AND/OR bimolecular recognition

Journal of the American Chemical Society

Volumn 126, Issue 22, 2004, Pages 6846-6847

  Yoshizawa, Michito ^a   Tamura, Masazumi ^a   Fujita, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE; ALKANE; AZULENE; CORONENE; PYRENE; TRIPHENYLENE; UNCLASSIFIED DRUG;

ALLOSTERISM; ARTICLE; BIMOLECULAR RECOGNITION; BINDING AFFINITY; CHEMICAL INTERACTION; CHEMICAL REACTION; COMPLEX FORMATION; CONFORMATION; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 3042734784     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048860t     Document Type: Article

References (22)

1. (a) Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Nature 1998, 394, 764.
2. (b) Shivanyuk, A.; Scarso, A.; Rebek, J., Jr. Chem. Commun. 2003, 1230.
3. Kim, H.-J.; Heo, J.; Jeon, W. S.; Lee, E.; Kim J.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 1526.
4. Fenyvesi, E.; Szente, L.; Russell, N. R.; McNamara, M. Comprehensive Supramolecular Chemistry; Szejtli, J., Osa, T., Eds.; Pergamon: Oxford, UK, 1996; Vol. 3, Chapter 10.
5. (a) Mackay, L. G.; Wylie, R. S.; Sanders, J. K. M. J. Am. Chem. Soc. 1994, 116, 3141.
6. (b) Walter, C. J.; Sanders, J. K. M. Angew., Chem. Int. Ed. Engl. 1995, 34, 217.
7. (a) Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50.
8. (b) Kang, J.; Hilmersson, G.; Santamaría, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650.
9. Yoshizawa, M.; Takeyama, T.; Okano, T.; Fujita, M. J. Am. Chem. Soc. 2003, 125, 3243.
10. Ebbing, M. H. K.; Villa, M.-J.; Valpuesta, J.-M.; Prados, P.; de Mendoza, J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4962.
11. Atwood, J. L.; Szumna, A. Chem. Commun. 2003, 940.
12. Molecular AND logic gates: (a) de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. N. Nature 1993, 364, 42.
13. (b) Iwata, S.; Tanaka, K. Chem. Commun. 1995, 1491.
14. (c) Inouye, M.; Akamatsu, K.; Nakazumi, H. J. Am. Chem. Soc. 1997, 119, 9160.
15. (d) Cooper, C. R.; James, T. D. Chem. Commun. 1997, 1419.
16. Molecular OR logic gates: (a) de Silva, A. P.; Gunaratne, H. Q. N.; Maguire, G. E. M.Chem. Commun. 1994, 1213.
17. (b) Ghosh, P.; Bharadwaj, P. K.; Mandal, S.; Ghosh, S. J. Am. Chem. Soc. 1996, 118, 1553.
18. Our recent reports: (a) Kusukawa, T.; Yoshizawa, M.; Fujita, M. Angew. Chem., Int. Ed. 2001, 40, 1879.
19. (b) Yoshizawa, M.; Takeyama, T.; Kusukawa, T.; Fujita, M. Angew. Chem., Int. Ed. 2002, 41, 1347.
20. (c) Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 2002, 124, 13576.
21. We suggest that a planar aromatic guest gains stabilization by stacking on the ligand while a flexible aliphatic guest enhances it by filling the void. Such cooperation of the two different guests can account for the AND bimolecular recognition.
22. Guests 3-5 are too large to self-associate in the cavity. Thus, only AND recognition takes place. In contrast, relatively small 8 or 9 can self-associate in the cavity and experience OR recognition, where donor-acceptor stacking between 8 and 9 may be important.