Abstract
Molecular clips and tweezers tend to bind selectively electron deficient aromatic and aliphatic substrates. These interesting processes of molecular recognition are usually investigated in dilute solutions of organic or aqueous solvents. Due to discrepancy between polar and hydrophobic groups, molecular clips and tweezers are surface-active chemical compounds which can form monomolecular films at the surface of water. In this publication, we have systematically investigated the self-association and phase-behavior of these artificial receptors by means of pressure-area-isotherms and Brewster-Angle-Microscopy (BAM). We observed spherical and rod-shaped two-dimensional aggregates in the liquid condensed phase. The size and shape of these domains are similar to corresponding structures of classical surfactants.
Kurzfassung
Molekulare Klammern und Pinzetten können selektiv aromatische oder aliphatische Gastmoleküle aufnehmen. Diese interessanten Prozesse der molekularen Erkennung werden normalerweise in organischen oder wässrigen Lösungsmitteln untersucht. Durch die Diskrepanz zwischen polaren und hydrophoben Gruppen besitzen molekulare Klammern und Pinzetten amphiphile Eigenschaften, und sie bilden daher mono-molekulare Filme an flüssigen Phasengrenzen. In dieser Publikation haben wir die Aggregation und das Phasenverhalten der künstlichen Rezeptoren mit Hilfe von Druck-Flächen-Isothermen und der Brewsterwinkel-Mikroskopie (BAM) untersucht. Wir beobachteten runde und stäbchenförmige zweidimensionale Aggregate in flüssig-kondensierten Phasen. Die Größe und Struktur dieser Aggregate ähnelt korrespondierenden Phasen von klassischen Tensiden.
References
1. Klärner, F.-G., Benkhoff, J., Boese, R., Burkert, U., Kamieth, M. and Naatz, U.: Angewandte Chemie-International Edition in English35(10) (1996) 1130.10.1002/anie.199611301Search in Google Scholar
2. Kamieth, M. and Klärner, F.-G.: Journal für Praktische Chemie-Chemiker-Zeitung341(3) (1999) 245.10.1002/(SICI)1521-3897(199904)341:3<245::AID-PRAC245>3.0.CO;2-JSearch in Google Scholar
3. Kamieth, M., Burkert, U., Corbin, P. S., Dell, S. J., Zimmerman, S. C. and Klärner, F.-G.: European Journal of Organic Chemistry(11) (1999) 2741.10.1002/(SICI)1099-0690(199911)1999:11<2741::AID-EJOC2741>3.0.CO;2-KSearch in Google Scholar
4. Klärner, F.-G., Burkert, U., Kamieth, M., Boese, R. and Benet-Buchholz, J.: Chemistry-A European Journal5(6) (1999) 1700.10.1002/(SICI)1521-3765(19990604)5:6<1700::AID-CHEM1700>3.0.CO;2-9Search in Google Scholar
5. Klärner, F.-G., Burkert, U., Kamieth, M. and Boese, R.: Journal of Physical Organic Chemistry13(10) (2000) 604.10.1002/1099-1395(200010)13:10<604::AID-POC271>3.0.CO;2-7Search in Google Scholar
6. Klärner, F.-G., Panitzky, J., Preda, D. and Scott, L. T.: Journal of Molecular Modeling6(2) (2000) 318.10.1007/PL00010733Search in Google Scholar
7. Brown, S. P., Schaller, T., Seelbach, U. P., Koziol, F., Ochsenfeld, C., Klärner, F.-G. and Spiess, H.W.: Angewandte Chemie-International Edition40(4) (2001) 717.10.1002/1521-3773(20010216)40:4<717::AID-ANIE7170>3.0.CO;2-XSearch in Google Scholar
8. Klärner, F.-G., Panitzky, J., Blaser, D. and Boese, R.: Tetrahedron57(17) (2001) 3673.10.1016/S0040-4020(01)00230-7Search in Google Scholar
9. Jasper, C., Schrader, T., Panitzky, J. and Klärner, F-.G.: Angewandte Chemie-International Edition41(8) (2002) 1355.10.1002/1521-3773(20020415)41:8<1355::AID-ANIE1355>3.0.CO;2-6Search in Google Scholar
10. Ochsenfeld, C., Koziol, F., Brown, S. P., Schaller, T., Seelbach, U. P. and Klärner, F.-G.: Solid State Nuclear Magnetic Resonance22(2–3) (2002) 128.10.1006/snmr.2002.0085Search in Google Scholar
11. Ruloff, R., Seelbach, U. P., Merbach, A. E. and Klärner, F.-G.: Journal of Physical Organic Chemistry15(4) (2002) 189.10.1002/poc.477Search in Google Scholar
12. Review: Klärner, F.-G. and Kahlert, B.: Accounts of Chemical Research36(12) (2003) 919.Search in Google Scholar
13. Klärner, F.-G., Lobert, M., Naatz, U., Bandmann, H. and Boese, R.: Chemistry-A European Journal9(20) (2003) 5036.10.1002/chem.200304919Search in Google Scholar
14. Review: Meyer, E. A., Castellano, R. K., Diederich, F.: Angewandte Chemie International Edition in English42 (2003) 1210.10.1002/anie.200390319Search in Google Scholar
15. Hénon, S. and Meunier, J.: Reviewof Scientific Instruments95 (1991) 936.Search in Google Scholar
16. Kaerchert, T., Möbius, D. and Welt, R.: Vision Research35 (1995) 2231.Search in Google Scholar
17. Vollhardt, D.: Advances in Colloid and Interface Science64 (1996) 143.10.1016/0001-8686(95)00285-5Search in Google Scholar
18. Vollhardt, D.: Advances in Colloid and Interface Science79(1) (1999) 19.10.1016/S0001-8686(98)00073-6Search in Google Scholar
19. Hönig, D. and Möbius, D.: J. Phys. Chem.95 (1991) 4590.Search in Google Scholar
20. Adamson, A. W.: Physical Chemistry of Surfaces, 5th ed. (John Wiley & Sons, New York, Chichester, Brisbane, Toronto, Singapore1990).Search in Google Scholar
21. Hiemenz, P. C.: Principles of colloid and surface chemistry (Marcel Dekker, INC, New York, 1977).Search in Google Scholar
22. Evans, D. F. and Wennerstrom, H.: The Colloidal Domain where Physics, Chemistry, Biology and Technology Meet (VCH Publishers, INC, Weinheim, 1994).Search in Google Scholar
© 2004, Carl Hanser Publisher, Munich