Langmuir-blodgett mono- and multilayers of rodlike oligo(cyclohexylidene) derivatives bearing an oxime headgroup

Langmuir

Volumn 12, Issue 20, 1996, Pages 4760-4767

  Hoogesteger, Frans J ^a   Kroon, Johannes M ^b   Jenneskens, Leonardus W ^a   Sudhölter, Ernst J R ^b   De Bruin, Theodorus J M ^a   Zwikker, Jan W ^a   Ten Grotenhuis, Erik ^a   Marée, Chrysostomus H M ^a   Veldman, Nora ^c   Spek, Anthony L ^c  

^a UTRECHT UNIVERSITY   (Netherlands)

^b WAGENINGEN UNIVERSITY   (Netherlands)

^c UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000493168     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la9510590     Document Type: Article

References (41)

1. (a) Roberts, G. G. In Langmuir-Blodgett Films; Roberts, G. G., Ed.; Plenum Press: New York, 1990; Chapter 7.
2. (b) Ulman, A. An Introduction to Ultrathin Organic Films; Academic Press: London, 1991; Chapter 5.
3. (a) Tachibana, H.; Matsumoto, M. Adv. Mater. 1993, 5, 796.
4. (b) Swalen, J. D.; Allara, D. L.; Andrade, J. D.; Chandross, E. A.; Garoff, S.; Israelachvili, J.; McCarthy, T. J.; Murray, R.; Pease, R. F.; Rabolt, J. F.; Wynne, K. J.; Yu, H. Langmuir 1987, 3, 932.
5. Hoogesteger,F. J.; Havenith, R. W. A.; Zwikker, J. W.; Jenneskens, L. W.; Kooijman, H.; Veldman, N.; Spek, A. L. J. Org. Chem. 1995, 60, 4375.
6. Veldman, N.; Spek, A. L.; Hoogesteger, F. J.; Zwikker, J. W.; Jenneskens, L. W. Acta Crystallogr. 1994, C50, 742.
7. (a) Hoogesteger, F. J.; Jenneskens, L. W.; Kooijman, H.; Veldman, N.; Spek, A. L. Tetrahedron 1996, 52, 1773.
8. (b) ten Grotenhuis, E.; van der Eerden, J. P.; Hoogesteger, F. J.; Jenneskens, L. W. Chem. Phys. Lett. 1996, 250, 549.
9. (c) ten Grotenhuis, E.; van der Eerden, J. P.; Hoogesteger, F. J.; Jenneskens, L. W. Adv. Mater., in press.
10. Adam, N. K. Trans. Faraday Soc. 1928, 24, 149.
11. Chaiko, D. J.; Osseo-Asare, K. Sep. Sci. Technol. 1988, 23, 1423.
12. Yang, H. C.; Magnera, T. F.; Lee, C.; Bard, A. J.; Michl, J. Langmuir 1992, 8, 2740.
13. (a) Daniel, M. F.; Lettington, O. C.; Small, S. M. Thin Solid Films 1983, 99, 61.
14. (b) Daniel, M. F.; Lettington, O. C.; Small, S. M. Mol. Cryst. Liq. Cryst. 1983, 96, 373.
15. Hoogesteger, F. J.; Grove, D. M.; de Bruin, T. J. M.; Jansen, B. A. J.; Jenneskens, L. W. J. Chem. Soc., Perkin Trans. 2, in press.
16. Atomic coordinates (including calculated H atom coordinates), thermal parameters, bond lengths, and bond angles for the crystal structure determination of compounds 4 and 5(1) have been deposited at the Cambridge Crystallographic Data Centre. They can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 IEZ, U.K.
17. Sheldrick, G. M. SHELXS86, Program for crystal structure determination; University of Göttingen: Göttingen, Germany, 1986.
18. Sheldrick, G. M. SHELXL-93, Program for crystal structure refinement; University of Göttingen: Göttingen, Germany, 1993.
19. Cohen Stuart, M. A.; Wegh, R.; Kroon, J. M.; Sudhölter, E. J. R. To be published.
20. Arnold Bik, W. M.; Habraken, F. H. P. M. Rep. Prog. Phys. 1993, 56, 859.
21. Arnold Bik, W. M.; de Laat, C. T. A. M.; Habraken, F. H. P. M. Nucl. Instrum. Methods Phys. Res., Sect. B 1992, 64, 832.
22. Mareé, C. H. M.; Kleinpenning, A.; Vredenberg, A. M.; Habraken, F. H. P. M. Nucl. Instrum. Methods Phys. Res., Sect. B, in press.
23. Marée, C. H. M.; Savenije, J.; Schaafsma, T. J.; Habraken, F. H. P. M. Appl. Surf. Sci., in press.
24. Becker, D. P.; Flynn, D. L. Synthesis 1992, 1080.
25. (a) Eliel, E. L. Stereochemistry of Carbon Compounds; McGraw-Hill: New York, 1962.
26. (b) Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 4973.
27. Kurtz, A. P.; D'Silva, T. D. J. J. Pharm. Sci. 1987, 76, 599.
28. Gaines, G. L., Jr. Insoluble Monolayers at Liquid-Gas Interfaces; John Wiley and Sons: New York, 1966.
29. Spek, A. L. PLUTON; Utrecht University: Utrecht, The Netherlands, 1993.
30. Smith, R. D.; Berg, J. C. J. Colloid Interface Sci. 1980, 74, 273.
31. Baker, S.; Petty, M. C.; Roberts, G. G.; Twigg, M. V. Thin Solid Films 1983, 99, 53.
32. (a) Honig, D.; Overbeck, G. A.; Möbius, D. Adv. Mater. 1992, 4, 419.
33. (b) Honig, D.; Möbius, D. Thin Solid Films 1992, 210/211, 64.
34. (c) Hénon, S.; Meunier, J. Rev. Sci. Instrum. 1991, 62, 936. BAM gives insight in monolayer morphology without the necessity of introducing probe molecules into the film.
35. (a) Lu, Z.; Nakahara, H. Chem. Lett. 1994, 2005.
36. (b) Wolthaus, L.; Schaper, A.; Möbius, D. J. Phys. Chem. 1994, 98, 10809.
37. Kroon, J. M.; Sudhölter, E. J. R.; Schenning, A. P. H. J.; Nolte, B. J. M. Langmuir 1995, 11, 214.
38. 1 Transfer of a mixed Langmuir film (molar ratio 1(2)/stearic acid 1:2.5) onto silicon (100) wafer (cleaned with 2-propanol) gave standard Y-type deposition during the buildup of a 20 layer assembly at π = 15 mN/m.
39. Popovitz-Biro, R.; Hill, K.; Shavit, E.; Hung, D. J.; Lahav, M.; Leiserowitz, L.; Sagiv, J.; Hsiung, H.; Meredith, G. R.; Vanherzeele, H. J. Am. Chem. Soc. 1990, 112, 2498.
40. Frommer, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1298.
41. MMX force field as implemented in PCMODEL 4.0, Serena Software, Bloomington, IN, 1990. An inspection of space-filling molecular models reveals that the best two-dimensional packing of 5(2), in which the tert-butyl groups are at Van Jer Waals distances, gives a tilt angle of ca. 27°, which is in good agreement with the value obtained from the AFM image.