Molecules with new topologies derived from hydrogen-bonded dimers of tetraurea calix[4]arenes

Chemistry - A European Journal

Volumn 14, Issue 28, 2008, Pages 8514-8520

  Bogdan, Anca ^a   Bolte, Michael ^b   Böhmer, Volker ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b GOETHE UNIVERSITY   (Germany)

Author keywords

Calixarenes; Dimers; Knots; Macrocycles; Topology

Indexed keywords

AROMATIC COMPOUNDS; HYDROGEN; OLIGOMERS;

CALIXARENES; DIMERS; KNOTS; MACROCYCLES; TOPOLOGY;

UREA;

CALIX(4)ARENE; CALIXARENE; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; ELECTROSPRAY MASS SPECTROMETRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CALIXARENES; DIMERIZATION; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PHENOLS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 53849121654     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801268     Document Type: Article

References (34)

1. Molecular Catenanes, Rotaxanes, and Knots (Eds.: J.-P. Sauvage, C. Dietrich-Buchecker), Wiley-VCH, Weinheim, 1999; for a recent appealing example,
2. see: K. S. Chichak, S. J. Cantrill, A. R. Pease, S. H. Chiu, G. W. V. Cave, J. L. Atwood, J. F. Stoddart, Science 2004, 304, 1308-1312.
3. For an actual review on "Templated Synthesis of Interlocked Molecules", see: F. Aricó, J. D. Badjic, S. J. Cantrill, A. H. Flood, K. C.-F. Leung, Y. Liu, J. F. Stoddart, Top. Curr. Chem. 2005, 249, 203-259.
4. For early publications, see: K. D. Shimizu, J. Rebek, Jr., Proc. Natl. Acad. Sci. USA 1995, 92, 12403-12407;
5. B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425-1427;
6. Angew. Chem. Int. Ed. Engl. 1996, 35, 1326-1329;
7. O. Mogck, V. Böhmer, W. Vogt, Tetrahedron 1996, 52, 8489-8496.
8. For reviews, see: J. Rebek, Jr., Chem. Commun. 2000, 637-643;
9. V. Böhmer, M. O. Vysotsky. Aust. J. Chem. 2001, 54, 671-677.
10. A. Bogdan, Y. Rudzevich, M. O. Vysotsky, V. Böhmer, Chem. Commun. 2006, 2941-2952.
11. M. O. Vysotsky, A. Bogdan, L. Wang, V. Böhmer, Chem. Commun. 2004, 1268-1269.
12. For the heterodimerization of aryl and losylureas, see: R. K. Castellano, B. H. Kim, J. Rebek, Jr., J. Am. Chem. Soc. 1997, 119, 12671-12672;
13. R. K. Castellano, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 3657-3663;
14. Y. Rudzevich, M. O. Vysotsky, V. Böhmer, M. S. Brody, J. Rebek, Jr., F. Broda, I. Thondorf, Org. Biomol. Chem. 2004, 2, 3080-3084.
15. O. Molokanova, M. O. Vysotsky, Y. Cao, I. Thondorf, V. Böhmer, Angew. Chem. 2006, 118, 8220-8224;
16. Angew. Chem. Int. Ed. 2006, 45, 8051-8055.
17. M. O. Vysotsky, A. Bogdan, T. Ikai, Y. Okamoto, V. Böhmer, Chem. Eur. J. 2004, 10, 3324-3330.
18. L. Wang, M. O. Vysotsky, A. Bogdan, M. Boite, V. Böhmer, Science 2004, 504, 1312-1314.
19. This was shown for homodimers of tetraalkenyl tetraureas, which gave in addition to bis[2]calenanes (2 a connections) doubly bridged monocatenanes (α and β connection) and tetrabridged dimers (2 β connections); see M. O. Vysotsky, M. Bolte, I. Thondorf, V. Böhmer, Chem. Eur. J. 2003, 9, 3375-3382.
20. D. Braekers, C. Peters, A. Bogdan, Y. Rudzevich, V. Böhmer, J. F. Desreux, I Org. Chem. 2008, 73, 701-706;
21. Y. Rudzevich, Y. Cao, V. Rudzevich, V. Böhmer, Chem. Eur. J. 2008, 14, 3346-3354.
22. M. Saadioui, A. Shivanyult, V. Böhmer, W. Vogt, J. Org. Chem. 1999, 64, 3774-3777.
23. A. Bogdan, M. O. Vysotsky, T. Ikai, Y. Okamoto, V. Böhmer, Chem. Eur. J. 2004, 10, 3324-3330.
24. A. Pop, M. O. Vysotsky, M. Saadioui, V. Böhmer, Chem. Commun. 2003, 1124-1125.
25. The two few-butyl groups in the 3,5-position are identical due to fast rotation around the aryl-N bond.
26. Despite their size, tetraethylammonium cations are preferentially included as guest: for an X-ray structure, see: I. Thondorf, F. Broda, K. Rissanen, M. Vysotsky, V. Böhmer, J. Chem. Soc. Perkin Trans. 2 2002, 1796-1800:
27. this inclusion has been used for the mass spectroscopic analysis of dimeric capsules, see: C. A. Schalley, R. K. Castellano, M. S. Brody, D. M. Rudkevich, G. Siuzdak, J. Rebek, Jr., J. Am. Chem. Soc. 1999, 121, 4568-4579.
28. O. Mogck, E. F. Paulus, V. Böhmer, I. Thondorf, W. Vogt, Chem. Commun. 1996, 2533-2534.
29. For further crystal structures of tetraurea dimers. see ref. [11] and O. Molokanova, A. Bogdan, M. O. Vysotsky, M. Bolte, T. Ikai, Y. Okamoto, V. Böhmer, Chem. Eur. J. 2007, 13, 6157-6170:
30. M. Bolte, I. Thondorf, V. Böhmer, V. Rudzevich, Y. Rudzevich, CrystEngComm 2008, 10, 270-272.
31. These values are the average for two crystallographically independent molecules present also in the former structure.
32. R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-38.
33. G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473.
34. G. M. Sheldrick, SHELXL-97, A Program for the Refinement of Crystal Structures, University of Göttingen. Göttingen (Germany), 1997.