Dimensional matching of polycyclic aromatics with rectangular metallacycles: Insertion modes determined by [C-Hπ] interactions

Chemistry - A European Journal

Volumn 19, Issue 45, 2013, Pages 15329-15335

  Alvariño, Cristina ^a   Pía, Elena ^a   García, Marcos D ^a   Blanco, Víctor ^a,b   Fernández, Alberto ^a   Peinador, Carlos ^a   Quintela, José M ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

host guest systems; molecular recognition; pi interactions; self assembly; supramolecular chemistry

Indexed keywords

BENZO [A] PYRENE; CAVITY LENGTH; HOST-GUEST SYSTEM; INCLUSION COMPLEX; PI INTERACTIONS; POLYCYCLIC AROMATICS; SIZE AND SHAPE; SPECIFIC BINDING;

BINDING ENERGY; MOLECULAR RECOGNITION; NAPHTHALENE; PLATINUM; PYRENE; SELF ASSEMBLY; SOLUTIONS; SUPRAMOLECULAR CHEMISTRY;

SUBSTRATES;

EID: 84886642207     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201302165     Document Type: Article

References (50)

1. C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017.
2. Inclusion Phenomena and Molecular Recognition (Ed.:, J. L. Atwood,), Plenum, New York, 1990
3. Host-Guest Complex Chemistry: Synthesis Structure, Applications (Eds.:, F. Vögtle, E. Weber,), Springer-Verlag, Berlin, 1985.
4. Molecular Catenanes, Rotaxanes and Knots, A Journey Through the World of Molecular Topology (Eds.:, J.-P. Sauvage, C. Dietrich-Buchecker,), Wiley-VCH, Weinheim, 1999
5. L. Fang, M. A. Olson, D. Benitez, E. Tkatchouk, W. A. Goddard, J. F. Stoddart, Chem. Soc. Rev. 2010, 39, 17
6. R. Chakrabarty, P. S. Mukherjee, P. J. Stang, Chem. Rev. 2011, 111, 6810
7. M. Fujita, M. Tominaga, A. Hori, B. Therrien, Acc. Chem. Res. 2005, 38, 369.
8. D. Ma, G. Hettiarachchi, D. Nguyen, B. Zhang, J. B. Wittenberg, P. Y. Zavalij, V. Briken, L. Isaacs, Nat. Chem. 2012, 4, 503
9. K. H. Frömming, in Comprehensive Supramolecular Chemistry, Vol. 10 (Eds.:, J. L. Atwood, J.-M. Lehn, J. E. D. Davies, D. D. MacNicol, F. Vögtle,), Elsevier, Amsterdam, 1996, p 445.
10. M. Teresa Albelda, J. C. Frías, E. García-España, H.-J. Schneider, Chem. Soc. Rev. 2012, 41, 3859.
11. D. Ramaiah, P. P. Neelakandan, A. K. Nair, R. R. Avirah, Chem. Soc. Rev. 2010, 39, 4158
12. M. D. Ward, P. R. Raithby, Chem. Soc. Rev. 2013, 42, 1619.
13. L. Marchetti, M. Levine, ACS Catal. 2011, 1, 1090
14. M. Yoshizawa, J. K. Klosterman, M. Fujita, Angew. Chem. 2009, 121, 3470
15. Angew. Chem. Int. Ed. 2009, 48, 3418
16. M. D. Pluth, R. G. Bergman, K. N. Raymond, Acc. Chem. Res. 2009, 42, 1650
17. R. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997.
18. K. N. Houk, A. G. Leach, S. P. Kim, X. Zhang, Angew. Chem. 2003, 115, 5020
19. Angew. Chem. Int. Ed. 2003, 42, 4872.
20. M. V. Rekharsky, Y. Inoue, Chem. Rev. 1998, 98, 1875
21. G. Chen, M. Jiang, Chem. Soc. Rev. 2011, 40, 2254.
22. C. D. Gutsche, Calixarenes: An Introduction, 2 nd ed, Royal Society of Chemistry, Cambridge, 2008
23. R. Gramage-Doria, D. Armspach, D. Matt, Coord. Chem. Rev. 2013, 257, 776.
24. F. Diederich, Angew. Chem. 1988, 100, 372
25. Angew. Chem. Int. Ed. Engl. 1988, 27, 362
26. E. Masson, X. X. Ling, R. Joseph, L. Kyeremeh-Mensah, X. Y. Lu, RSC Adv. 2012, 2, 1213
27. M. Xue, Y. Yang, X. D. Chi, Z. B. Zhang, F. H. Huang, Acc. Chem. Res. 2012, 45, 1294
28. C. Naumann, E. Roman, C. Peinador, T. Ren, B. O. Patrick, A. E. Kaifer, J. C. Sherman, Chem. Eur. J. 2001, 7, 1637.
29. Y.-F. Han, H. Li, G.-X. Jin, Chem. Commun. 2010, 46, 6879
30. Y.-F. Han, W.-G. Jia, Y.-J. Lin, G.-X. Jin, Angew. Chem. 2009, 121, 6352
31. Angew. Chem. Int. Ed. 2009, 48, 6234
32. T. Wu, L.-H. Weng, G.-X. Jin, Chem. Commun. 2012, 48, 4435
33. T. Wu, Y.-J. Lin, G.-X. Jin, RSC Adv. 2013, 3, 11476.
34. C. Peinador, E. Pía, V. Blanco, M. D. García, J. M. Quintela, Org. Lett. 2010, 12, 1380
35. V. Blanco, M. D. García, A. Terenzi, E. Pía, A. Fernández-Mato, C. Peinador, J. M. Quintela, Chem. Eur. J. 2010, 16, 12373.
36. J. C. Barnes, M. Juríček, N. L. Strutt, M. Frasconi, S. Sampath, M. A. Giesener, P. L. McGrier, C. J. Bruns, C. L. Stern, A. A. Sarjeant, J. F. Stoddart, J. Am. Chem. Soc. 2013, 135, 183.
37. M. Nishio, M. Hirota, Y. Umezawa, The CH/π Interaction: Evidence, Nature, and Consequences, Wiley-VCH, Weinheim, 1998.
38. C. Peinador, V. Blanco, M. D. García, J. M. Quintela, in Molecular Self-Assembly: Advances and Applications, (Ed.:, A. D. Q. Li,), Pan Stanford Publishing, Singapore 2012, p. 351.
39. M. Chas, C. Platas-Iglesias, C. Peinador, J. M. Quintela, Tetrahedron Lett. 2006, 47, 3119.
40. V. Blanco, A. Gutierrez, C. Platas-Iglesias, C. Peinador, J. M. Quintela, J. Org. Chem. 2009, 74, 6577
41. V. Blanco, M. D. Garcia, C. Peinador, J. M. Quintela, Chem. Sci. 2011, 2, 2407
42. V. Blanco, D. Abella, E. Pia, C. Platas-Iglesias, C. Peinador, J. M. Quintela, Inorg. Chem. 2009, 48, 4098
43. V. Blanco, M. Chas, D. Abella, E. Pia, C. Platas-Iglesias, C. Peinador, J. M. Quintela, Org. Lett. 2008, 10, 409.
44. D. Abella, V. Blanco, E. Pia, M. Chas, C. Platas-Iglesias, C. Peinador, J. M. Quintela, Chem. Commun. 2008, 2879.
45. 2]
46. L. V. Popov, N. N. Zheligovskaya, A. M. Grevtsev, E. A. Kharina, V. I. Spitsyn, Seriya Khimicheskaya 1977, 7, 1677
47. M. Fujita, J. Yazaki, K. Ogura, Chem. Lett. 1991, 1031.
48. G. M. Sheldrick, SHELX-97, An Integrated System for Solving and Refining Crystal Structures from Diffraction Data, University of Göttingen, Göttingen, 1997
49. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112.
50. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837.