Abstract
Complexes of azobisindoles with tetracyanoethylene and tetracyanoquinodimethane were studied by UV-Vis, FT-IR, Raman, NMR and X-ray spectroscopies. FT-IR and Raman spectra, as well as X-ray analysis, gave useful information on the participation of various sites to the association, through analysis of CN and N=N vibrational modes, while UV-Vis and NMR spectra were less helpful. The crystal structure of complexes 1-ethyl-2-phenyl-3-(1-ethyl-2-phenyl-3-azoindole)indole/TCNE,3a and 1,2-diphenyl-3-(1,2-diphenyl-3-azoindole)indole/TCNQ,5b are reported. In the two complexes, the distances between donor and acceptor planes range between 3.4 and 3.5 Å; in3a tetracyanoethylene faces the phenyl ring of the indole, while in5b the superposition of tetracyanoquinodimethane with the donor is negligible. Compound3a,P−1,a=9.504(2),b=9.513(3),c=8.941(2) Å, α=97.81(4), β=103.38(3), γ=84.14(2)°,Z=2,D calc=2.55 g cm−3; compound5b,P−1,a=12.648(3),b=12.205(2),c=7.263(3) Å, α=103.69(2), β=91.23(3), γ=110.61(2)°,Z=2,D calc=2.53 g cm−3.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Fatiadi, A. J.The Chemistry of Functional Groups, Supplement C; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1983; chapter 26.
Foster, R.,Molecular Complexes, Vol. 2; Foster, R., Ed.; Elek Science: London, 1974.
Fukuzumi, S.; Kochi, J. K.:Tetrahedron,1981,38, 1035.
Fukuzumi, S.; Mochida, K.; Kochi, J. K.:J. Am. Chem. Soc. 1979,101, 5961.
Bruni, P.; Cardellini, L.; Conti, C.; Giorgini, E.; Tosi, G.Monatsh. Chem. 1992,121, 165.
Bocelli, G.; Cardellini, L.; De Meo G.; Ricci, A.; Rizzoli, C.; Tosi, G.;J. Crystallogr. Spectr. Res. 1990,20, 561.
Chudek, J. A.; Foster, R.; Mackay, R. L.; Page, F. M.; Twiselton, D. R.J. Chem. Soc., Faraday Trans. 1,1988,84, 1145.
Cipiciani, A.; Santini, S.; Savelli, G.:J. Chem. Soc., Faraday Trans. I 1979, 497.
Sung, M. T.; Parker, J. A.;Proc. Natl. Acad. Sci. USA 1972,69, 1196.
Blackstock, S. C.; Kochi, J. K.J. Am. Chem. Soc. 1987,109, 1987.
Giorgini, E.; Tosi, G.; Bocelli, G.,J. Cryst. Spectr. Res. 1992,22, 443.
Colonna, M.; Greci, L.; Bruni, P.;Gazz. Chim. Ital. 1972,102, 527.
Belletti, D.; Cantoni, A.; Pasquinelli, G.Gestione on-line di diffrattometro a cristallo singolo Siemens AED con sistema PC IBM compatibile. Centro di studio per la strutturistica diffrattometrica del C.N.R.: Parma. Internal report 1/93, 1993.
Sandrolini, F.Macromolecole: Scienza e Tecnologia, Vol. 2; Pacini: Pisa 1986.
Hindawey, A. M.; Nassar, A. M. G.; Issa, R. M.;Acta Acad. Sci. Hungaricae,1977,92, 263.
Issa, R. M.; El-Essawey, M. M.J. Phys. Chem. (Leipzig) 1973,253, 96.
Knoss, R. D.; Fassel, V. A.;J. Am. Chem. Soc. 1960,79, 316.
Bruni, P.; Giorgini, E.; Marrosu, G.; Maurelli, E.; Tosi, G.Gazz. Chim. Ital. 1992,122, 175.
Sasaki, A.; Aihara, J.; Matsunaga, Y..Bull. Chem. Soc. Jpn. 1974,47, 2926.
Kuder, J. E.; Limburg, W. W.; Pochan, J. M.; Wychick, D.J. Chem. Soc. Perkin Trans. II 1977, 1643.
Meier, H.Organic Semiconductors 2; Ebel, H. F., Ed.; Verlag Chemie: Weinheim, 1974.
Bruni, P.; Cardillo, B.; Giorgini, E.; Tosi, G.; Bocelli, G.; Cantoni, A.Spectrochim. Acta 1990,3, 389, and papers quoted therein.
Poradowska, H.; Czuba, W.; Lorenz, K.; Chyla, A..J. Roy. Neth. Chem. Soc..1977,96, 42.
Hamilton, W. C.,Acta Crystallogr. 1959,12, 609.
Kistenmacher, T. J.; Emge, T. J.; Bloch, A. N.; Cowan, D. O.Acta Crystallogr. 1982,B38, 1193.
Tosi, G.; Cardellini, L.; Bocelli, G.Acta Crystallogr. 1988,B44, 55.
Sheldrick, G. M.:Crystallographic Computing 3. Sheldrick, G. M.; Kruger, G.; Goddard, R. Eds.; Oxford University Press, 1985; pp. 175–189.
Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Polidori, G.J. Appl. Crystallogr. 1994, submitted for publication.
Sheldrick, G. M.,SHELX76, Programs for the solution of crystal structure determinations. Univ. of Cambridge: England, 1976.
Nardelli, M.:Comput. Chem. 1983,7, 95.
Johnson, C. K.;ORTEP Report ORNL-5138, Oak Ridge National Laboratory: Tenn., 1976.
Motherwell, W. D. S., and Clegg, W..PLUTO A program for plotting molecular and crystal structures. University of Cambridge: England, 1978.
Rizzoli, C.; Sangermano, V.; Calestani, G.; Andreetti, G. D. CRYSRULER.J. Appl. Crystallogr. 1987,20, 436.
Ibers, J. A.; Hamilton, W. L., Eds.International Tables for X-Ray Crystallography, Vol. IV; Kynoch Press: Birmingham, U.K. 1974; pp 152–172.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Bruni, P., Bocelli, G., Cantoni, A. et al. Complexes of azobisindoles with π-organic acceptors. J Chem Crystallogr 25, 683–691 (1995). https://doi.org/10.1007/BF01665976
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01665976