Halide anion-templated assembly of di- and triiodoperfluorobenzenes into 2D and 3D supramolecular networks

Journal of Fluorine Chemistry

Volumn 131, Issue 11, 2010, Pages 1165-1172

  Cavallo, Gabriella ^a   Biella, Serena ^a   Lü, Jian ^a   Metrangolo, Pierangelo ^a   Pilati, Tullio ^b   Resnati, Giuseppe ^a,b   Terraneo, Giancarlo ^a  

^a POLITECNICO DI MILANO   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

Crystal engineering; Fluorobenzene; Halide anions; Halogen bonding; Self assembly; Supramolecular chemistry

Indexed keywords

EID: 77955793602     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2010.05.004     Document Type: Article

References (76)

1. P. Metrangolo, and G. Resnati Science 321 2008 918 919
2. A. Farina, S.V. Meille, M.T. Messina, P. Metrangolo, and G. Resnati Angew. Chem., Int. Ed. 38 1999 2433 2436
3. E. Corradi, S.V. Meille, M.T. Messina, P. Metrangolo, and G. Resnati Tetrahedron Lett. 40 1999 7519 7523
4. E. Corradi, S.V. Meille, M.T. Messina, P. Metrangolo, and G. Resnati Angew. Chem., Int. Ed. 39 2000 1782 1786
5. A. Lunghi, P. Cardillo, M.T. Messina, P. Metrangolo, and G. Resnati J. Fluor. Chem. 91 1998 191 194
6. M.T. Messina, P. Metrangolo, W. Panzeri, E. Ragg, and G. Resnati Tetrahedron Lett. 39 1998 9069 9072
7. P. Metrangolo, H. Neukirch, T. Pilati, and G. Resnati Acc. Chem. Res. 38 2005 386 395
8. A. Karpfen P. Metrangolo, G. Resnati, Halogen Bonding Fundamentals and Applications 2008 Springer Berlin 1 16
9. F.F. Awwadi, R.D. Willet, K.A. Peterson, and B. Twamley Chem. Eur. J. 12 2006 8952 8960
10. P. Politzer, P. Lane, M.C. Concha, Y. Ma, and J.S. Murray J. Mol. Model. 13 2007 305 311
11. P. Auffinger, F.A. Hays, E. Westhof, and P.S. Ho Proc. Natl. Acad. Sci. U.S.A. 101 2004 16789 16794
12. J.S. Murray, M.C. Concha, P. Lane, P. Hobza, and P. Politzer J. Mol. Model. 14 2008 699 704
13. P. Politzer, J.S. Murray, and M.C. Concha J. Mol. Model. 14 2008 659 665
14. T. Brinck, J.S. Murray, and P. Politzer Int. J. Quant. Chem.: Quant. Biol. Symp. 19 1992 57 64
15. F. Guthrie J. Chem. Soc. 16 1863 239 244
16. D.S. Reddy, D.C. Craig, A.D. Rae, and G.R. Desiraju J. Chem. Soc., Chem. Commun. 23 1993 1737 1739
17. R.D. Bailey, G.W. Drake, M. Grabarczyk, T.W. Hanks, L.L. Hook, and W.T. Pennington J. Chem. Soc., Perkin Trans. 2 1997 2773 2779
18. E.L. Rimmer, R.D. Bailey, T.W. Hanks, and W.T. Pennington Chem. Eur. J. 6 2000 4071 4081
19. P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, and G. Terraneo Angew. Chem., Int. Ed. 47 2008 6114 6127
20. T. Clark, M. Hennemann, J.S. Murray, and P. Politzer J. Mol. Model. 13 2007 291 296
21. G. Valerio, G. Raos, S.V. Meille, P. Metrangolo, and G. Resnati J. Phys. Chem. A 104 2000 1617 1620
22. R. Bianchi, A. Forni, and T. Pilati Chem. Eur. J. 9 2003 1631 1638
23. P. Metrangolo, G. Resnati, T. Pilati, and S. Biella P. Metrangolo, G. Resnati, Halogen Bonding Fundamentals and Applications 2008 Springer Berlin 105 136
24. P. Metrangolo, and G. Resnati Chem. Eur. J. 7 2001 2511 2519
25. R.G. Gonnade, M.S. Shashidhar, and M.M. Bhadbhade J. Indian Inst. Sci. 87 2007 149 165
26. H.L. Nguyen, P.N. Horton, M.B. Hursthouse, A.C. Legon, and D.W. Bruce J. Am. Chem. Soc. 126 2004 16 17
27. P. Metrangolo, C. Präsang, G. Resnati, R. Liantonio, A.C. Whitwood, and D.W. Bruce Chem. Commun. 2006 3290 3292
28. V. Mugnaini, C. Punta, R. Liantonio, P. Metrangolo, F. Recupero, G. Resnati, G.F. Pedulli, and M. Lucarini Tetrahedron Lett. 47 2006 3265 3269
29. K. Boubekeur, J.L. Syssa-Magalé, P. Palvadeau, and B. Schöllhorn Tetrahedron Lett. 47 2006 1249 1252
30. E. Cariati, A. Forni, S. Biella, P. Metrangolo, F. Meyer, G. Resnati, S. Righetto, E. Tordin, and R. Ugo Chem. Commun. 2007 2590 2592
31. R. Liantonio, P. Metrangolo, T. Pilati, G. Resnati, and A. Stevenazzi Cryst. Growth Des. 3 2003 799 803
32. D.B. Fox, R. Liantonio, P. Metrangolo, T. Pilati, and G. Resnati J. Fluor. Chem. 125 2004 271 281
33. P. Metrangolo, W. Panzeri, F. Recupero, and G. Resnati J. Fluor. Chem. 114 2002 27 33
34. D.W. Bruce, P. Metrangolo, F. Meyer, C. Präsang, G. Resnati, G. Terraneo, and A.C. Whitwood New J. Chem. 32 2008 477 482
35. G. Gattuso, R. Liantonio, P. Metrangolo, F. Meyer, G. Resnati, A. Pappalardo, M.F. Parisi, T. Pilati, I. Pisagatti, and G. Resnati Supramol. Chem. 18 2006 235 246
36. P. Metrangolo, T. Pilati, G. Terraneo, S. Biella, and G. Resnati CrystEngComm 11 2009 1187 1196
37. A. Bianchi, K. Bowman-James, and E. García-Españaed Supramolecular Chemistry of Anions 1997 Wiley-VCH New York
38. J.L. Sessler, P.A. Gale, and W.S. Cho Anion Receptor Chemistry 2006 Royal Society of Chemistry Cambridge, UK
39. P.A. Gale Coord. Chem. Rev Special Issue: 35 Years of Synthetic Anion Receptor Chemistry, 1968-2003 240 2003 1 226
40. P.A. Gale Coord. Chem. Rev. Special Issue: Anion Coordination Chemistry II 250 2006 2917 3244
41. P. Anzenbacher Jr., R. Nishiyabu, and M.A. Palacios Coord. Chem. Rev. 250 2006 2929 2938
42. J.L. Sessler, and J.M. Davis Acc. Chem. Res. 34 2001 989 997
43. T.K. Chandrashekar, and S. Venkatraman Acc. Chem. Res. 36 2003 676 691
44. R. Misra, and T.K. Chandrashekar Acc. Chem. Res. 41 2008 265 279
45. A.P. Davis Coord. Chem. Rev. 250 2006 2939 2951
46. M.H. Filby, and J.W. Steed Coord. Chem. Rev. 250 2006 3200 3218
47. M.D. Lankshear, and P.D. Beer Acc. Chem. Res. 40 2007 657 668
48. V. Amendola, D. Esteban-Gomez, L. Fabbrizzi, and M. Licchelli Acc. Chem. Res. 39 2006 343 353
49. P.A. Gale Acc. Chem. Res. 39 2006 465 475
50. E. García-Españaed, P. Díaz, J.M. Llinares, and A. Bianchi Coord. Chem. Rev. 250 2006 2952 2986
51. K. Wichmann, B. Antonioli, T. Söhnel, M. Wenzel, K. Gloe, K. Gloe, J.R. Price, L.F. Lindoy, A.J. Blake, and M. Schröder Coord. Chem. Rev. 250 2006 2987 3003
52. E.A. Katayev, Y.A. Ustynyuk, and J.L. Sessler Coord. Chem. Rev. 250 2006 3004 3037
53. C. Schmuck Coord. Chem. Rev. 250 2006 3053 3067
54. E.J. O'Neil, and B.D. Smith Coord. Chem. Rev. 250 2006 3068 3080
55. G. Minguez Espallargas, L. Brammer, J. van de Streek, K. Shankland, A.J. Florence, and H. Adams J. Am. Chem. Soc. 128 2006 9584 9585
56. A. Casnati, G. Cavallo, P. Metrangolo, G. Resnati, F. Ugozzoli, and R. Ungaro Chem. Eur. J. 15 2009 7903 7912
57. R. Liantonio, P. Metrangolo, T. Pilati, and G. Resnati Cryst. Growth Des. 3 2003 355 361
58. R. Liantonio, P. Metrangolo, F. Meyer, T. Pilati, W. Navarrini, and G. Resnati Chem. Commun. 2006 1819 1820
59. S.V. Lindeman, J. Hecht, and J.K. Kochi J. Am. Chem. Soc. 125 2003 11597 11606
60. P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, and G. Terraneo Chem. Commun. 2008 1635 1637
61. P. Metrangolo, Y. Carcenac, M. Lahtinen, T. Pilati, K. Rissanen, A. Vij, and G. Resnati Science 323 2009 1461 1464
62. A. Mele, P. Metrangolo, H. Neukirch, T. Pilati, and G. Resnati J. Am. Chem. Soc. 127 2005 14972 14973
63. M.G. Sarwar, B. Dragisic, S. Sagoo, and M.S. Taylor Angew. Chem. 122 2010 1718 1721
64. A. Abate, S. Biella, G. Cavallo, F. Meyer, H. Neukirch, P. Metrangolo, T. Pilati, G. Resnati, and G. Terraneo J. Fluor. Chem. 130 2009 1171 1177
65. J. Kristin Bowman Acc. Chem. Res. 38 2005 671 678
66. H. Bock, and S. Holl Z. Naturforsch. B: Chem. Sci. 56 2001 152 163
67. A. Casnati, R. Liantonio, P. Metrangolo, G. Resnati, R. Ungaro, and F. Ugozzoli Angew. Chem., Int. Ed. 45 2006 1915 1918
68. G. Gattuso, A. Pappalardo, M.F. Parisi, I. Pisagatti, F. Crea, R. Liantonio, P. Metrangolo, W. Navarrini, G. Resnati, T. Pilati, and S. Pappalardo Tetrahedron 63 2007 4951 4958
69. M. Ghassemzadeh, K. Harms, and K. Dehnicke Chem. Ber. 129 1996 115 120
70. H. Bock, and S. Holl Z. Naturforsch. B: Chem. Sci. 57 2002 843 858
71. H.M. Yamamoto, J.I. Yamaura, and R. Kato J. Am. Chem. Soc. 120 1998 5905 5913
72. S.V. Rosokha, I.S. Neretin, T.Y. Rosokha, J. Hecht, and J.K. Kochi Heteroatom Chem. 17 2006 449 459
73. T. Nakamoto, Q. Wang, Y. Miyazaki, and M. Sorai Polyhedron 21 2002 1299 1304
74. A. Bondi J. Phys. Chem. 68 1964 441 451
75. All the formed networks in co-crystals 3-5, 8, and 9 were analyzed with the software Topos 4.0 by V.A. Blatov, IUCr CompComm. Newsletter 2006, 7, 4; see also http://www.topos.ssu.samara.ru.
76. For a tutorial on interpenetration modes, please have a look at http://www.chem.monash.edu.au/staff/sbatten/interpen/index.html.