Molecular networks based on dative boron-nitrogen bonds

Angewandte Chemie - International Edition

Volumn 50, Issue 13, 2011, Pages 3034-3037

  Sheepwash, Erin ^a   Krampl, Vincent ^a   Scopelliti, Rosario ^a   Sereda, Olha ^b   Neels, Antonia ^b   Severin, Kay ^a  

^a EPFL   (Switzerland)

^b CSEM   (Switzerland)

Author keywords

Boron; Crystal engineering; Dynamic covalent chemistry; Networks; Self assembly

Indexed keywords

BIPYRIDYL; CHEMICAL EQUATIONS; DYNAMIC COVALENT CHEMISTRY; MOLECULAR NETWORKS; NETWORKS; NITROGEN BONDS; THREE COMPONENT REACTIONS;

BORON; CRYSTAL ENGINEERING; PHENOLS; SELF ASSEMBLY;

BORON COMPOUNDS;

2,2' BIPYRIDINE; BORANE DERIVATIVE; BORON; BORONIC ACID DERIVATIVE; ESTER; NITROGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GEL; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

2,2'-DIPYRIDYL; BORANES; BORON; BORONIC ACIDS; CRYSTALLOGRAPHY, X-RAY; ESTERS; GELS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITROGEN;

EID: 79952667999     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201007225     Document Type: Article

References (71)

1. a) C. B. Aakeröy, N. R. Champness, C. Janiak, CrystEngComm 2010, 12, 22-43;
2. b) G. R. Desiraju, Angew. Chem. 2007, 119, 8492-8508;
3. Angew. Chem. Int. Ed. 2007, 46, 8342-8356;
4. c) D. Braga, L. Brammer, N. R. Champness, CrystEngComm 2005, 7, 1-19;
5. d) B. Moulton, M. J. Zaworotko, Chem. Rev. 2001, 101, 1629-1658.
6. a) M. D.Ward, Struct. Bonding (Berlin) 2009, 132, 1-23;
7. b) I. A. Baburin, V. A. Blatov, L. Carlucci, G. Ciani, D. M. Proserpio, Cryst. Growth Des. 2008, 8, 519-539;
8. c) K. E. Maly, N. Malek, J.-H. Fournier, P. Rodríguez-Cuamatzi, T. Maris, J. D. Wuest, Pure Appl. Chem. 2006, 78, 1305-1321;
9. d) G. R. Desiraju, Acc. Chem. Res. 2002, 35, 565-573.
10. C. Janiak, J. K. Vieth, New J. Chem. 2010, 34, 2366-2388, and references therein.
11. a) M. Fourmigué, Curr. Opin. Solid State Mater. Sci. 2009, 13, 36-45;
12. b) P. Metrangolo, T. Pilati, G. Terraneo, S. Biella, G. Resnati, CrystEngComm 2009, 11, 1187-1196;
13. c) L. Brammer, G. M. Espallargas, S. Libri, CrystEngComm 2008, 10, 1712-1727;
14. d) P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, G. Terraneo, Angew. Chem. 2008, 120, 6206-6220;
15. Angew. Chem. Int. Ed. 2008, 47, 6114-6127.
16. M. J. Katz, K. Sakai, D. B. Leznoff, Chem. Soc. Rev. 2008, 37, 1884-1895.
17. M. Nishio, CrystEngComm 2004, 6, 130-158.
18. C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669.
19. a) A. Dawn, T. Shiraki, S. Haraguchi, S.-i. Tamaru, S. Shinkai, Chem. Asian J. 2011, 6, 266-282;
20. b) A. Ajayaghosh, V. K. Praveen, C. Vijayakumar, Chem. Soc. Rev. 2008, 37, 109-122;
21. c) A. R. Hirst, B. Escuder, J. F. Miravet, D. K. Smith, Angew. Chem. 2008, 120, 8122-8139;
22. Angew. Chem. Int. Ed. 2008, 47, 8002-8018;
23. d) M. George, R. G. Weiss, Acc. Chem. Res. 2006, 39, 489-497;
24. e) N. M. Sangeetha, U. Maitra, Chem. Soc. Rev. 2005, 34, 821-836;
25. f) X. Y. Liu, Top. Curr. Chem. 2005, 256, 1-37;
26. g) P. Terech, R. G. Weiss, Chem. Rev. 1997, 97, 3133-3159.
27. G. R. Desiraju, Angew. Chem. 1995, 107, 2541-2558;
28. Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327;.
29. a) J. H. van Esch, Langmuir 2009, 25, 8392-8394;
30. b) P. Dastidar, Chem. Soc. Rev. 2008, 37, 2699-2715.
31. H. Höpfl, J. Organomet. Chem. 1999, 581, 129-149.
32. a) B. E. Collins, S. Sorey, A. E. Hargrove, S. H. Shabbir, V. M. Lynch, E. V. Anslyn, J. Org. Chem. 2009, 74, 4055-4060;
33. b) L. Zhu, S. H. Shabbir,M. Gray, V. M. Lynch, S. Sorey, E. V. Anslyn, J. Am. Chem. Soc. 2006, 128, 1222-1232;
34. c) W. Ni, G. Kaur, G. Springsteen, B. Wang, S. Franzen, Bioorg. Chem. 2004, 32, 571-581.
35. a) R. Nishiyabu, Y. Kubo, T. D. James, J. S. Fossey, Chem. Commun. 2011, 47, 1124-1150;
36. b) A. L. Korich, P. M. Iovine, Dalton Trans. 2010, 39, 1423-1431;
37. c) F. Jäkle, Chem. Rev. 2010, 110, 3985-4022;
38. d) K. Severin, Dalton Trans. 2009, 5253-5264;
39. e) N. Fujita, S. Shinkai, T. D. James, Chem. Asian J. 2008, 3, 1076-1091.
40. a) N. Christinat, R. Scopelliti, K. Severin, J. Org. Chem. 2007, 72, 2192-2200;
41. b) N. Christinat, R. Scopelliti, K. Severin, Chem. Commun. 2004, 1158-1159.
42. N. Christinat, E. Croisier, R. Scopelliti, M. Cascella, U. Röthlisberger, K. Severin, Eur. J. Inorg. Chem. 2007, 5177-5181.
43. For one-dimensional polymers featuring dative B-N bonds between boranes and N-donor ligands, see: a) Y. Qin, C. Cui, F. Jäkle, Macromolecules 2007, 40, 1413-1420;
44. b) R. E. Dinnebier, M. Wagner, F. Peters, K. Shankland, W. I. F. David, Z. Anorg. Allg. Chem. 2000, 626, 1400-1405;
45. c) M. Grosche, E. Herdtweck, F. Peters, M. Wagner, Organometallics 1999, 18, 4669-4672;
46. d) M. Fontani, F. Peters, W. Scherer, W. Wachter, M. Wagner, P. Zanello, Eur. J. Inorg. Chem. 1998, 1453-1465.
47. 4-tert-Butylcatechol was used instead of simple catechol to increase solubility.
48. The color is likely due to charge-transfer transitions from the electron-rich catecholate to the electron-deficient bipyridyl linkers (see Ref. [14]).
49. N. Farfán, R. Contreras, J. Chem. Soc. Perkin Trans. 2 1987, 771-773.
50. -3. For both structures, scattering contributions from diffuse solvent were removed using the SQUEEZE routine in PLATON (see the Supporting Information). CCDC 800644 (2) and 800645 (3) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
51. For COFs with boronate ester linkages, see: a) E. L. Spitler, W. R. Dichtel, Nat. Chem. 2010, 2, 672-677;
52. b) S.Wan, J. Guo, J. Kim, H. Ihee, D. Jiang, Angew. Chem. 2008, 120, 8958-8962;
53. Angew. Chem. Int. Ed. 2008, 47, 8826-8830;
54. c)W. R. Tilford, S. J. Mugavero III, P. J. Pellechia, J. J. Lavigne, Adv. Mater. 2008, 20, 2741-2746;
55. d) N. A. A. Zwaneveld, R. Pawlak, M. Abel, D. Catalin, D. Gigmes, D. Bertin, L. Porte, J. Am. Chem. Soc. 2008, 130, 6678-6679;
56. e) H. M. El-Kaderi, J. R. Hunt, J. L. Mendoza-Cortés, A. P. Côté, R. E. Taylor, M. O'Keeffe, O. M. Yaghi, Science 2007, 316, 268-272;
57. f) R.W. Tilford,W. R. Gemmill, H.-C. zur Loye, J. J. Lavigne, Chem. Mater. 2006, 18, 5296-5301.
58. W. Clegg, A. J. Scott, F. E. S. Souza, T. B. Marder, Acta Crystallogr. Sect. C 1999, 55, 1885-1888.
59. For a discussion of catenation in metal-organic frameworks, see: O. K. Farha, C. D. Malliakas,M. G. Kanatzidis, J. T. Hupp, J. Am. Chem. Soc. 2010, 132, 950-952.
60. For examples, see: a) Y. Li, J. Liu, G. Du, H. Yan, H. Wang, H. Zhang,W. An,W. Zhao, T. Sun, F. Xin, L. Kong, Y. Li, A. Hao, J. Hao, J. Phys. Chem. B 2010, 114, 10321-10326;
61. b) D. G. Velázquez, D. D. Díaz, Á. G. Ravelo, J. J. M. Tellado, J. Am. Chem. Soc. 2008, 130, 7967-7973;
62. c) B. Jonganurakkun, Y. Nodasaka, N. Sakairi, N. Nishi, Macromol. Biosci. 2006, 6, 99-103;
63. d) S. H. Um, J. B. Lee, N. Park, S. Y. Kwon, C. C. Umbach, D. Luo, Nat. Mater. 2006, 5, 797-801;
64. e) W. Weng, J. B. Beck, A. M. Jamieson, S. J. Rowen, J. Am. Chem. Soc. 2006, 128, 11663-11672;
65. f) S. J. Rowan, J. B. Beck, Faraday Discuss. 2005, 128, 43-53;
66. g) Y. Zhao, J. B. Beck, S. J. Rowan, A. M. Jamieson, Macromolecules 2004, 37, 3529-3531;
67. h) J. B. Beck, S. J. Rowan, J. Am. Chem. Soc. 2003, 125, 13922-13923.
68. For a review on two-component gels, see: A. R. Hirst, D. K. Smith, Chem. Eur. J. 2005, 11, 5496-5508.
69. K. Murata, M. Aoki, T. Suzuki, T. Harada, H. Kawabata, T. Komori, F. Ohseto, K. Ueda, S. Shinkai, J. Am. Chem. Soc. 1994, 116, 6664-6676.
70. B. Xing, M.-F. Choi, B. Xu, Chem. Eur. J. 2002, 8, 5028-5032.
71. Preliminary results show that the stability constants of boronate ester-pyridyl interactions can be altered by more than three orders of magnitude using electronic effects.