M. Eddaoudi, J. Kim, J. B. Wachter, H. K. Chae, M. O'Keeffe, and O. M. Yaghi, “Porous metal-organic polyhedra: 25 Å cuboctahedron constructed from 12 Cu2(CO2)4 paddle-wheel building blocks,” Journal of the American Chemical Society, vol. 123, no. 18, pp. 4368–4369, 2001. View at Publisher · View at Google Scholar · View at Scopus
  15. J. J. I. V. Perry, J. A. Perman, and M. J. Zaworotko, “Design and synthesis of metal-organic frameworks using metal-organic polyhedra as supermolecular building blocks,” Chemical Society Reviews, vol. 38, no. 5, pp. 1400–1417, 2009.
  16. D. J. L. Tranchemontagne, Z. Ni, M. O'Keeffe, and O. M. Yaghi, “Reticular chemistry of metal-organic polyhedra,” Angewandte Chemie, vol. 47, no. 28, pp. 5136–5147, 2008.
  17. J. Lohrman, C. Zhang, W. Zhang, and S. Ren, “Semiconducting carbon nanotube and covalent organic polyhedron-C-60 nanohybrids for light harvesting,” Chemical Communications, vol. 48, no. 6717, pp. 8377–8379, 2012.
  18. Y. Jin, A. Jin, R. McCaffrey, H. Long, and W. Zhang, “Design strategies for shape-persistent covalent organic polyhedrons (COPs) through imine condensation/metathesis,” Journal of Organic Chemistry, vol. 77, no. 17, pp. 7392–7400, 2012.
  19. L. H. Xie, X. Y. Hou, Y. R. Hua et al., “Facile synthesis of complicated 9, 9-diarylfluorenes based on BF3·Et2O-mediated Friedel-Crafts reaction,” Organic Letters, vol. 8, no. 177, pp. 3701–3704, 2006.
  20. L. H. Xie, X. Y. Hou, C. Tang et al., “Novel H-shaped persistent architecture based on a dispirlo building block system,” Organic Letters, vol. 8, no. 7, pp. 1363–1366, 2006.
  21. L. H. Xie, F. Liu, C. Tang et al., “Unexpected one-pot method to synthesize spiro[fluorene-9,9'-xanthene] building blocks for blue-light-emitting materials,” Organic Letters, vol. 8, no. 13, pp. 2787–2790, 2006. View at Publisher · View at Google Scholar · View at Scopus
  22. L. H. Xie, X. Y. Hou, Y. R. Hua et al., “Facile synthesis of complicated 9,9-diarylfluorenes based on BF3·Et2O-mediated Friedel-Crafts reaction,” Organic Letters, vol. 8, no. 17, pp. 3701–3704, 2006. View at Publisher · View at Google Scholar · View at Scopus
  23. L. H. Xie, Q. D. Ling, X. Y. Hou, and W. Huang, “An effective Friedel-Crafts postfunctionalization of poly(N-vinylcarbazole) to tune carrier transportation of supramolecular organic semiconductors based on π-stacked polymers for nonvolatile flash memory cell,” Journal of the American Chemical Society, vol. 130, no. 7, pp. 2120–2121, 2008. View at Publisher · View at Google Scholar · View at Scopus
  24. C. R. Yin, S. H. Ye, J. Zhao et al., “Hindrance-functionalized π-stacked polymer host materials of the Cardo-type carbazole-fluorene hybrid for solution-processable blue electrophosphorescent devices,” Macromolecules, vol. 44, no. 12, pp. 4589–4595, 2011.
  25. L. H. Xie, X. Y. U. Deng, L. Chen et al., “A π-stacked and conjugated hybrid based on poly(N-vinylcarbazole) postfunctionalized with terfluorene for stable deep-blue hole-transporting materials,” Journal of Polymer Science A, vol. 47, no. 20, pp. 5221–5229, 2009. View at Publisher · View at Google Scholar · View at Scopus
  26. Z. D. Liu, Y. Z. Chang, C. J. Ou et al., “BF3·Et2O-mediated Friedel-Crafts C–H bond polymerization to synthesize π-conjugation-interrupted polymer semiconductors,” Polymer Chemistry, vol. 2, no. 10, pp. 2179–2182, 2011.
  27. F. Liu, J. Q. Liu, R. R. Liu et al., “Hyperbranched framework of interrupted π-conjugated polymers end-capped with high carrier-mobility moieties for stable light-emitting materials with low driving voltage,” Journal of Polymer Science A, vol. 47, no. 23, pp. 6451–6462, 2009. View at Publisher · View at Google Scholar · View at Scopus
  28. B. Y. Ren, C. J. Ou, C. Zhang et al., “Diarylfluorene-modified fulleropyrrolidine acceptors to tune aggregate morphology for solution-processable polymer/fullerene bulk-heterojunction solar cells,” Journal of Physical Chemistry C, vol. 116, no. 16, pp. 8881–8887, 2012.