Synthesis and properties of new functionalized guanidinium based ionic liquids as non-toxic versatile organic materials

Tetrahedron

Volumn 66, Issue 45, 2010, Pages 8785-8794

  Carrera, Gonalo V S M ^a,b   Frade, Raquel F M ^b   Aires De Sousa, João ^a   Afonso, Carlos A M ^b   Branco, Luis C ^a  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

Guanidium; Interfacial properties; Ionic liquid; Organic materials; Toxicity

Indexed keywords

DIMETHYL GUANIDINIUM; GLASS; GUANIDINE DERIVATIVE; IONIC LIQUID; N.N DIMETHYL N',N'' DIETHYL N',N'' BIS(2,3 DIBROMO 2 METHYLPROPYL) GUANIDINIUM BIS(TRIFLUOROMETHANOSULFONYL)IMIDE; N.N DIMETHYL N',N',N'',N'' TETRAKIS(2,3 DIBROMO 2 METHYLPROPYL) GUANIDINIUM BIS(TRIFLUOROMETHANOSULFONYL)IMIDE; N.N DIMETHYL N',N',N'',N'' TETRAKIS(2,3 DIBROMOPROPIL) GUANIDINIUM BIS(TRIFLUOROMETHANOSULFONYL)IMIDE; N.N DIMETHYL N',N',N'',N'' TETRAKIS(2,3 DIBROMOPROPYL) GUANIDINIUM HEXAFLUOROPHOSPHATE; ORGANIC COMPOUND; POLITEF; TRI HEXYL TETRA DECYLPHOSPHONIUM; TRI OCTYL METHYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN CACO 2; COLON CARCINOMA; CONTACT ANGLE; DENSITY; GLASS TRANSITION TEMPERATURE; HUMAN; HUMAN CELL; MELTING POINT; MISCIBILITY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SURFACE TENSION; SYNTHESIS;

EID: 77957998361     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.08.040     Document Type: Article

References (83)

1. T. Welton Chem. Rev. 99 1999 2071 2084
2. J. Dupont, R.F. de Souza, and P.A.Z. Suarez Chem. Rev. 102 2002 3667 3691
3. R. Sheldon Chem. Commun. 2001 2399 2407
4. R.D. Rogers, and K.R. Seddon Ionic Liquids as Green Solvents: Progress and Prospects 2003 American Chemical Society Washington, DC
5. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis 1st ed. 2002 Wiley-VCH Weinheim
6. A.R. Katritzky, R. Jain, A. Lomaka, R. Petrukhin, M. Karelson, A.E. Visser, and R.D. Rogers J. Chem. Inf. Comput. Sci. 42 2002 225 231
7. G. Carrera, and J. Aires-de-Sousa Green Chem. 7 2005 20 27
8. G.V.S.M. Carrera, L.C. Branco, J. Aires-de-Sousa, and C.A.M. Afonso Tetrahedron 64 2008 2216 2224
9. A. Varnek, N. Kireeva, I.V. Tetko, I.I. Baskin, and V.P. Solov'ev J. Chem. Inf. Model. 47 2007 1111 1122
10. D.M. Eike, J.F. Brennecke, and E.J. Maginn Green Chem. 5 2003 323 328
11. J. Palomar, V.R. Ferro, J.S. Torrecilla, and F. Rodríguez Ind. Eng. Chem. Res. 46 2007 6041 6048
12. R.L. Gardas, and J.A.P. Coutinho Fluid Phase Equilib. 265 2008 57 65
13. J. Dupont, and P.A.Z. Suarez Phys. Chem. Chem. Phys. 8 2006 2441 2452
14. R.A. Sheldon, R.M. Lau, M.J. Sorgedrager, F. van Rantwijk, and K.R. Seddon Green Chem. 4 2002 147 151
15. F. Van Rantwijk, and R.A. Sheldon Chem. Rev. 107 2007 2757 2785
16. R. Sheldon Chem. Commun. 2001 2399 2407
17. C. Chiappe, and D. Pieraccini J. Phys. Org. Chem. 18 2005 275 297
18. M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta, and H.G. Bonacorso Chem. Rev. 108 2008 2015 2050
19. H. Zhao Chem. Eng. Commun. 193 2006 1660 1677 and references therein
20. S.A. Shamsi, and N.D. Danielson J. Sep. Sci. 30 2007 1729 1750
21. L.C. Branco, J.G. Crespo, and C.A.M. Afonso Angew. Chem., Int. Ed. 41 2002 2771 2773
22. L.C. Branco, J.G. Crespo, and C.A.M. Afonso Chem. - Eur. J. 8 2002 3865 3871
23. J.E. Bara, T.K. Carlisle, C.J. Gabriel, D. Camper, A. Finotello, D.L. Gin, and R.D. Noble Ind. Eng. Chem. Res. 48 2009 2739 2751
24. B. Wang, J. Lin, F. Wu, and Y. Peng Ind. Eng. Chem. Res. 47 2008 8355 8360
25. M. Antonietti, D. Kuang, B. Smarsly, and Y. Zhou Angew. Chem., Int. Ed. 43 2004 4988 4992
26. Z. Fei, D. Kuang, D. Zhao, C. Klein, W. Han Ang, S.M. Zakkeruddin, M. Gratzel, and P. Dyson Inorg. Chem. 45 2006 10407 10409
27. D. Kuang, P. Walter, F. Nuesch, S. Kim, J. Ko, P. Comte, S.M. Zakkeruddin, M.K. Nazeeruddin, and M. Gratzel Langmuir 23 2007 10906 10909
28. H. Zhao, S. Xia, and P. Ma J. Chem. Technol. Biotechnol. 80 2005 1089 1096
29. Y. Mochizuki, and K. Sugawara Energy Fuels 22 2008 3303 3307
30. N. Papaiconomou, J.-M. Lee, J. Salminen, M. von Stosch, and J.M. Prausnitz Ind. Eng. Chem. Res. 47 2008 5080 5086
31. N.M.M. Mateus, L.C. Branco, N.M.T. Loureno, and C.A.M. Afonso Green Chem. 5 2003 347 352
32. H. Kunkel, and G. Maas Eur. J. Org. Chem. 2007 3746 3757
33. S. Li, Y. Lin, H. Xie, S. Zhang, and J. Xu Org. Lett. 8 2006 391 394
34. H. Xie, S. Zhang, and H. Duan Tetrahedron Lett. 45 2004 2013 2015
35. H. Xie, H. Duan, S. Li, and S. Zhang New J. Chem. 29 2005 1199 1203
36. A. Zhu, T. Jiang, H. Buxing, J. Huang, J. Zhang, and X. Ma New J. Chem. 30 2006 736 740
37. X. Xin, X. Guo, H. Duan, Y. Lin, and H. Sun Catal. Commun. 8 2007 115 117 and references therein cited
38. T. Ishikawa, and T. Kumamonto Synthesis 2006 737 752
39. L.C. Branco, and C.A.M. Afonso J. Org. Chem. 69 2004 4381 4389
40. L.C. Branco, F.C. Ferreira, and J.L. Santos Adv. Synth. Catal. 350 2008 2086 2098
41. P. Wang, S.M. Zakeeruddin, M. Grätzel, W. Kantlehner, J. Mezger, E.V. Stoyanov, and O. Scherr Appl. Phys. A 79 2004 73 77
42. L.C. Branco, J.N. Rosa, J.J.M. Ramos, and C.A.M. Afonso Chem. - Eur. J. 8 2002 3671 3677
43. J.D. Holbrey, A.E. Visser, S.K. Spear, W.M. Reichert, R.P. Swatloski, G.A. Broker, and R.D. Rogers Green Chem. 5 2003 129 135
44. A.K. Prasad, V. Kumar, S. Malhotra, V.T. Ravikumar, Y.S. Sanghvi, and V.S. Parmar Bioorg. Med. Chem. 13 2005 4467 4472
45. J. Pernak, K. Sobaszkiewicz, and I. Mirska Green Chem. 5 2003 52 56
46. H. Xue, and J.M. Shreeve Eur. J. Inorg. Chem. 2005 2573 2580
47. T.L. Merrigan, E.D. Bates, S.C. Dorman, and J.H. Davis Jr. Chem. Commun. 2000 2051 2052
48. P. Wasserscheid, B. Drießen-Hülscher, R. van Hal, H.C. Steffens, and J. Zimmermann Chem. Commun. 2003 2038 2039
49. D. Zhao, Z. Fei, R. Scopelliti, and P.J. Dyson Inorg. Chem. 43 2004 2197 2205
50. E.D. Bates, R.D. Mayton, I. Ntai, and J.H. Davis Jr. J. Am. Chem. Soc. 124 2002 926 927
51. M.D. Soutullo, C.I. Odom, B.F. Wicker, C.N. Henderson, A.C. Stenson, and J.H. Davis Jr. Chem. Mater. 19 2007 3581 3583
52. M.T. Garcia, N. Gathergood, and P.J. Scammells Green Chem. 7 2005 9 14
53. Q. Liu, M.H.A. Janssen, F. van Rantwijk, and R. Sheldon Green Chem. 7 2005 39 42
54. A.A. Rosatella, L.C. Branco, and C.A.M. Afonso Green Chem. 11 2009 1406 1413
55. L.C. Branco, P.M.P. Gois, N.M.T. Loureno, V.B. Kurteva, and C.A.M. Afonso Chem. Commun. 2006 2371 2372
56. K. Fukumoto, M. Yoshizawa, and H. Ohno J. Am. Chem. Soc. 127 2005 2398 2399
57. C. Ye, and J.M. Shreeve J. Org. Chem. 69 2004 6511 6513
58. C. Ye, and J.M. Shreeve J. Phys. Chem. A 111 2007 1456 1461
59. M. Deetlefs, K.R. Seddon, and M. Shara Phys. Chem. Chem. Phys. 8 2006 642 649
60. G. Law, and P.R. Watson Langmuir 17 2001 6138 6141
61. P. Kilaru, G.A. Baker, and P. Scovazzo J. Chem. Eng. Data 52 2007 2306 2314
62. M.G. Freire, P.J. Carvalho, A.M. Fernandes, I.M. Marrucho, A.J. Queimada, and J.A.P. Coutinho J. Colloid Interface Sci. 314 2007 621 630
63. G.V.S.M. Carrera, C.A.M. Afonso, and L.C. Branco J. Chem. Eng. Data 55 2010 609 615
64. L. Gao, and T.J. McCarthy J. Am. Chem. Soc. 129 2007 3804 3805
65. B.S. Lee, Y.S. Chi, J.K. Lee, I.S. Choi, C.E. Song, S.K. Namgoong, and S. Lee J. Am. Chem. Soc. 126 2004 480 481
66. Y. Zhao, M. Li, and Q. Lu Langmuir 24 2008 3937 3943
67. R. Ferreira, M. Blesic, J. Trindade, I. Marrucho, J.N.C. Lopes, and L.P.N. Rebelo Green Chem. 10 2008 918 928
68. S. Millefiorini, A.H. Tkaczyc, R. Sedev, J. Efhimiadis, and J. Ralston J. Am. Chem. Soc. 128 2006 3098 3101
69. T. Schlama, V. Gouverneur, A. Valleix, A. Greiner, L. Toupet, and C. Mioskowski J. Org. Chem. 62 1997 4200 4202
70. All around ionic liquids: http://98.131.55.98/ accessed at 21/02/2010
71. P.S. Kulkarni, L.C. Branco, J.G. Crespo, M.C. Nunes, A. Raymundo, and C.A.M. Afonso Chem. - Eur. J. 13 2007 8478 8488
72. Ohno, H.; Mizumo, T.; Yoshida, M.; Suga, T. Novel imidazolium compound, EP1721900, 2006.
73. S. Lee, J.-S. Park, and T.R. Lee Langmuir 24 2008 4817 4826
74. D. Janssen, R. De Palma, S. Verlaak, P. Heremans, and W. Dehaen Thin Solid Films 515 2006 1433 1438
75. M.H. Ghatee, and A.R. Zolghadr Fluid Phase Equilib. 263 2008 168 175
76. W. Martino, J.F. de la Mora, Y. Yoshida, G. Saito, and J. Wilkes Green Chem. 8 2006 390 398
77. A. Wandschneider, J.K. Lehmann, and A. Heintz J. Chem. Eng. Data 53 2008 596 599
78. A.A. Freitas, F.H. Quina, and F.A. Carroll J. Phys. Chem. B 101 1997 7488 7493
79. B. Janczuk, A. Zdziennicka, and W. Wojcik Eur. Polym. J. 7 1997 1093 1098 (20 °C)
80. http://www.sigmaaldrich.com/ (20 °C)
81. C. Jumarie, and C. Malo J. Cell. Physiol. 149 1991 24 33
82. R.F.M. Frade, A.A. Rosatella, C.S. Marques, L.C. Branco, P.S. Kulkarni, N.M.M. Mateus, C.A.M. Afonso, and C.M.M. Duarte Green Chem. 11 2009 1660 1665
83. R.F.M. Frade, A. Matias, L.C. Branco, C.A.M. Afonso, and C.M.M. Duarte Green Chem. 9 2007 873 877