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,3aand 1,2-diphenyl-3-(1,2-diphenyl-3-azoindole)indole/TCNQ,5bare reported. In the two complexes, the distances between donor and acceptor planes range between 3.4 and 3.5 Å; in3atetracyanoethylene faces the phenyl ring of the indole, while in5bthe 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,Dcalc=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
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