Bispyrene based chiroptical molecular redox switch

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Christian Westermeier, Hans-Christoph Gallmeier, Markus Komma and Jörg Daub


Abstract

The chiral trans-cyclohexanediol bispyrene esters (1R,2R)-1a and (1S,2S)-1b are reversibly reduced to the corresponding bisradical anions 1a2– and 1b2– which show strong absorption bands at 510 nm exhibiting exciton-split circular dichroism (CD) with opposite signs, whereas the radical anions of the bisamides 2a and 2b failed to show split CD signals.


References

  1. J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995 Search PubMed; Molecular Electronics, ed. J. Jortner and M. Ratner, Blackwell, Oxford, 1997 Search PubMed; A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher and T. E. Rice, Chem. Rev., 1997, 97, 1515 Search PubMed.
  2. T. Jin, K. Ichikawa and T. Koyama, J. Chem. Soc., Chem. Commun., 1992, 499 RSC; T. Saika, T. Iyoda, K. Honda and T. Shimidzu, J. Chem. Soc., Chem. Commun., 1992, 591 RSC; A. Knorr and J. Daub, Angew. Chem., Int. Ed. Engl., 1995, 34, 2664 CAS.
  3. B. L. Feringa, N. P. M. Huck and A. M. Schoevaars, Adv. Mater., 1996, 8, 681 CAS.
  4. J. Daub, I. Aurbach and J. Salbeck, Angew. Chem., Int. Ed. Engl., 1988, 27, 291 CrossRef; Angew. Chem., 1988, 100, 278 Search PubMed; J. Salbeck, I. Aurbach and J. Daub, Dechema Monographien, 1989, 112, 117 Search PubMed; M. Porsch, G. Sigl-Seifert and J. Daub, Adv. Mater., 1997, 9, 635 Search PubMed For a recent application of CD spectroelectrochemistry, see: Y. J. Lu, Y. C. Zhu, G. J. Cheng and S. J. Dong, Electroanalysis, 1999, 11, 601 CAS.
  5. The spectroelectrochemical cell has been described: J. Salbeck, Anal. Chem., 1993, 65, 2169 Search PubMed CD spectra were recorded on a JASCO J-710 spectropolarimeter.
  6. (a) N. Harada and K. Nakanishi, Circular Dichroic Spectroscopy, University Science Books, Oxford University Press, 1983 Search PubMed; (b) K. Nakanishi and N. Berova, in Circular Dichroism, Principles and Applications, ed. K. Nakanishi, N. Berova and R. W. Woody, VCH, New York, 1994, ch. 13, pp. 361–398 Search PubMed; (c) T. Nehira, C. P. Parish, S. Jockusch, N. J. Turro, K. Nakanishi and N. Berova, J. Am. Chem. Soc., 1999, 121, 8681 CrossRef CAS.
  7. A. Knorr, PhD thesis, Universität Regensburg, 1995. Pyrene radical anion has a characteristic and strong absorption at 488 nm under the same experimental conditions.
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