Abstract
Tetrathiafulvalenes. XXVII. Syntheses and Properties of cis- and trans-Isomers of Dihydrophenanthreno-Tetrathiafulvalenes The synthesis of anellated tetrathiafulvalenes (TTF) 10a–c, 11a–b via the 1,3-dithiolium salt/triethylamin or 1,3-dithiole-2-thione/triethyl phosphite route is described. The dihydrophenanthreno-anellated TTFs 10a, b can be thermally transformed into the phenanthreno-anellated TTFs 11a, b. Only in the case of the dihydrophenanthreno-anellated TTF 10b (with “α-naphthyl structure”) the isolation of the cis- and trans-isomer was possible due to differences in the solubility. Starting from the pure cis- or trans-isomer the radical salts of 10b are reducible to a 1:1 mixture of the cis/trans stereo isomers. The spectroscopic, electrochemical, and conductivity properties of the synthesized TTFs and their complexes with iodine, TCNQ, and DDQ are described.
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