Advertisement

Chemical Papers

, Volume 68, Issue 2, pp 239–245 | Cite as

Synthesis of a disulfide functionalized diacetylenic derivative of carbazole as building-block of polymerizable self-assembled monolayers

  • Sushilkumar A. Jadhav
  • Massimo Maccagno
Original Paper

Abstract

A new symmetrical disulfide containing a diacetylenic unit and bearing a fluorescent carbazolyl end-group forming polymerizable self-assembled monolayers on metallic nanostructures has been synthesized. Suitable modifications of the synthetic steps involved in the synthesis of such derivatives were made in order to assure better synthetic pathway. Conversion of the tosylated derivative into the final symmetrical disulfide is carried out using sodium hydrosulfide (NaSH).

Keywords

symmetrical disulfide diacetylene sodium hydrosulfide 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Alloisio, M., Sottini, S., Riello, P., Giorgetti, E., Margheri, G., Cuniberti, C., & Dellepiane, G. (2004). AFM, SEM and GIXRD studies of thin films of red polycarbazolyldlacetylenes. Surface Science, 554, 68–75. DOI: 10.1016/j. susc.2004.02.011.CrossRefGoogle Scholar
  2. Alloisio, M., Demartini, A., Cuniberti, C., Petrillo, G., Thea, S., Giorgetti, E., Giusti, A., & Dellepiane, G. (2007). Self-assembled monolayers of disulfide-functionalized diacetylenes on gold films and nanoparticles. Journal of Physical Chemistry C, 111, 345–353. DOI: 10.1021/jp0640777.CrossRefGoogle Scholar
  3. Batchelder, D. N., Evans, S. D., Freeman, T. L., Haeussling, L., Ringsdorf, H., & Wolf, H. (1994). Self-assembled monolayers containing polydiacetylenes. Journal of the American Chemical Society, 116, 1050–1053. DOI: 10.1021/ja00082a028.CrossRefGoogle Scholar
  4. Cavalleri, O., Prato, M., Chincarini, A., Rolandi, R., Canepa, M., Gliozzi, A., Alloisio, M., Lavagnino, L., Cuniberti, C., Dell’Erba, C., & Dellepiane, G. (2005). Self-assembled monolayers of a novel diacetylene on gold. Applied Surface Science, 246, 403–408. DOI: 10.1016/j.apsusc.2004.11.045.CrossRefGoogle Scholar
  5. Charyach, D. H., Nagy, J. O., Spevak, W., & Bedvarski, M. D. (1993). Direct colorimetric detection of a receptor-ligand interaction by a polymerized bilayer assembly. Science, 261, 585–588. DOI: 10.1126/science.8342021.CrossRefGoogle Scholar
  6. Giorgetti, E., Muniz-Miranda, M., Margheri, G., Giusti, A., Sottini, S., Alloisio, M., Cuniberti, C., & Dellepiane, G. (2006). UV polymerization of self-assembled monolayers of a novel diacetylene on silver: A spectroscopic analysis by surface plasmon resonance and surface enhanced Raman scattering. Langmuir, 22, 1129–1134. DOI: 10.1021/la0514157.CrossRefGoogle Scholar
  7. Jadhav, S. A. (2012a). Functional self-assembled monolayers (SAMs) of organic compounds on gold nanoparticles. Journal of Materials Chemistry, 22, 5894–5899. DOI: 10.1039/c2jm14239b.CrossRefGoogle Scholar
  8. Jadhav, S. A. (2012b). Synthesis of fluorescent long-chain thiols/disulfides as building-blocks for self-assembled monolayers preparation. Central European Journal of Chemistry, 10, 295–299. DOI: 10.2478/s11532-011-0140-5.CrossRefGoogle Scholar
  9. Joly, K. M., Mirri, G., Willener, Y., Horswell, S. L., Moody, C. J., & Tucker, J. H. R. (2010). Synthesis of an achiral isomer of lipoic acid as an anchor group for SAM formation on gold surfaces. Journal of Organic Chemistry, 75, 2395–2398. DOI: 10.1021/jo9024545.CrossRefGoogle Scholar
  10. Kim, T., Crooks, R. M., Tsen, M., & Sun, L. (1995). Polymeric self-assembled monolayers. 2. Synthesis and characterization of self-assembled polydiacetylene mono- and multilayers. Journal of the American Chemical Society, 117, 3963–3967. DOI: 10.1021/ja00119a010.CrossRefGoogle Scholar
  11. Kota, R., Samudrala, R., & Mattern, D. L. (2012). Synthesis of donor-σ-perylenebisimide-acceptor molecules having PEG swallowtails and sulfur anchors. Journal of Organic Chemistry, 77, 9641–9651. DOI: 10.1021/jo301701a.CrossRefGoogle Scholar
  12. Mandal, S. K., Okawa, Y., Hasegawa, T., & Aono, M. (2011). Rate-determining factors in the chain polymerization of molecules initiated by local single-molecule excitation, ACS Nano, 5, 2779–2786. DOI: 10.1021/nn103231j.CrossRefGoogle Scholar
  13. Menzel, H., Horstmann, S., Mowery, M. D., Cai, M., & Evans, C. E. (2000). Diacetylene polymerization in self-assembled monolayers: Influence of the odd/even nature of the methylene spacer. Polymer, 41, 8113–8119. DOI: 10.1016/s0032-3861(00)00148-8.CrossRefGoogle Scholar
  14. Mino, N., Tamura, H., & Ogawa, K. (1991). Analysis of color transitions and changes on Langmuir-Blodgett films of a polydiacetylene derivative. Langmuir, 7, 2326–2341. DOI: 10.1021/la00058a060.Google Scholar
  15. Mino, N., Tamura, H., & Ogawa, K. (1992). Photoreactivity of 10,12-pentacosadiynoic acid monolayers and color transitions of the polymerized monolayers on an aqueous subphase. Langmuir, 8, 594–598. DOI: 10.1021/la00038a047.CrossRefGoogle Scholar
  16. Miyano, K., & Maeda, T. (1986). Photoluminescence, absorption, and Raman spectra of a polydiacetylene monolayer. Physical Review B, 33, 4386–4388. DOI: 10.1103/physrevb.33.4386.CrossRefGoogle Scholar
  17. Okawa, Y., Mandal, S. K., Hu, C. P., Tateyama, Y., Goedecker, S., Tsukamoto, S., Hasegawa, T., Gimzewski, J. K., & Aono, M. (2011). Chemical wiring and soldering toward all-molecule electronic circuitry. Journal of the American Chemical Society, 133, 8227–8233. DOI: 10.1021/ja111673x.CrossRefGoogle Scholar
  18. Okawa, Y., Akai-Kasaya, M., Kuwahara, Y., Mandal, S. K., & Aono, M. (2012). Controlled chain polymerisation and chemical soldering for single-molecule electronics. Nanoscale, 4, 3013–3028. DOI: 10.1039/c2nr30245d.CrossRefGoogle Scholar
  19. Operamolla, A., Omar, O. H., Babudri, F., Farinola, G. M., & Naso, F. (2007). Synthesis of S-acetyl oligoarylenedithiols via Suzuki-Miyaura cross-coupling. Journal of Organic Chemistry, 72, 10272–10275. DOI: 10.1021/jo701918z.CrossRefGoogle Scholar
  20. Tao, F., & Bernasek, S. L. (2007). Understanding odd-even effects in organic self-assembled monolayers. Chemical Reviews, 107, 1408–1453. DOI: 10.1021/cr050258d.CrossRefGoogle Scholar
  21. Ulman, A. (1991). An introduction to ultrathin organic films. New York, NY, USA: Academic Press.Google Scholar
  22. Wenzel, M., & Atkinson, G. H. (1989). Chromatic properties of polydiacetylene films. Journal of the American Chemical Society, 111, 6123–6127. DOI: 10.1021/ja00198a020.CrossRefGoogle Scholar
  23. Zhao, C., Li, L. Y., Guo, M. M., & Zheng, J. (2012). Functional polymer thin films designed for antifouling materials and biosensors. Chemical Papers, 66, 323–339. DOI: 10.2478/s11696-012-0147-1.CrossRefGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2013

Authors and Affiliations

  • Sushilkumar A. Jadhav
    • 1
    • 2
  • Massimo Maccagno
    • 2
  1. 1.Department of Applied Science and TechnologyPolytechnic University of TurinTurinItaly
  2. 2.Department of Chemistry and Industrial ChemistryUniversity of GenoaGenoaItaly

Personalised recommendations