Issue
Korean Journal of Chemical Engineering,
Vol.23, No.3, 512-515, 2006
Synthesis of trans-substituted porphyrin building blocks containing two S-trityl or thiol groups
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.
[References]
  1. Brust M, Bethell D, Kiely CJ, Schiffrin DJ, Langmuir, 14(19), 5425, 1998
  2. Cui XD, Primak A, Zarate X, Tomfohr J, Sankey OF, Moore AL, Moore TA, Gust D, Harris G, Lindsay SM, Science, 294, 571, 2001
  3. Gulino A, Mineo P, Scamporrino E, Vitalini D, Fragala I, Chem. Mater., 16(10), 1838, 2004
  4. Holten D, Bocian DF, Lindsey JS, Accounts Chem. Res., 35, 57, 2002
  5. Im SW, Yu BS, Hong SI, Korean J. Chem. Eng., 10(4), 207, 1993
  6. Imahori H, Arimura M, Hanada T, Nishimura Y, Yamazaki I, Sakata Y, Fukuzumi S, J. Am. Chem. Soc., 123(2), 335, 2001
  7. Imahori H, Mori Y, Matano Y, J. Photochem. Photobiol. C, 4, 51, 2003
  8. Inman CE, Reed SM, Hutchison JE, Langmuir, 20(21), 9144, 2004
  9. Laha JK, Dhanalekshmi S, Taniguchi M, Ambroise A, Lindsey JS, Org. Process Res., 7(6), 799, 2003
  10. Littler BJ, Ciringh Y, Lindsey JS, J. Org. Chem., 64(8), 2864, 1999
  11. Muthukumaran K, Loewe RS, Ambroise A, Tamaru Si, Li Q, Mathur G, Bocian DF, Misra V, Lindsey JS, J. Org. Chem., 69(5), 1444, 2004
  12. Steinbergyfrach G, Liddell PA, Hung SC, Moore AL, Gust D, Moore TA, Nature, 385(6613), 239, 1997
  13. Yamada H, Imahori H, Nishimura Y, Yamazaki I, Ahn TK, Kim SK, Kim D, Fukuzumi S, J. Am. Chem. Soc., 125(30), 9129, 2003