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Received November 14, 2005
Accepted December 19, 2005
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Synthesis of trans-substituted porphyrin building blocks containing two S-trityl or thiol groups
School of Chemical and Biological Engineering, Institute of Chemical Processes, Seoul National University, Seoul 151-742, Korea 1Department of Chemical Engineering, Kwangwoon University, Seoul 139-701, Korea
Korean Journal of Chemical Engineering, May 2006, 23(3), 512-515(4), 10.1007/BF02706758
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Abstract
The synthesis of some linear structured trans-porphyrin bearing functional groups (S-trityl or thiol) was described. The rational synthetic pathway consisted of 6 reaction steps (up to S-trityl derivatized porphyrin, 5 steps), constituting a MacDonald-type 2+2 condensation and amine-carboxylic acid coupling. The completion of each step was confirmed by 1H-NMR, UV/Vis adsorption, and FAM-MS. The resulting porphyrins would be applicable to the study of self-assembled gold-thiol structures, due to the reactive nature of the molecules with a gold surface.
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References
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Gulino A, Mineo P, Scamporrino E, Vitalini D, Fragala I, Chem. Mater., 16(10), 1838 (2004)
Holten D, Bocian DF, Lindsey JS, Accounts Chem. Res., 35, 57 (2002)
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Imahori H, Arimura M, Hanada T, Nishimura Y, Yamazaki I, Sakata Y, Fukuzumi S, J. Am. Chem. Soc., 123(2), 335 (2001)
Imahori H, Mori Y, Matano Y, J. Photochem. Photobiol. C, 4, 51 (2003)
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Laha JK, Dhanalekshmi S, Taniguchi M, Ambroise A, Lindsey JS, Org. Process Res., 7(6), 799 (2003)
Littler BJ, Ciringh Y, Lindsey JS, J. Org. Chem., 64(8), 2864 (1999)
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