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In a previous communication,2 we reported that 1,8-dilithionaphthalene reacts with elemental sulfur, selenium, and tellurium to yield naphtho[l,8-«/]-l,2-dithiole (I), naphtho[l,8-cí/]-l,2-diselenole (II) and naphtho[l,8-a/]-l,2-ditellurole (III), respectively. These compounds are good electron

The peri-bridged naphthalenes Cl0I+,XY with XY = SS, SSe, STe, SeSe, SeTe, TeTe all exhibit low first vertical ionization potentials at about 7.1 eV and, therefore, can be oxidized using AIC13/H2CC12. The radical cations generated (XY = SS to SeTe) are stable at room temperature. The chalcogen bridges dominate the species M'@ regarding spin population as well as charge distribution and, correspondingly, the ESR spectra reflect the effect of increasing spin/orbit inter- A novel and elegant synthesis6) reacting a THF solution of l,%dilithio-naphthalene at -78°C with powdered chalcogens has been extended successfully to prepare the mixed derivatives with SSe-, STe-, and SeTe-bridges7). Starting from known molecular properties of bis(methy1thio)-substituted naphthalenes3) as well as of Chem. Ber. 114(1981) 0 Verlag

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The peri-bridged naphthalenes Cl0I+,XY with XY = SS, SSe, STe, SeSe, SeTe, TeTe all exhibit low first vertical ionization potentials at about 7.1 eV and, therefore, can be oxidized using AIC13/H2CC12. The radical cations generated (XY = SS to SeTe) are stable at room temperature. The chalcogen bridges dominate the species M'@ regarding spin population as well as charge distribution and, correspondingly, the ESR spectra reflect the effect of increasing spin/orbit interaction S < Se < Te: line widths grow and g values raise linearly from 2.0086 (XU = SS) to 2.0409 (XU = SeTe). The PES ionization energies and the ESR coupling constants of sulfur-bridged derivatives are satisfactorily reproduced by a molecular state parametrized HMO model. Radikalionen, 46l-') Die Einelektronen-Oxidation 1.8-Chalkogen-iiberbriickter Naphthaline Die peri-iiberbriickten Naphthaline C,oH,XY mit XY = SS, SSe, STe, SeSe, SeTe, TeTe weisen alle niedrige erste vertikale Ionisierungspotentiale von etwa 7.1 eV auf und lassen sich daher mit AIC13/H2CC12 oxidieren. Die erzeugten Radikalkationen (XY = SS bis SeTe) sind bei Raumtemperatur stabil. Die Chalcogen-Briicken pragen die Species M'@ sowohl beziiglich der Spinpopulation wie der Ladungsverteilung und dementsprechend spiegeln die ESR-Spektren den Effekt zunehmender SpinIBahn-Wechselwirkung S < Se < Te wider: Die Linienbreiten wachsen und die 9-Faktoren erhohen sich linear von 2.0086 (XU = SS) bis auf 2.0409 (XY = SeTe). Die PES-Ionisierungsenergien und die ESR-Kopplungskonstanten der Schwefel-Derivate werden von einem HMO-Model1 mit Molekiilzustands-Parametern zufriedenstellend wiedergegeben. Peri-substituted naphthalenes containing dichalcogen bridges have received renewed interest as potential electron donors in one-dimensional organic charge-transfer cond u c t o r~~-~) .A novel and elegant synthesis6) reacting a THF solution of l,%dilithionaphthalene at -78°C with powdered chalcogens has been extended successfully to prepare the mixed derivatives with SSe-, STe-, and SeTe-bridges7). Starting from known molecular properties of bis(methy1thio)-substituted naphthalenes3) as well as of Chem. Ber. 114(1981) 0 Verlag