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The redox behaviour of aza-substituted naphtho- and anthraquinones, which offer O=C–C=N– chelate tongs for an advantageous five-membered ring metal cation complexation, is investigated by a combination of cyclovoltammetric and ESR/ENDOR spectroscopic measurements. The formation of paramagnetic contact ion pairs like [(quinoline-5,8-semiquinone)· ⊖ Me ⨁ ]·, with Me ⨁  = Li ⨁ , Na ⨁ , Tl ⨁ , or of triple ion radical cations like [(1,4-diazo-9,10-anthrasemiquinone) e Me ⨁ ]· ⨁ , with Me ⨁  = Li⨁, Na ⨁  is corroborated both by shifts of the second reduction potential of up to 0,67 V for e.g. quinoline 5,8-quinone upon addition of Li ⨁ [B(C 6 H 5 ) 4 ] ⊖  to its DMF solution and by the observation of ESR/ENDOR metal couplings.

zeitschrift für naturforschung b

Elektronentransfer und Ionenpaar-Bildung, 18 [1 -3] / Electron Transfer and Ion Pairing, 18 [ 1 - 3]: Radikalanionen und Radikal-Ionenpaare aza-substituierter Naphtho- und Anthrachinone / Radical Anions and Radical Ion Pairs of Aza-Substituted N aphtho- and Anthraquinones