Abstract
Five 6′-nitrospiro[indole-benzopyrans] have been reduced electrochemically in ACN to the corresponding radical anions. Their reduction potentials were in the range -1.32 to -1.40 V versus SCE, that is in the range expected for substituted nitrobenzenes. The EPR spectra of the species resulting from chemical reduction of the same compounds were also recorded, and suggested that the structure of the observed radicals varies with the reduction media: thus, while the spectra in DMSO could be attributed to the radical anions structurally similar to the starting compounds, those observed in THF under UV irradiation were assigned to the anions of the open merocyanines. It appears that also the species observed by reduction in DMF ought to be assigned the open structure.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
B. Tinland, R. Guglielmetti, and O. Chalvet, Tetrahedron 29, 665 (1973).
P. Appriou, R. Guglielmetti, and F. Garnier, J. Photochem. 8, 145 (1978).
A.S. Dvomikov, Ya.N. Malkin, and V.A. Kuz’min, Izv. Akad. Nauk SSSR, Ser. Khim. 1520 (1983).
S. Schneider, A. Mindl, G. Elfinfer, and M. Melzig, Ber. Bunsenges. Phys. Chem. 91, 1222 (1987).
C. Lenoble and R.S. Becker, J. Phys. Chem. 62, (1986).
R.S. Becker, Photochem. Photobiol. 48, 369 (1988) and references therein.
A.V. El’tsov, Organic Photochromes, Consultants Bureau, New York, 1990.
R. Guglielmetti in H. Dürr and H. Bouas-Laurent (Eds.), Photochromism. Molecules and Systems, Elsevier Science Publishers, Amsterdam, 1990, Chp. 8, p. 314, and references therein.
C. Bohne, M.G. Fan, Z.-J. Li, J. Lusztyk, and J.C. Scaiano, J. Chem. Soc., Chem. Commun. 571 (1990).
C. Bohne, M.G. Fan, Z.-J. Li, Y.C. Liang, J. Lusztyk, and J.C. Scaiano, J. Photochem. Photobiol. A: Chem. 66 79 (1992).
N. Tamai and H. Masuhara, Chem. Phys. Letters 191, 189 (1992).
W. Kemula, T.M. Krygowski in A.J. Barda and H. Lund (Eds.), Encyclopedia of Electrochemistry of the Elements, Organic Section, Vol. 13, Marcel Dekker, New York, 1979, pp. 78–126.
A. Berndt in K.-H. Hellwege (Ed.), Landolt-Börnstein New Series, Vol. 9, Part d1”, Springer Verlag, Berlin 1988, and referencees therein; A. Berndt in O. Madelung (Ed.), Landolt-Börnstein New Series, Vol. 17, Part f, Springer Verlag, Berlin 1988, and referencees therein.
A. Alberti, M. Lucarini, and G.F. Pedulli, Res. Chem. Intermed. 14, 259 (1990).
S. Hashimoto, A. Shimojima, T. Yuzawa, H. Hiura, J. Abe, and H. Takahashi, J. Mol. Structure 242, 1 (1991).
G. Pèpe and D. Siri in J.C. Rivail (Ed.), GenMol. A fast program for molecular modelling, in Molecular Modelling of Structure and Properties, Elsevier, Amsterdam, 1990, pp. 93–101.
C.K. Mann in A.J. Bard (Ed.), Electroanalytical Chemistry, Marcel Dekker, New York, 1969, pp. 57–134.
R.C. Bertelson in G.H. Brown (Ed.), Photochromism, Wiley, New York, 1971, Chp. III.
Y. Berchadski and G. Gronchi, Système S’acquisition BYGG.AEL, Catalogue de l’Agence Nationale du Logiciel (France), November, 1991.
G.F. Pedulli, M. Tiecco, A. Alberti, and G. Martelli, J. Chem. Soc., lPerkin 2 1816 (1973).
W.B. Forbes and P.D. Sullivan, J. Chem. Phys. 48, 1411 (1968).
M. Branca, A. Gamba, M. Barzaghi, and M. Simonetta, J. Am. Chem. Soc. 104, 6506 (1982).
P.H. Rieger and G.K. Fraenkel, J. Phys. Chem. 39, 609 (1963).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Campredon, M., Guglielmetti, R., Samat, A. et al. Radical anions from some photochromic nitrocompounds. An electron paramagnetic resonance and electrochemical study. Res Chem Intermed 19, 307–318 (1993). https://doi.org/10.1163/156856793X00127
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1163/156856793X00127