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Complexes of azobisindoles with π-organic acceptors

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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.

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Correspondence to Giorgio Tosi.

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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

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Key Words

  • Infrared spectra
  • Raman spectra
  • molecular associations
  • azo compounds