A New Type of π-Electron Donors with One Dithiole Unit: Substituted 7-(1,3-Dithiol-2-ylidene)-7-hydrobenz[d,e]anthracenes
✍ Scribed by Nazario Martín; Enrique Ortí; Luis Sánchez; Pedro M. Viruela; Rafael Viruela
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 359 KB
- Volume
- 1999
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
New electron donors 11a-c bearing only one 1,3-dithiole ring monocation exhibit butterfly-shaped non-planar structures, the dication is fully aromatic and consists of a closed-shell, conjugated with an acene backbone have been synthesized by Wittig-Horner reactions from 7H-benz [d,e]anthracen-7-singly charged, planar polyacenic unit and a singly charged dithiole ring. The third redox process can be assigned to a one (10) and differently substituted phosphonate esters 9ac. The donor properties of 11 have been characterized by second oxidation of the acene unit. The high aromaticity of the dication, coupled with the particular donor ability of the means of both experimental techniques and quantum chemical calculations. Cyclic voltammetry measurements on acene unit are shown to be the key factors in accounting for the electrochemical behaviour and the enhanced donor the novel compounds predict donor abilities comparable to those of TTF and BEDT-TTF. The voltammograms show a properties of the novel compounds. Theoretical calculations also help to rationalize the UV/Vis data in that they predict multi-stage redox behaviour with oxidation up to the trication, where the first two oxidation processes take place the appearance of a low-energy, intramolecular chargetransfer absorption band for the neutral compounds. Stable at very close potentials. These processes have been assigned to a simultaneous oxidation of the dithiole and acene charge-transfer complexes with a 2:3 (D/A) stoichiometry have been prepared by reaction with the strong acceptors moieties on the basis of DFT/B3-P86/6-31G* theoretical calculations. Whereas the neutral compound and the TCNQF 4 and DDQ.
termolecular S•••S contacts