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BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access January 29, 2012

Synthesis of fluorescent long-chain thiols/disulfides as building-blocks for self-assembled monolayers preparation

Sushilkumar Jadhav EMAIL logo
From the journal Open Chemistry


New symmetrical disulfides together with the corresponding thiols bearing fluorescent end-groups have been synthesized as building-blocks for self-assembled monolayers (SAMs). The synthesis has been accomplished starting from aromatic nitrogen heterocycles in three steps. The conversion of the tosylated intermediate into the final disulfide is accomplished by use of sodium hydrogen sulfide (NaSH). Both products (thiols and disulfides) were isolated and characterized.

[1] A. Ulman, Chem. Rev. 96, 1533 (1996) in Google Scholar

[2] A. Ulman, An Introduction to Ultrathin Organic Films (Academic Press, New York, 1991) Search in Google Scholar

[3] J.C. Love, L.A. Estroff, J.K. Kriebel, R.G. Nuzzo, G.M. Whitesides, Chem. Rev. 105, 1103 (2005) in Google Scholar

[4] C.D. Bain, J. Evall, G.M. Whitesides, J. Am. Chem. Soc. 111, 7155 (1989) in Google Scholar

[5] C.D. Bain, G.M. Whitesides, Science (Washington, D.C.) 240, 62 (1988) in Google Scholar

[6] D. Witt, R. Klajn, P. Barski1, B.A. Grzybowski, Curr. Org. Chem. 8, 1763 (2004) and references therein in Google Scholar

[7] A. Operamolla, O. Hassan, F. Babudri, G.M. Farinola, F. Naso, J. Org. Chem. 72, 10272 (2007) in Google Scholar

[8] C.A. Canaria, J.O. Smith, C.J. Yu, S. E. Fraser, S. Lansford, Tetrahedron Lett. 46, 4813 (2005) in Google Scholar

[9] L.J. Yeager, Y.D. Amirsakis, E. Newman, R.L: Garrell, Tetrahedron Lett. 39, 8409 (1998) in Google Scholar

[10] F. Tao, S.L. Bernasek, Chem. Rev. 107, 1408 (2007) in Google Scholar PubMed

[11] R.J. Willicut, R.L. McCarley, Adv. Mater. 7, 759 (1995) in Google Scholar

[12] R.J. Willicut, R.L. McCarley, J. Am. Chem. Soc. 116, 10823 (1994) in Google Scholar

[13] J.M. Tour, Acc. Chem. Res. 33, 791 (2000) in Google Scholar PubMed

[14] R.W. Zehner, B.F. Parsons, R. P. Hsung, L.R. Sita, Langmuir 15, 1121 (1999) in Google Scholar

[15] T. Baunach, D.M. Kolb, Anal. Bioanal. Chem. 373, 74 (2002) 10.1007/s00216-002-1279-xSearch in Google Scholar PubMed

[16] J.L.G. Ruano, A. Parra, J. Aleman, J. Green Chem. 10, 706 (2008) in Google Scholar

[17] A. Ghorbani-Choghamarani, S.J. Sardari, J. of Sulfur Chem. 32, 63 (2011) in Google Scholar

Published Online: 2012-1-29
Published in Print: 2012-4-1

© 2012 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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