Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Multi-Electron Donor Organic Molecules Containing Hydroquinone Methyl-Ether as Redox Active Units

  • Khandelwal, Manish (Department of Chemistry, Florida Institute of Technology) ;
  • Hwang, In-Chul (Center for Superfunctional Materials, Department of Chemistry, Pohang University of Science and Technology) ;
  • Nair, Prakash Chandran R. (Amrita School of Biotechnology, Amrita Viswa Vidyapeetham University) ;
  • Lee, Jung-Woo (Center for Superfunctional Materials, Department of Chemistry, Pohang University of Science and Technology)
  • Received : 2011.12.07
  • Accepted : 2012.01.02
  • Published : 2012.04.20
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Abstract

Three hydroquinone dimethyl ether derivatives have been synthesized and characterized by X-ray diffraction. The electron donating properties were evaluated by using UV-vis spectroscopy, cyclic voltammetry and by ESR spectroscopy. The microcrystalline cation-radical salts of the three donor molecules were also isolated by using antimony pentachloride, a single electron Lewis acid oxidant.

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References

  1. Philp, D.; Stoddart, J. F. Angew. Chem. Int. Ed. 1996, 35, 1154. https://doi.org/10.1002/anie.199611541
  2. Balzani, V.; Campagna, S.; Denti, G.; Juris, A.; Serroni, S.;Venturi, M. Acc. Chem. Res. 1998, 31, 26. https://doi.org/10.1021/ar950202d
  3. Reichert, V. R.; Mathias, L. J. Macromolecules 1994, 27, 7015. https://doi.org/10.1021/ma00102a002
  4. Kim, K. S.; Suh, S. B.; Kim, J. C.; Hong, B. H.; Lee, E. C.; Yun, S.; Tarakeshwar, P.; Lee, J. Y.; Kim, Y.; Ihm, H.; Kim, H. G.; Lee, J. W.; Kim, J. K.; Lee, H. M.; Kim, D.; Cui, C.; Youn, S. J.; Chung, H. Y.; Choi, H. S.; Lee, C.-W.; Cho, S. J.; Jeong, S.; Cho, J.-H J. Am. Chem. Soc. 2002, 124, 14268. https://doi.org/10.1021/ja0259786
  5. Pollak, K. W.; Leon, J. W.; Frechet, J. M. J.; Maskus, M.; Abruna, H. D. Chem. Mater. 1998, 10, 30. https://doi.org/10.1021/cm970312+
  6. Gorman, C. B. Adv. Mater. 1997, 9, 1107.
  7. Wilson, L. M.; Griffin, A. C. J. Mater. Chem. 1993, 3, 991. https://doi.org/10.1039/jm9930300991
  8. Kim, H. G.; Lee, C. W.; Yun, S.; Hong, B. H.; Kim, Y.-O.; Kim, D.; Ihm, H.; Lee, J. W.; Lee, E. C.; Tarakeshwar, P.; Park, S. M.; Kim, K. S. Org. Lett. 2002, 4, 3971. https://doi.org/10.1021/ol0268541
  9. Hong, B. H.; Lee, J. Y.; Lee, C.-W.; Kim, J. C.; Kim, K. S. J. Am. Chem. Soc. 2001, 123, 43, 10748. https://doi.org/10.1021/ja016526g
  10. Hong, B. H.; Bae, S. C.; Lee, C.-W.; Jeong, S.; Kim, K. S. Science 2001, 294, 348. https://doi.org/10.1126/science.1062126
  11. Keegstra, M. A.; Feyter, S. D.; Schryver, F. C. D.; Mullen, K. Angew. Chem. Int. Ed. 1996, 35, 774. https://doi.org/10.1002/anie.199607741
  12. Oldham, W. J., Jr.; Lachicotte, R. J.; Bazan, G. C. J. Am. Chem. Soc. 1998, 120, 2987. https://doi.org/10.1021/ja974209x
  13. Wang, S.; Oldham, W. J., Jr.; Hudack, R. A., Jr.; Bazan, G. C. J. Am. Chem. Soc. 2000, 24, 5695
  14. Yoon, J.; Kim, S. K.; Singh, N. J.; Kim, K. S. Chem. Soc. Rev. 2006, 35, 355. https://doi.org/10.1039/b513733k
  15. Chellappan, K.; Singh, N. J.; Hwang, I.-C.; Lee, J. W.; Kim K. S. Angew. Chem. Int. Ed. 2005, 44, 2899, https://doi.org/10.1002/anie.200500119
  16. Chellappan, K.; Singh, N. J.; Hwang, I.-C.; Lee, J. W.; Kim K. S. Angew. Chem. 2005, 117, 2959. https://doi.org/10.1002/ange.200500119
  17. Fillaut, J.-L.; Linares, J.; Astruc, J. Angew. Chem. Int. Ed. 1994, 33, 2460.
  18. Lambert, C.; Noll, G. Angew. Chem. Int. Ed. 1998, 37, 2107. https://doi.org/10.1002/(SICI)1521-3773(19980817)37:15<2107::AID-ANIE2107>3.0.CO;2-H
  19. Blackstock, S. C.; Selby, T. D. J. Am. Chem. Soc. 1998, 120, 12155. https://doi.org/10.1021/ja9821091
  20. Bonvoisin, J.; Launay, J.-P.; Auweraer, M. V. D.; Schryver, F. C. D. J. Phys. Chem. 1994, 98, 5052. https://doi.org/10.1021/j100070a018
  21. Bauld, N. L.; Bellville, D. J. Tetrahedron Lett. 1982, 23, 825. https://doi.org/10.1016/S0040-4039(00)86959-2
  22. Heo, R. W.; Somoza, F. B.; Lee, T. R. J. Am. Chem. Soc. 1998, 120, 1621. https://doi.org/10.1021/ja972871n
  23. Manners, I. Angew. Chem. Int. Ed. 1996, 35, 1602 https://doi.org/10.1002/anie.199616021
  24. Jeremie, B.; Mongin, O.; Jutand, A.; Ledoux, I., Zyss, J.; Blanchard-Desce, M. Chem. Mater 2003, 15, 4139. https://doi.org/10.1021/cm030392j
  25. Rathore, R.; Kumar, A. S.; Lindeman, S. V.; Kochi, J. K. J. Org. Chem. 1998, 63, 5847. https://doi.org/10.1021/jo980407a
  26. Rathore, Rajendra; Kochi, Jay K. J. Org. Chem. 1995, 60, 4399. https://doi.org/10.1021/jo00119a017
  27. Rathore, Rajendra; Burns, Carrie L.; Deselnicu, Mihaela I. Org. Lett. 2001, 3, 2887
  28. Kochi, J. K.; Rathore, R.; Magueres, P. L. J. Org. Chem. 2000, 65, 6826. https://doi.org/10.1021/jo000570h
  29. Smith, K.; Elmorsy, S. S.; Pelter, A. Tetrahedron Lett. 1991, 32, 4175 https://doi.org/10.1016/S0040-4039(00)79896-0
  30. Plater, M. J.; Mckay, M.; Jackson, T. Perkin Trans. 1 2000, 2695.
  31. Li, J.; Liu, D.; Li, Y.; Lee, C.-S.; Kwong, H.-L.; Lee, S. Chem. Mater. 2005, 17, 1208. https://doi.org/10.1021/cm034731k
  32. Thakkar, K.; Geahlen, R. L.; Cushman, M. J. Med. Chem. 1993, 36, 2950. https://doi.org/10.1021/jm00072a015
  33. Peters, G. M. Jr.; Stuber, F. A.; Ulrich, H. J. Org. Chem. 1975, 40, 2243. https://doi.org/10.1021/jo00903a026
  34. Cho, B. R.; Chajara, K.; Oh, H. J.; Son, K. H.; Jeon, S. J. Org. Lett. 2002, 4, 1703. https://doi.org/10.1021/ol025739n
  35. Meier, H.; Holst, H. C. Adv. Synth. Catal. 2003, 345, 1005- 1011 https://doi.org/10.1002/adsc.200303030
  36. Diez-Barra, E.; Garcia-Martinez, J. C.; Merino, S.; del Rey, R.; Rodriguez-Lopez, J.; Sanchez-Verdu, P.; Tejeda, J. J. Org. Chem. 2001, 66, 8832.
  37. Kim, K. S.; Tarakeshwar, P.; Lee, J. Y. Chem. Rev. 2000, 100, 4145. https://doi.org/10.1021/cr990051i
  38. Tarakeshwar, P.; Choi, H. S.; Kim, K. S. J. Am. Chem. Soc. 2001, 123, 3323. https://doi.org/10.1021/ja0013531
  39. Lee, E. C.; Hong, B. H.; Lee, J. Y.; Kim, J. C.; Kim, D.; Kim, Y.; Tarakeshwar, P.; Kim, K. S. J. Am. Chem. Soc. 2005, 127, 4530. https://doi.org/10.1021/ja037454r
  40. Meier, H.; Lehmann, M. Angew. Chem., Int. Ed. 1998, 37, 643. https://doi.org/10.1002/(SICI)1521-3773(19980316)37:5<643::AID-ANIE643>3.0.CO;2-4