Biphenyl-type electron acceptors exhibiting dynamic redox properties: a novel electrochromic system with ‘write protect’ option

Abstract

A novel redox pair undergoing reversible C–C bond making/breaking has been constructed based on a bis(dicyanovinyl)biphenyl derivative and a dianion with the dihydrophenanthrene skeleton; further cyclization of the latter to an enaminonitrile endows the ‘write protect’ option to its electrochromic response.

References

1. (a) P. R. Ashton, R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, S. Menzer, L. Pérez-García, L. Prodi, J. F. Stoddart, M. Venturi, A. J. P. White and D. J. Williams, J. Am. Chem. Soc., 1995, 117, 11 171; (b) D. J. Cárdenas, A. Livoreil and J.-P. Sauvage, J. Am. Chem. Soc., 1996, 118, 11 980.
2. M. Horner and S. Hünig, J. Am. Chem. Soc., 1977, 99, 6122; W. Freund and S. Hünig, J. Org. Chem., 1987, 52, 2154; T. Suzuki, J. Nishida and T. Tsuji, Angew. Chem., Int. Ed. Engl., 1997, 36, 1329; T. Suzuki, M. Kondo, T. Nakamura, T. Fukushima and T. Miyashi, Chem. Commun., 1997, 2325.
3. B. L. Feringa, W. F. Jager and B. de Lange, Tetrahedron, 1993, 49, 8267.
4. W. Lehnert, Tetrahedron Lett., 1970, 4723.
5. G. Wittig and W. Herwig, Chem. Ber., 1954, 87, 1511.
6. E. Campaigne, D. Mais and E. M. Yokley, Synth. Commun., 1974, 4, 379.
7. N. Neugebauer, A. J. Kos and P. von R. Schleyer, J. Organomet. Chem., 1982, 228, 107.
8. J. P. Schaefer and J. J. Bloomfield, Org. React. (New York), 1967, 15, 1.