About this Journal Submit a Manuscript Table of Contents
Journal of Nanomaterials
Volume 2013 (2013), Article ID 624927, 7 pages
http://dx.doi.org/10.1155/2013/624927
Research Article

Solvent-Dependent Self-Assembly of 4,7-Dibromo-5,6-bis(octyloxy)benzo[c][1,2,5] Thiadiazole on Graphite Surface by Scanning Tunneling Microscopy

College of Materials Science and Engineering, South China University of Technology, Wushan Road, Tianhe District, Guangzhou, Guandgdong 510640, China

Received 9 May 2013; Revised 6 June 2013; Accepted 8 June 2013

Academic Editor: Amir Kajbafvala

Copyright © 2013 Bao Zha 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. S. Yagai, Y. Nakano, S. Seki et al., “Supramolecularly engineered aggregation of a dipolar dye: vesicular and ribbonlike architectures,” Angewandte Chemie—International Edition, vol. 49, no. 51, pp. 9990–9994, 2010. View at Publisher · View at Google Scholar · View at Scopus
  2. S. Lei, J. Puigmartí-Luis, A. Minoia et al., “Bottom-up assembly of high density molecular nanowire cross junctions at a solid/liquid interface,” Chemical Communications, no. 6, pp. 703–705, 2008. View at Publisher · View at Google Scholar · View at Scopus
  3. S.-L. Lee, N.-T. Lin, W.-C. Liao, C.-H. Chen, H.-C. Yang, and T.-Y. Luh, “Oligomeric tectonics: supramolecular assembly of double-stranded oligobisnorbornene through π-π stacking,” Chemistry—A European Journal, vol. 15, no. 43, pp. 11594–11600, 2009. View at Publisher · View at Google Scholar · View at Scopus
  4. J. A. A. W. Elemans, S. Lei, and S. de Feyter, “Molecular and supramolecular networks on surfaces: from two-dimensional crystal engineering to reactivity,” Angewandte Chemie—International Edition, vol. 48, no. 40, pp. 7298–7333, 2009. View at Publisher · View at Google Scholar · View at Scopus
  5. R. Otero, J. M. Gallego, A. L. V. de Parga, N. Martín, and R. Miranda, “Molecular self-assembly at solid surfaces,” Advanced Materials, vol. 23, no. 44, pp. 5148–5176, 2011. View at Publisher · View at Google Scholar · View at Scopus
  6. A. F. McGuire, A. D. Jewell, T. J. Lawton, C. J. Murphy, E. A. Lewis, and E. C. H. Sykes, “Hydrogen bonding and chirality in functionalized thioether self-assembly,” The Journal of Physical Chemistry C, vol. 116, no. 28, pp. 14992–14997, 2012. View at Publisher · View at Google Scholar
  7. A. Ciesielski, S. Lena, S. Masiero, G. P. Spada, and P. Samorì, “Dynamers at the solid-liquid interface: controlling the reversible assembly/reassembly process between two highly ordered supramolecular guanine motifs,” Angewandte Chemie—International Edition, vol. 49, no. 11, pp. 1963–1966, 2010. View at Publisher · View at Google Scholar · View at Scopus
  8. L. Xu, X. R. Miao, B. Zha, and W. L. Deng, “Self-assembly polymorphism: solvent-responsive two-dimensional morphologies of 2, 7-ditridecyloxy-9-fluorenone by scanning tunneling microscopy,” The Journal of Physical Chemistry C, vol. 116, pp. 16014–16022, 2012.
  9. L. Xu, X. R. Miao, B. Zha, and W. L. Deng, “Hydrogen-bonding-induced polymorphous phase transitions in 2D organic nanostructures,” Chemistry—An Asian Journal, vol. 8, pp. 926–933, 2013.
  10. Y. Miyake, T. Nagata, H. Tanaka et al., “Entropy-controlled 2D supramolecular structures of N, N′-bis(n-alkyl)naphthalenediimides on a HOPG surface,” Acs Nano, vol. 6, no. 5, pp. 3867–3887, 2012. View at Publisher · View at Google Scholar
  11. Y. Yang, X. R. Miao, G. Liu, L. Xu, T. T. Wu, and W. L. Deng, “Self-assembly of dendronized non-planar conjugated molecules on a HOPG surface,” Applied Surface Science, vol. 263, pp. 73–78, 2012.
  12. S. S. Jester, E. Sigmund, L. M. Röck, and S. Höger, “Hierarchical self-assembly of polycyclic heteroaromatic stars into snowflake patterns,” Angewandte Chemie—International Edition, vol. 51, pp. 8555–8559, 2012.
  13. L. Xu, X. R. Miao, X. Ying, and W. L. Deng, “Two-dimensional self-assembled molecular structures formed by the competition of van der Waals forces and dipole-dipole interactions,” The Journal of Physical Chemistry C, vol. 116, no. 1, pp. 1061–1069, 2012. View at Publisher · View at Google Scholar · View at Scopus
  14. Y. J. Li, X. R. Miao, G. Liu, Z. M. Li, L. Xu, and W. L. Deng, “Effect of bromine and substituted alkyl chain on the interfacial self-assembly of bromobenzene derivatives by scanning tunneling microscopy,” Journal of Nanoscience and Nanotechnology, vol. 12, pp. 179–186, 2012. View at Publisher · View at Google Scholar
  15. J. K. Yoon, W.-J. Son, K.-H. Chung, H. Kim, S. Han, and S.-J. Kahng, “Visualizing halogen bonds in planar supramolecular systems,” The Journal of Physical Chemistry C, vol. 115, no. 5, pp. 2297–2301, 2011. View at Publisher · View at Google Scholar · View at Scopus
  16. J. Lieffrig, O. Jeannin, and M. Fourmigué, “Expanded halogen-bonded anion organic networks with star-shaped iodoethynyl-substituted molecules: from corrugated 2D hexagonal lattices to pyrite-type 2-fold interpenetrated Cubic lattices,” Journal of the American Chemical Society, vol. 135, no. 16, pp. 6200–6210, 2013. View at Publisher · View at Google Scholar
  17. X. R. Miao, L. Xu, Z. M. Li, and W. L. Deng, “Solvent-induced structural transitions of a 1,3,5-tris(10- ethoxycarbonyldecyloxy)benzene assembly revealed by scanning tunneling microscopy,” The Journal of Physical Chemistry C, vol. 115, no. 8, pp. 3358–3367, 2011. View at Publisher · View at Google Scholar · View at Scopus
  18. X. Zhang, T. Chen, Q. Chen, G.-J. Deng, Q.-H. Fan, and L.-J. Wan, “One solvent induces a series of structural transitions in monodendron molecular self-assembly from lamellar to quadrangular to hexagonal,” Chemistry—A European Journal, vol. 15, no. 38, pp. 9669–9673, 2009. View at Publisher · View at Google Scholar · View at Scopus
  19. X. Zhang, Q. Chen, G.-J. Deng, Q.-H. Fan, and L.-J. Wan, “Structural diversity of a monodendron molecule self-assembly in different solvents investigated by scanning tunneling microscopy: from dispersant to counterpart,” The Journal of Physical Chemistry C, vol. 113, no. 36, pp. 16193–16198, 2009. View at Publisher · View at Google Scholar · View at Scopus
  20. W. Mamdouh, H. Uji-i, J. S. Ladislaw et al., “Solvent controlled self-assembly at the liquid-solid interface revealed by STM,” Journal of the American Chemical Society, vol. 128, no. 1, pp. 317–325, 2006. View at Publisher · View at Google Scholar · View at Scopus
  21. J. Kim, S. H. Park, S. Cho et al., “Low-bandgap poly(4H-cyclopenta[def]phenanthrene) derivatives with 4,7-dithienyl-2,1,3-benzothiadiazole unit for photovoltaic cells,” Polymer, vol. 51, no. 2, pp. 390–396, 2010. View at Publisher · View at Google Scholar · View at Scopus
  22. J. Bouffard and T. M. Swager, “Fluorescent conjugated polymers that incorporate substituted 2,1,3-benzooxadiazole and 2,1,3-benzothiadiazole units,” Macromolecules, vol. 41, no. 15, pp. 5559–5562, 2008. View at Publisher · View at Google Scholar · View at Scopus
  23. L. Huo, Y. Huang, B. Fan et al., “Synthesis of a 4,8-dialkoxy-benzo[1,2-b:4,5-b′]difuran unit and its application in photovoltaic polymer,” Chemical Communications, vol. 48, no. 27, pp. 3318–3320, 2012. View at Publisher · View at Google Scholar · View at Scopus
  24. Q. Hou, Q. Zhou, Y. Zhang, W. Yang, R. Yang, and Y. Cao, “Synthesis and electroluminescent properties of high-efficiency saturated red emitter based on copolymers from fluorene and 4,7-di(4-hexylthien-2-yl)-2,1, 3-benzothiadiazole,” Macromolecules, vol. 37, no. 17, pp. 6299–6305, 2004. View at Publisher · View at Google Scholar · View at Scopus
  25. P. Ding, C.-C. Chu, Y. Zou, D. Xiao, C. Pan, and C.-S. Hsu, “New low bandgap conjugated polymer derived from 2, 7-carbazole and 5, 6-bis(octyloxy)-4, 7-di(thiophen-2-yl) benzothiadiazole: synthesis and photovoltaic properties,” Journal of Applied Polymer Science, vol. 123, no. 1, pp. 99–107, 2012. View at Publisher · View at Google Scholar · View at Scopus
  26. R. Gutzler, C. Fu, A. Dadvand et al., “Halogen bonds in 2D supramolecular self-assembly of organic semiconductors,” Nanoscale, vol. 4, no. 19, pp. 5965–5971, 2012. View at Publisher · View at Google Scholar
  27. Q. Chen, T. Chen, D. Wang, H.-B. Liu, Y.-L. Li, and L.-J. Wan, “Structure and structural transition of chiral domains in oligo(p-phenylenevinylene) assembly investigated by scanning tunneling microscopy,” Proceedings of the National Academy of Sciences of the United States of America, vol. 107, no. 7, pp. 2769–2774, 2010. View at Publisher · View at Google Scholar · View at Scopus
  28. T. Chen, D. Wang, X. Zhang, Q.-L. Zhou, R.-B. Zhang, and L.-J. Wan, “In situ scanning tunneling microscopy of solvent-dependent chiral patterns of 1,4-di[4-N-(trihydroxymethyl)methyl carbamoylphenyl]-2,5-didodecyloxybenzene molecular assembly at a liquid/highly oriented pyrolytic graphite interface,” The Journal of Physical Chemistry C, vol. 114, no. 1, pp. 533–538, 2010. View at Publisher · View at Google Scholar · View at Scopus