Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter May 1, 2013

Characterization of Langmuir-Monolayers of Molecular Tweezers and Clips by Means of Brewster-Angle-Microscopy

Charakterisierung der Langmuir-Monoschichten von molekularen Pinzetten und Klammern mit Hilfe der Brewsterwinkel-Mikroskopie
  • H. Rehage , B. Achenbach , F.-G. Klärner , M. Kamieth and J. Panitzky

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.


Correspondence to Prof. Dr. Heinz Rehage Universität Duisburg-Essen Institut für Physikalische Chemie Universitätsstr. 2–5, 45141 Essen Germany E-mail:

Prof. Heinz Rehage (born in 1952) studied chemistry at the universities of Clausthal-Zellerfeld, Göttingen and Bayreuth. After completing his studies, he spend one year at the Collège de France in Paris. Since 1991, he has been C3-professor of the “Hans-Goldschmidt Foundation” at the University of Essen. In 2003, he was appointed to a full position as C4-professor in the department of Physical Chemistry at the University of Dortmund, and since 2004 he is treasurer of the German Colloid Society.

Barbara Achenbach (born in 1966) studied chemistry at the University of Essen from 1987 – 1995 and graduated there in July 1995. During her doctoral thesis she investigated ultra-thin films by means of Brewster-Angle microscopy. She obtained her Ph. D. in 2002 und after that time she joined the “Metallgesellschaft AG” in Frankfurt (Germany), where she works now as research scientist in the department of Technology Development.

Prof. Frank-Gerrit Klärner (born 1941) studied chemistry at the University of Köln (Cologne) and received his Ph. D. in 1968 from the University of Köln. In 1974 he finished his “Habilitation” at the Ruhr-University of Bochum, was associate professor in Bochum from 1980–1992, and visiting professor at University of Wisconsin, Madison, USA in 1983. Since 1992 he is full professor at the University of Essen and chairs the DFG center of supramolecular research at the Universities of Essen and Bochum (“Sonderforschungsbereich, SFB 452”) since 1998.

Markus Kamieth (born 1970) studied chemistry at the University of Essen from 1990–1995 and graduated there in October 1995. During his Ph.D. thesis he investigated the synthesis and supramolecular properties of molecular tweezers as synthetic receptors in host guest chemistry. He obtained his Ph. D. in 1998 and joined the BASF as a research scientist.

Jens Panitzky (born 1972) studied chemistry at the University of Essen from 1993 – 1998 and graduated there in October 1998. During his Ph. D. thesis he investigated the synthesis and supramolecular properties of molecular clips. He obtained his Ph. D. in 2001 and joined first the “Fraunhofer Institut” as postdoctorate research fellow for one year and works now as a research scientist in the Ticona company.


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

Received: 2004-4-5
Published Online: 2013-05-01
Published in Print: 2004-06-01

© 2004, Carl Hanser Publisher, Munich

Downloaded on 29.3.2024 from https://www.degruyter.com/document/doi/10.3139/113.100215/html
Scroll to top button