Expression of chirality by achiral coadsorbed molecules in chiral monolayers observed by STM

Angewandte Chemie - International Edition

Volumn 37, Issue 9, 1998, Pages 1223-1226

  De Feyter, Steven ^a   Grim, Petrus C M ^a   Rücker, Markus ^a   Vanoppen, Peter ^a   Meiners, Christian ^b   Sieffert, Michel ^b   Valiyaveettil, Suresh ^b   Müllen, Klaus ^b   De Schryver, Frans C ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

Chirality; Monolayers; Scanning tunneling microscopy

Indexed keywords

EID: 0032543179     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980518)37:9<1223::AID-ANIE1223>3.0.CO;2-Z     Document Type: Article

References (21)

1. L. Pasteur, C. R. Seances Acad. Sci. 1848, 26, 535-539.
2. G. Binnig, H. Rohrer, C. Gerber, E. Weibel, Phys. Rev. Lett. 1982, 49, 57-61.
3. G. Binnig, C. F. Quate, C. Gerber, Phys. Rev. Lett. 1986, 56, 930-933.
4. R. Viswanathan, J. A. Zasadzinski, D. K. Schwarz, Nature 1994, 368, 440-443.
5. D. P. E. Smith, J. Vac. Sci. Technol. B 1991, 9, 1119-1125.
6. S. J. Sowerby, W. M. Heckl, G. B. Petersen, J. Mol. Evol. 1996, 43, 419-424.
7. J. P. Rabe, S. Buchholz, Phys. Rev. Lett. 1991, 66, 2096-2099.
8. C. J. Eckhardt, N. M. Peachy, D. R. Swanson, J. M. Takacs, M. A. Khan, X. Gong, J.-H. Kim, J. Wang, R. A. Uphaus, Nature 1993, 362, 614-616.
9. a) F. Stevens, D. J. Dyer, D. M. Walba, Angew. Chem. 1996, 108, 955-957; Angew. Chem. Int. Ed. Engl. 1996, 35, 900-901;
10. a) F. Stevens, D. J. Dyer, D. M. Walba, Angew. Chem. 1996, 108, 955-957; Angew. Chem. Int. Ed. Engl. 1996, 35, 900-901;
11. b) D. M. Walba, F. Stevens, N. A. Clark, D. C. Parks. Acc. Chem. Res. 1996, 29, 591-597.
12. a) P. Nassoy, M. Goldman, O. Bouloussa, F. Rondelez, Phys. Rev. Lett. 1995, 75, 457-460.
13. b) I. Weissbuch, M. Berfeld, W. Bouman, K. Kjaer, J. Als-Nielsen, M. Lahav, L. Leisorowitz. J. Am. Chem. Soc. 1997, 119, 933-942.
14. P. Vanoppen, P. C. M. Grim, M. Rücker, S. De Feyter, G. Moessner, S. Valiyaveettil, K. Müllen, F. C. De Schryver, J. Phys. Chem. 1996, 100, 19636-19641.
15. P. C. M. Grim, S. De Feyter, A. Gesquière, P. Vanoppen, M. Rücker, S. Valiyaveettil, G. Moessner, K. Müllen, F. C. De Schryver, Angew. Chem. 1997, 109, 2713-2715; Angew. Chem. Int. Ed. Engl. 1997, 36, 2601-2603.
16. P. C. M. Grim, S. De Feyter, A. Gesquière, P. Vanoppen, M. Rücker, S. Valiyaveettil, G. Moessner, K. Müllen, F. C. De Schryver, Angew. Chem. 1997, 109, 2713-2715; Angew. Chem. Int. Ed. Engl. 1997, 36, 2601-2603.
17. Positive is defined as going clockwise from the normal towards the orientation of the organized structure. The normal can be related to the graphite axis (θ) or the lamellar axis (φ; Figure 2).
18. Our conclusions are based upon approximately 50 STM images for each enantiomer. None of the STM images obtained are in contradiction with the results outlined in the text.
19. This compound forms two types of monolayer structures. Some domains are completely disorded and contain ringlike structures, individual small lamellae, etc. Other domains are composed of lamellae, but the lamellar width (20 ± 1 Å) and the intralamellar distance between two head groups (8.4 ± 0.2 Å) are much smaller than the values obtained for ISA molecules. The angle between the alkoxy chains and the lamellar axis measures approximately 43 ± 2°. No codeposition of solvent molecules was observed. These large deviations are most likely due to the presence of an ether functionality in the alkyl chain and the absence of a stereogenic center. In ISA these stereogenic centers force, probably because of sterical hindrance, the side chains to adapt an extended conformation that is almost perpendicular to the lamellar axis.
20. K. Freudenberg, W. Lwowski, Justus Liebigs Ann. Chem. 1955, 594, 76-88.
21. M. Hjalmarsson, H.-E. Högberg, Acta Chem. Scand. Ser. B 1985, 39, 793-796.