Self-assembled monolayers of carceplexes on gold

Journal of the American Chemical Society

Volumn 118, Issue 14, 1996, Pages 3523-3524

  Huisman, Bart Hendrik ^a   Rudkevich, Dmitry M ^a   Van Veggel, Frank C J M ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE;

EID: 0029981404     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960031n     Document Type: Article

References (21)

1. For an overview of symmetrical carcerands, see: Cram, D. J.; Cram, J. M. In Container Molecules and their Guests in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, MA. 1994; Vol. 4. A non-symmetrical carceplex was published recently: Fraser, J. R.; Borecka, B.; Trotter, J.; Sherman J. C. J. Org. Chem. 1995, 60, 1207-1213.
2. For an overview of symmetrical carcerands, see: Cram, D. J.; Cram, J. M. In Container Molecules and their Guests in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, MA. 1994; Vol. 4. A non-symmetrical carceplex was published recently: Fraser, J. R.; Borecka, B.; Trotter, J.; Sherman J. C. J. Org. Chem. 1995, 60, 1207-1213.
3. Timmerman, P.; Verboom, W.; van Veggel, F. C. J. M.; van Duynhoven, J. P. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 2345-2348.
4. Van Wageningen, A. M. A.; van Duynhoven, J. P. M.; Verboom, W.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1995, 1941-1942.
5. For a recent review, see: (a) Dubois, L. H.; Nuzzo, R. G Annu. Rev. Phys. Chem. 1992, 43, 437-463. (b) Ulman, A. An Introduction to Ultrathin Organic Films; Academic Press: San Diego, CA, 1991.
6. For a recent review, see: (a) Dubois, L. H.; Nuzzo, R. G Annu. Rev. Phys. Chem. 1992, 43, 437-463. (b) Ulman, A. An Introduction to Ultrathin Organic Films; Academic Press: San Diego, CA, 1991.
7. For examples of monolayers with recognition sites. see: (a) Rojas, M. T.; Köninger, R.; Stoddart, J. F.; Kaifer, A. E. J. Am. Chem. Soc. 1995, 117, 336-343. (b) Adams. H.; Davis, F.; Stirling, C J. M. J. Chem. Soc., Chem. Commun. 1994, 2527-2529.
8. For examples of monolayers with recognition sites. see: (a) Rojas, M. T.; Köninger, R.; Stoddart, J. F.; Kaifer, A. E. J. Am. Chem. Soc. 1995, 117, 336-343. (b) Adams. H.; Davis, F.; Stirling, C J. M. J. Chem. Soc., Chem. Commun. 1994, 2527-2529.
9. Tnoden van Velzen, E. U : Engbersen, J. F. J.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 3597-3598.
10. Schierbaum, K.-D; Weiss, T.; Thoden van Velzen, E. U.; Engbersen, J. F. J.; Reinhoudt, D. N.; Göpel, W. Science 1994, 265, 1413-1415.
11. Porter recently reported on the S-C bond cleavage of sulfides upon adsorption to gold (Zhong, C.-J., Porter, M. D. J. Am. Chem. Soc. 1994, 116, 11616-11617). We have evidence that C-S cleavage does not occur in our case, as we will discuss in a forthcoming paper.
12. Thoden van Velzen, E. U.; Engbersen, J. F. J.; de Lange, P. J.; Many, J. W. G.; Reinhoudt, D N. J Am. Chem. Soc. 1995, 117, 6853-6862
13. Huisman, B.-H.; Thoden van Velzen, E. U , van Veggel, F. C. J. M; Engbersen, J. F. J.; Reinhoudt, D. N. Tetrahedron Lett. 1995, 36, 3273-3276.
14. Compound 2 was prepared by stepwise selective functionalization of tetrapropoxycalix[4]arene via 1,2-nitration, 3,4-iodination, and phthalimide insertion at the 3,4-positions, followed by reduction of the nitro groups and subsequent chloroacetylation (five steps). Tetrol 3 was synthesized from the corresponding resorcinarene via bromination of both the aromatic rings and the double bonds, selective debromination (recovering the double bonds), bridging of the octol, and bromo-lithium exchange, followed by quenching with trimethylborate and oxidation with hydrogen peroxide to the tetrol (four steps). Details of the synthesis will be published elsewhere.
15. The general procedure for the preparation of similar carceplexes and their properties have recently been published, see ref 2 and references cited therein.
16. +. calcd 2587.0].
17. Identical substrates and conditions were applied as decribed before in ref 9.
18. Experimental details of the analytical techniques were described in ref 9 (electrochemical analysis, contact angle measurements) and ref 10 (IR). Ellipsometry was performed on a Plasmos Ellipsometer (λ = 633 nm) assuming a refractive index of 1,50 for the monolayer. For XPS an Escalab 220 XL was used with an Al Kα monochromized source.
19. Practical Surface Analysis, 2nd ed., Briggs, D., Seah, M. P., Eds.; Wiley: Chichester, 1990: Vol 1.
20. Resistances of < 5 kΩ were determined for disordered monolayers, while the resistance of highly-ordered layers was on average 300 kΩ, and incidentally up to 800 kΩ (unpublished results).
21. Hadzi, D. In Infrared Spectroscopy and Molecular Structure, Davies, M., Ed.; Elsevier Amsterdam, 1963.