Supramolecular chirality control by solvent changes. Solvodichroic effect on chiral porphyrin aggregation

Chemical Communications

Volumn , Issue 19, 2005, Pages 2471-2473

  Monti, Donato ^a   Venanzi, Mariano ^a   Mancini, Giovanna ^b   Di Natale, Corrado ^a   Paolesse, Roberto ^a  

^a UNIVERSITY OF ROME TOR VERGATA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CHIRALITY; SUPRAMOLECULAR CHEMISTRY;

EID: 20044386130     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b419275c     Document Type: Article

References (26)

1. For a general overview, see: M. A. Matheos-Timoneda, M. Crego-Calama and D. N. Reinhoudt, Chem. Soc. Rev., 2004, 33, 363.
2. (a) R. F. Pasternack, C. Fleming, S. Herring, P. J. Collings, J. dePaula, G. DeCastro and E. J. Gibbs, Biophys. J., 2000, 79, 550;
3. (b) R. F. Pasternack, E. J. Gibbs, D. Bruzewicz, D. Stewart and K. S. Engstrom, J. Am. Chem. Soc., 2002, 124, 3533;
4. (c) R. F. Pasternack, E. J. Gibbs, P. J. Collings, J. C. dePaula, L. C. Turzo and A. Terracina, J. Am. Chem. Soc., 1998, 120, 5873;
5. (d) R. Lauceri, A. Raudino, L. Monsù Scolaro, N. Micali and R. Purrello, J. Am. Chem. Soc., 2002, 124, 894;
6. (e) R. Rubires, J.-A. Farrera and J. M. Ribó, Chem. Eur. J., 2001, 7, 436.
7. Cytochrome P-450: Structure, Mechanism and Biochemistry, ed. P. R. Ortiz de Montellano, 2nd edn., 1995, Plenum, New York.
8. T. S. Balaban, A. D. Bhise, M. Fisher, M. Linke-Schaetzel, C. Roussel and N. Vanthuyne, Angew. Chem. Int. Ed., 2003, 42, 2140.
9. (a) D. Monti, P. Tagliatesta, G. Mancini and T. Boschi, Angew. Chem. Int. Ed, 1998, 37, 1131;
10. (b) S. Borocci, F. Marotti, G. Mancini, D. Monti and A. Pastorini, Langmuir, 2001, 17, 7198;
11. (c) D. Monti, M. Venanzi, V. Cantonetti, S. Borocci and G. Mancini, Chem. Commun., 2002, 774;
12. (d) D. Monti, V. Cantonetti, M. Venanzi, F. Ceccacci, C. Bombelli and G. Mancini, Chem. Commun., 2004, 972;
13. (e) V. Cantonetti, D. Monti, M. Venanzi, C. Bombelli, F. Ceccacci and G. Mancini, Tetrahedron: Asymmetry, 2004, 15, 1969.
14. D. Monti, M. Venanzi, M. Russo, G. Bussetti, C. Goletti, M. Montalti, N. Zaccheroni, L. Prodi, R. Rella, M. G. Manera, C. Di Natale and R. Paolesse, New J. Chem., 2004, 28, 1123.
15. R. Paolesse, D. Monti, L. La Monica, M. Venanzi, A. Froiio, S. Nardis, C. Di Natale. E. Martinelli and A. D'Amico. Chem. Eur. J., 2002, 8, 2476.
16. M. Parschau, S. Romer, K.-H. Ernst and A. D. Schwab, J. Am. Chem. Soc., 2004, 126, 15398;
17. D. E. Smith, B. Bond-Watts, D. E. Johnston, J. Hone, A. T. Johnson, J. C. de Paula and W. F. Smith, Nano Lett., 2004, 1261;
18. C. F. van Nostrum and R. J. M. Nolte, Chem. Commun., 1996, 2385;
19. R. Yerushalmi, A. Scherz and E. van der Boom, J. Am. Chem. Soc., 2004, 126, 2700;
20. I. Goldberg, Chem. Commun., 2005, 1243.
21. The solvent effect (up to 45%) in chirogenesis in bis(porphyrin)-based systems has been recently reviewed: V. V. Borovkov, G. A. Hembury and Y. Inoue, Acc. Chem. Res., 2004, 37, 449.
22. For a very recent report on the effect of solvent on the aggregation behaviour of porphyrin derivatives, see: F. I. Simplicio, R. R. da Silva Soares, F. Maionchi, O. Santin Filho and N. Hioka, J. Phys. Chem. A., 2004, 108, 9384.
23. N. Micali, F. Mallamace, M. Castriciano, A. Romeo and L. Monsú Scolaro, Anal. Chem., 2001, 73, 4958.
24. J. M. Ribo, J. M. Bofill, J. Crusats and R. Rubires, Chem. Eur. J., 2001, 7, 2733.
25. R. F. Pasternack and P. J. Collings, Science, 1995, 269, 935.
26. J. C. Ma and D. A. Daugherty, Chem. Rev., 1997, 97, 1303.