Synthesis of a disulfide functionalized diacetylenic derivative of carbazole as building-block of polymerizable self-assembled monolayers
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Sushilkumar Jadhav
und
Massimo Maccagno
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).
[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. http://dx.doi.org/10.1016/j.susc.2004.02.01110.1016/j.susc.2004.02.011Suche in Google 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. http://dx.doi.org/10.1021/jp064077710.1021/jp0640777Suche in Google 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. http://dx.doi.org/10.1021/ja00082a02810.1021/ja00082a028Suche in Google 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. http://dx.doi.org/10.1016/j.apsusc.2004.11.04510.1016/j.apsusc.2004.11.045Suche in Google 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. http://dx.doi.org/10.1126/science.834202110.1126/science.8342021Suche in Google Scholar PubMed
[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. http://dx.doi.org/10.1021/la051415710.1021/la0514157Suche in Google Scholar PubMed
[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. http://dx.doi.org/10.1039/c2jm14239b10.1039/c2jm14239bSuche in Google 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. http://dx.doi.org/10.2478/s11532-011-0140-510.2478/s11532-011-0140-5Suche in Google 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. http://dx.doi.org/10.1021/jo902454510.1021/jo9024545Suche in Google Scholar PubMed
[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. http://dx.doi.org/10.1021/ja00119a01010.1021/ja00119a010Suche in Google 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. http://dx.doi.org/10.1021/jo301701a10.1021/jo301701aSuche in Google 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. http://dx.doi.org/10.1021/nn103231j10.1021/nn103231jSuche in Google 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. http://dx.doi.org/10.1016/S0032-3861(00)00148-810.1016/S0032-3861(00)00148-8Suche in Google 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. 10.1021/la00058a060Suche in 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. http://dx.doi.org/10.1021/la00038a04710.1021/la00038a047Suche in Google 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. http://dx.doi.org/10.1103/PhysRevB.33.438610.1103/PhysRevB.33.4386Suche in Google Scholar PubMed
[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. http://dx.doi.org/10.1021/ja111673x10.1021/ja111673xSuche in Google Scholar PubMed
[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. http://dx.doi.org/10.1039/c2nr30245d10.1039/c2nr30245dSuche in Google Scholar PubMed
[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. http://dx.doi.org/10.1021/jo701918z10.1021/jo701918zSuche in Google Scholar PubMed
[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. http://dx.doi.org/10.1021/cr050258d10.1021/cr050258dSuche in Google Scholar PubMed
[21] Ulman, A. (1991). An introduction to ultrathin organic films. New York, NY, USA: Academic Press. Suche in 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. http://dx.doi.org/10.1021/ja00198a02010.1021/ja00198a020Suche in Google 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. http://dx.doi.org/10.2478/s11696-012-0147-110.2478/s11696-012-0147-1Suche in Google Scholar
© 2013 Institute of Chemistry, Slovak Academy of Sciences
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- Synthesis of ethyl-6-aminohexanoate from caprolactam and ethanol in near-critical water
- Vanadium dodecylamino phosphate: A novel efficient catalyst for synthesis of polyhydroquinolines
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