Controlling the extent of spin exchange coupling in 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO) biradicals via molecular recognition with cucurbit[ n ]uril hosts

Langmuir

Volumn 27, Issue 9, 2011, Pages 5624-5632

  Yi, Song ^a   Captain, Burjor ^a   Ottaviani, M Francesca ^b   Kaifer, Angel E ^a  

^a Department of Biology   (United States)

^b UNIVERSITY OF URBINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING INTERACTION; BIRADICALS; COBALTOCENIUM; CUCURBIT[7]URIL; CUCURBIT[N]URIL; ELECTRON PARAMAGNETIC RESONANCE SPECTROSCOPY; ELECTRONIC ABSORPTION; EQUILIBRIUM ASSOCIATION CONSTANT; HOST MOLECULES; INCLUSION COMPLEX; NITROXIDES; SINGLE CRYSTAL X-RAY DIFFRACTION; SPIN-EXCHANGE COUPLING; TERNARY COMPLEX;

ABSORPTION SPECTROSCOPY; BINDING ENERGY; COMPLEXATION; CRYSTAL STRUCTURE; EXCHANGE COUPLING; MASS SPECTROMETRY; MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; ORGANOMETALLICS; PARAMAGNETIC MATERIALS; PARAMAGNETIC RESONANCE; PARAMAGNETISM; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

ELECTRON SPIN RESONANCE SPECTROSCOPY;

EID: 79955152288     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la2005198     Document Type: Article

References (35)

1. Mezzina, E.; Cruciani, F.; Pedulli, G. F.; Lucarini, M. Chem.-Eur. J. 2007, 13, 7223-7233
2. Mileo, E.; Mezzina, E.; Grepioni, F.; Pedulli, G. F.; Lucarini, M. Chem.-Eur. J. 2009, 15, 7859-7862
3. Bardelang, D.; Banaszak, K.; Karoui, H.; Rockenbauer, A.; Waite, M.; Udachin, K.; Ripmeester, J. A.; Ratcliffe, C. I.; Ouari, O.; Tordo, P. J. Am. Chem. Soc. 2009, 131, 5402-5404
4. Kirilyuk, I.; Polovyanenko, D.; Semenov, S.; Grigor'ev, I.; Gerasko, O.; Fedin, V.; Bagryanskaya, E. J. Phys. Chem. B 2010, 114, 1719-1728
5. Franchi, P.; Lucarini, M.; Pedulli, G. F. Curr. Org. Chem. 2004, 8, 1831-1849
6. Maliakal, A. J.; Turro, N. J.; Bosman, A. W.; Cornel, J.; Meijer, E. W. J. Phys. Chem. A 2003, 107, 8467-8475
7. Lucarini, M.; Luppi, B.; Pedulli, G. F.; Roberts, B. P. Chem.-Eur. J. 1999, 5, 2048-2054
8. Sobransingh, D.; Kaifer, A. E. Langmuir 2006, 22, 10540-10544
9. Cui, L.; Gadde, S.; Li, W.; Kaifer, A. E. Langmuir 2009, 25, 13763-13769
10. Weil, J. A.; Bolton, J. R.; Wertz, J. E. In Electron Paramagnetic Resonance; Wiley- Interscience: Hoboken, NJ, 2007.
11. A ferrocene-based precedent for biradical 2 has been described: Nickel, B.; Rassat, A. Tet. Lett. 1978, 7, 633-636
12. Nickel, B.; Rassat, A. Tet. Lett. 1980, 21, 2409-2412
13. Mezzina, E.; Fanì, M.; Ferroni, F.; Franchi, P.; Menna, M.; Lucarini, M. J. Org. Chem. 2006, 71, 3773-3777
14. Ionita, G.; Meltzer, V.; Pincu, E.; Chechik, V. Org. Biomol. Chem. 2007, 5, 1910-1914
15. Gagnaire, G.; Michon, J.; Pierre, J. L. New J. Chem. 1992, 16, 915-918
16. Harten, B.; Darcy, R.; Lyons, R. New J. Chem. 1986, 10, 569-571
17. Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844-4870
18. Mileo, E.; Yi, S.; Bhattacharya, P.; Kaifer, A. E. Angew. Chem., Int. Ed. 2009, 48, 5337-5339
19. Yi, S.; Mileo, E.; Kaifer, A. E. Org. Lett. 2009, 11, 5690-5693
20. 2) was 0.0481 for 3620 reflections I > 2σ(I).
21. 2) was 0.0387 for 4024 reflections I > 2σ(I).
22. Ong, W.; Kaifer, A. E. Organometallics 2003, 22, 4181-4183
23. Liu, S.; Ruspic, C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 15959-15967
24. 2) was 0.0582 for 9919 reflections I > 2σ(I).
25. Jayaraj, N.; Porel, M.; Ottaviani, M. F.; Maddipatla, M. V. S. N.; Modelli, A.; Da Silva, J. P.; Bhogala, B. R.; Captain, B.; Jockusch, S.; Turro, N. J.; Ramamurthy, V. Langmuir 2009, 25, 13820-13832
26. Porel, M.; Ottaviani, M. F.; Jockusch, S.; Jayaraj, N.; Turro, N. J.; Ramamurthy, V. Chem. Commun. 2010, 46, 7736-7738
27. Sheats, J. E.; Rausch, M. D. J. J. Org. Chem. 1970, 35, 3245
28. Harmon, K. M.; Nowos, L. S. J. Mol. Struct. 1991, 249, 141-147
29. Harmon, K. M.; Southworth, B. A.; Wilson, K. E.; Keefer, P. K. J. Org. Chem. 1993, 58, 7294-7295
30. Day, A.; Arnold, A. P.; Blanch, R. J.; Snushall, B. J. Org. Chem. 2001, 66, 8094-8100
31. Frisch, M. J. Gaussian 03, Revision D.1; Gaussian, Inc.: Wallingford, CT, 2004.
32. Budil, D. E.; Lee, S.; Saxena, S.; Freed, J. H. J. Magn. Res. A 1996, 120, 155-189
33. Apex2, version 2.2-0, and SAINT+, version 7.46A; Bruker Analytical X-ray System, Inc.: Madison, WI, 2007.
34. Sheldrick, G. M. SHELXTL, version 6.1; Bruker Analytical X-ray Systems, Inc.: Madison, WI, 2000.
35. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2008.