66183-99-1Relevant articles and documents
Electron Donor-Acceptor Compounds, XXIX. Electron Donor-Acceptor Paracyclophanes with 7,7,8,8-Tetracyanoquinodimethane (TCNQ) as Acceptor Unit
Staab, Heinz A.,Knaus, Guenter H.,Henke, Hans-Eckard,Krieger, Claus
, p. 2785 - 2807 (2007/10/02)
Electron donor-acceptor paracyclophanes 1, 2, 13, and 14 which contain 7,7,8,8-tetracyanoquinodimethane (TCNQ) as acceptor component have been synthesized.Key intermediates for the syntheses of 1 and 2 were the paracyclophanes 5 and 6, resp., which were prepared via the corresponding dithiaparacyclophanes. 5 was transformed via 7, 9, and 11 into the TCNQ phane 1, analogously 6 via 8, 10, and 12 into the isomeric 2.X-ray structure analyses of 1 and 2 confirm the assignment to the pseudoortho and pseudogeminal series; molecular and crystal structures of 1 and 2 are discu ssed. 1 and 2 show charge transfer absorptions at long wavelength which differ considerably in their intensity and wavelength as a consequence of different donor-acceptor orientations. - The syntheses of the paracyclophane systems 13 and 14 started from dithiaparacyclophanes 17/18 which by pyrolysis of their disulfones 19/20 yielded the paracyclophanes 15 and 16.The assignment to the pseudoortho and pseudogeminal series was established by X-ray structure analysis of 16.Conversion of 15 and 16 into 13 and 14, resp., was performed in analogy to the syntheses of 1 and 2 (15 -> 21 -> 23 -> 25 -> 13 and 16 -> 22 -> 24 -> 26 -> 14).Electron donor-acceptor interactions in 13 and 14 were investigated.In comparison to 1/2 much more pronounced intensity differences of the charge transfer absorptions are observed for the pair of isomers 13 and 14. - Synthesis and properties of TCNQ-paracyclophane 28 are reported.
