Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Ionic Liquids with Solvatochromatic and Charge-Transfer Functionalities Incorporating the Viologen Moiety*

H. Q. Nimal Gunaratne A B , Peter Nockemann A , Sonia Olejarz A , Stephanie M. Reid A , Kenneth R. Seddon A and Geetha Srinivasan A
+ Author Affiliations
- Author Affiliations

A QUILL Centre, School of Chemistry and Chemical Engineering, The Queen’s University of Belfast, Belfast BT9 5AG, UK.

B Corresponding author. Email: n.gunaratne@qub.ac.uk

Australian Journal of Chemistry 66(5) 607-611 https://doi.org/10.1071/CH13054
Submitted: 29 January 2013  Accepted: 22 March 2013   Published: 9 May 2013

Abstract

The synthesis of oligoether-functionalised viologen-based dicationic ionic liquids, their electrochemical properties, solvatochromism, and ability to form charge-transfer complexes, are described.


References

[1]  (a) A. E. Visser, R. P. Swatloski, W. M. Reichert, R. Mayton, S. Sheff, A. Wierzbicki, J. H. Davis, R. D. Rogers, Chem. Commun. 2001, 135.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXotFWr&md5=72e4823a921392baef98c598ddaed9b8CAS |
      (b) J. H. Davis, Chem. Lett. 2004, 33, 1072.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) P. Nockemann, B. Thijs, T. N. Parac-Vogt, K. Van Hecke, L. Van Meervelt, B. Tinant, I. Hartenbach, T. Schleid, V. T. Ngan, M. T. Nguyen, K. Binnemans, Inorg. Chem. 2008, 47, 9987.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) R. Giernoth, Angew. Chem. Int. Ed. 2010, 49, 2834.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) M. Deetlefs, K. R. Seddon, Chim. Oggi 2006, 24, 16.
      (f) D. R. MacFarlane, K. R. Seddon, Aust. J. Chem. 2007, 60, 3.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) S. A. Forsyth, U. Frohlich, P. Goodrich, H. Q. N. Gunaratne, C. Hardacre, A. McKeown, K. R. Seddon, New J. Chem. 2010, 34, 723.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) P. Costantini, V. Petroililli, R. Colonna, P. Bernardi, Toxicology 1995, 99, 77.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXls12nu70%3D&md5=c6f1660b78daee33e415c5cc3d7271b8CAS | 7539163PubMed |
      (b) T. R. Roberts, J. S. Dyson, M. C. G. Lane, J. Agric. Food Chem. 2002, 50, 362.
      (c) A. B. Manning-Bog, A. L. McCormack, J. Li, V. N. Uversky, A. L. Fink, D. A. Di Mont, J. Biol. Chem. 2002, 277, 1641.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. W. Kitzler, H. Minakani, I. Frivodich, J. Bacteriol. 1990, 172, 686.

[3]  (a) T. W. Ebbesen, O. Ferraud, J. Phys. Chem. 1983, 87, 3717.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXltFels7c%3D&md5=479fcba7b7b26f42ca11beb5e4fc42f4CAS |
      (b) R. D. Small, J. C. Scaian, J. Phys. Chem. 1977, 61, 197.

[4]  (a) C. R. Bock, T. J. Meyer, D. G. Whitten, J. Am. Chem. Soc. 1974, 96, 4710.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2cXltVCgtr4%3D&md5=d7cd4d00baa7cf00c27220a1d2488138CAS |
      (b) P.-A. Brugget, M. Grätzel, J. Am. Chem. Soc. 1980, 102, 2461.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. Int. Ed. 1989, 28, 1396.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) M. Liu, S. Li, M. Hu, F. Wang, F. Huang, Org. Lett. 2010, 12, 760.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) O. S. Miljanic, W. R. Dichtel, S. Mortezaei, J. F. Stoddart, Org. Lett. 2006, 8, 4835.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) K. Patel, O. S. Miljanic, J. F. Stoddart, Chem. Commun. 2008, 1853.

[6]  (a) G. Cooke, L. M. Daniel, F. Cazier, J. F. Garety, S. G. Hewage, A. Parkin, G. Rabani, V. M. Rotello, C. C. Wilson, P. Woisel, Tetrahedron 2007, 63, 11114.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtFSisLnF&md5=7700fbf17f6319c48a8ac262132f055dCAS |
      (b) S. K. Dey, A. Coskun, A. C. Fahrenbach, G. Barin, A. N. Basuray, A. Trabolsi, Y. Y. Botros, J. F. Stoddart, Chem. Sci. 2011, 2, 1046.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) S. Li, K. Zhu, B. Zheng, X. Wen, N. Li, F. Huang, Eur. J. Org. Chem. 2009, 1053.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) X. Guo, Y. Zhou, M. Feng, Y. Xu, D. Zhang, H. Gao, Q. Fan, D. Zh, Adv. Funct. Mater. 2007, 17, 763.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  (a) I. Tabushi, K. Yamamura, K. Kominami, J. Am. Chem. Soc. 1986, 108, 6409.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XlsVCitLk%3D&md5=20b11ff2f4ebf04c11fa24e0c4a78a22CAS |
      (b) L. Chen, D. W. McBranch, H.-L. Wang, R. Helgeson, F. Wudl, D. G. Whitten, Proc. Natl. Acad. Sci. USA 1999, 96, 12287.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) L. Chen, S. Xu, D. McBranch, D. Whitten, J. Am. Chem. Soc. 2000, 122, 9302.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  A. F. Kapustinskii, Q. Rev. 1956, 10, 283.
         | 1:CAS:528:DyaG2sXislI%3D&md5=d2914bae2b76ed60e49b12ef3219f397CAS |

[9]  (a) Y. X. Shen, P. T. Engen, M. A. G. Berg, J. S. Merola, H. W. Gibson, Macromolecules 1992, 25, 2786.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XisFKjurs%3D&md5=2ca9e1298d957a54fa34fd4620d09682CAS |
      (b) J. L. Anderson, R. Ding, A. Ellern, D. W. Armstrong, J. Am. Chem. Soc. 2005, 127, 593.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) Z. Zeng, B. S. Phillips, J.-C. Xiao, J. M. Shreeve, Chem. Mater. 2008, 20, 2719.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. D. Holbrey, A. E. Visser, S. K. Spear, W. M. Reichert, R. P. Swatloski, G. A. Broker, R. D. Rogers, Green Chem. 2003, 5, 129.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) K. R. J. Lovelock, A. Deyko, J. Corfield, P. N. Gooden, P. Licence, R. G. Jones, ChemPhysChem 2009, 10, 337.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  S. J. Coles, P. A. Gale, Chem. Sci. 2012, 3, 683.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhslOqs7k%3D&md5=4f007bdc1d0d245dec6228dab75cb4ceCAS |

[11]  (a) E. M. Kosower, J. Am. Chem. Soc. 1958, 80, 3253.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG1MXhsFSjsQ%3D%3D&md5=e4ace96829b4dd55b9a23b5363c52b1cCAS |
      (b) E. M. Kosower, J. A. Skorcz, W. M. Schwarz, J. W. Patton, J. Am. Chem. Soc. 1960, 82, 2188.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  (a) K. Dimroth, C. Reichardt, T. Siepmann, F. Bohlmann, Liebigs Ann. Chem. 1963, 661, 1.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF3sXksVahsro%3D&md5=31c85ae0424e89fb8953c46cc49f6362CAS |
      (b) C. Reichardt, Justus Liebigs Ann. Chem. 1971, 752, 64.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) C. Reichardt, Chem. Rev. 1994, 94, 2319.
         | Crossref | GoogleScholarGoogle Scholar |
         (d) C. Reichardt, T. Welton, Solvents and Solvent Effects in Organic Chemistry 2011, 4th edn, Ch. 6 and 7 (Wiley-VCH: Weinheim).
      (e) S. Nigam, S. Rutan, Appl. Spectrosc. 2001, 55, 362.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  (a) J. Ferraris, D. O. Cowan, V. Walatka, J. H. Perlstein, J. Am. Chem. Soc. 1973, 95, 948.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXpslGhug%3D%3D&md5=c62f10a5f5dbf91c5b8517fce8bb0027CAS |
      (b) M. Fourmigue, K. Boubekeur, P. Batail, J. Renouard, G. Jacob, New J. Chem. 1998, 22, 845.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) T. Enoki, A. Miyazaki, Chem. Rev. 2004, 104, 5449.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) D. L. Lichtenberger, R. L. Johnston, K. Hinkelmann, T. Suzuki, F. Wudl, J. Am. Chem. Soc. 1990, 112, 3302.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  (a) N. Christinat, R. Scopelliti, K. Severin, Chem. Commun. 2008, 3660.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXptVKmu70%3D&md5=f244229f4e12522c3c602c01a2b6d267CAS |
      (b) H. W. Gibson, H. Wang, C. Slebodnick, J. Merola, W. S. Kassel, A. L. Rheingold, J. Org. Chem. 2007, 72, 3381.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) J. F. Stoddart, H. M. Colquhoun, Tetrahedron 2008, 64, 8231.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) T. B. Gasa, J. M. Spruell, W. R. Dichtel, T. J. Sørensen, D. Philp, J. F. Stoddart, P. Kuzmic, Chem. – Eur. J. 2009, 15, 106.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  (a) A. P. Abbott, G. Capper, D. L. Davies, R. K. Rasheed, V. Tambyrajah, Chem. Commun. 2003, 70.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXit1egsg%3D%3D&md5=8568979badcdec9695885abdce77295eCAS |
      (b) A. P. Abbott, D. Boothby, G. Capper, D. L. Davies, R. K. Rasheed, J. Am. Chem. Soc. 2004, 126, 9142.
         | Crossref | GoogleScholarGoogle Scholar |