Skip to main content
SpringerLink
Log in

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

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

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).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • Tao, F., & Bernasek, S. L. (2007). Understanding odd-even effects in organic self-assembled monolayers. Chemical Reviews, 107, 1408–1453. DOI: 10.1021/cr050258d.

    Article  CAS  Google Scholar 

  • Ulman, A. (1991). An introduction to ultrathin organic films. New York, NY, USA: Academic Press.

    Google Scholar 

  • Wenzel, M., & Atkinson, G. H. (1989). Chromatic properties of polydiacetylene films. Journal of the American Chemical Society, 111, 6123–6127. DOI: 10.1021/ja00198a020.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Applied Science and Technology, Polytechnic University of Turin, 10129, Turin, Italy

    Sushilkumar A. Jadhav

  2. Department of Chemistry and Industrial Chemistry, University of Genoa, 16146, Genoa, Italy

    Sushilkumar A. Jadhav & Massimo Maccagno

Authors
  1. Sushilkumar A. Jadhav
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Massimo Maccagno
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jadhav, S.A., Maccagno, M. Synthesis of a disulfide functionalized diacetylenic derivative of carbazole as building-block of polymerizable self-assembled monolayers. Chem. Pap. 68, 239–245 (2014). https://doi.org/10.2478/s11696-013-0437-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11696-013-0437-2

Keywords

Search

Navigation