0000000000297240
AUTHOR
Walter Huber
Electron Transfer and Conformational Interconversions in 1, n ‐Diphenylpolyenes
1,4-Diphenylbutadiene (1), 1,6-diphenylhexatriene (2), and 1,8-diphenylocatatetraene (3) are reduced with alkali metals and the resulting paramagnetic monoanions and diamagnetic dianions characterized by ESR and (1H-, 13C-)NMR spectroscopy, respectively. The stereodynamic behavior of the ions is studied as a function of chain length, charge, and counterion. The reduction of 1, 2, and 3 serves as a model experiment for the doping of extended linear polyenes (polyacetylenes). Elektronenubertragungen und Konformationsanderungen in 1,n-Diphenylpolyenen 1,4-Diphenylbutadien (1), 1,6-Diphenylhexatrien (2) und 1,8-Diphenyloctatetraen (3) werden mit Alkalimetallen reduziert, und die resultierenden …
1,2,3,4,5‐[1′,8′] Anthra‐8,9;10,11‐dibenzo[13]annulene and 1,8‐Distyrylanthracene as Models for Phenylenevinylene Species. Syntheses, Structures, and Redox Properties
The synthesis of the title compound 4, formally a [13] perimeter, and of its acyclic model system, 1,8-distyrylanthracene (6) is described. The crystal structure of 4 reveals the configuration of the double bonds and the conformation of the macrocycle. Related findings come from the 1H-NMR spectroscopic characterization of 4 and 6 in solution. The spin density distribution of the radical anions 4−· and 6−· is interpretet in terms of the singly occupied molecular orbital and of the prevailing geometry. In contrast to 4, compund 6 proves to be an efficient electron acceptor since it can even be reduced to a tetraanion salt. The complete redox sequence is characterized by NMR and ESR spectrosc…