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).
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Tao, F., & Bernasek, S. L. (2007). Understanding odd-even effects in organic self-assembled monolayers. Chemical Reviews, 107, 1408–1453. DOI: 10.1021/cr050258d.
Ulman, A. (1991). An introduction to ultrathin organic films. New York, NY, USA: Academic Press.
Wenzel, M., & Atkinson, G. H. (1989). Chromatic properties of polydiacetylene films. Journal of the American Chemical Society, 111, 6123–6127. DOI: 10.1021/ja00198a020.
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.
Author information
Authors and Affiliations
Rights 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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11696-013-0437-2