Synthesis and electrochemical redox properties of arylated p - PowerPoint PPT Presentation

Synthesis and electrochemical redox properties of arylated p ‐ benzoquinones, naphthoquinones and alkylamidoalkyl p benzoquinones naphthoquinones and alkylamidoalkyl ‐ p ‐ benzoquinones Mariam al Azani, Mazen al Sulaibi, Thies Thiemann, Miguel Ángel Montiel, Carlos Sánche Sánchez and Jesus Iniesta Sánche Sánchez and Jesus Iniesta Corresponding authors: thiesthiemann@yahoo.de and jesus.iniesta@ua.es

H 3 C O O CH 3 O 20 20 CH 3 H 3 C 10 H 3 C O O CH 3 O I (nA) 0 -10 -20 -1.8 -1.6 -1.4 -1.2 -1.0 -0.8 -0.6 -0.4 -0.2 0.0 -1.8 -1.6 -1.4 -1.2 -1.0 -0.8 -0.6 -0.4 -0.2 0.0 -1.8 -1.6 -1.4 -1.2 -1.0 -0.8 -0.6 -0.4 -0.2 0.0 + /Fc + /Fc + /Fc E vs Fc E vs Fc /Fc E vs Fc /Fc E vs Fc E vs Fc /Fc E vs Fc O O O 10 O + N Cl - O 5 O O O 0 I (nA) -5 -10 -15 -1.8 -1.6 -1.4 -1.2 -1.0 -0.8 -0.6 -0.4 -0.2 0.0 -1.8 -1.6 -1.4 -1.2 -1.0 -0.8 -0.6 -0.4 -0.2 0.0 -1.8 -1.6 -1.4 -1.2 -1.0 -0.8 -0.6 -0.4 -0.2 0.0 + /Fc + /Fc + /Fc E vs Fc E vs Fc E vs Fc Figure 1 . Cyclic voltammetry of 5 mM of benzoquinone (A), phenylbenzoquinone (B), 3 ‐ chlorophenylbenzoquinone (C), 3 ‐ nitrophenylbenzoquinone (D), 2,5 ‐ tert ‐ Butyl ‐ p ‐ benzoquinone (E) and phenylnaphthoquinone (F) in the ionic liquid [bmim][BF 4 ] 100 benzoquinone (E) and phenylnaphthoquinone (F) in the ionic liquid [bmim][BF 4 ]. 100 µm diameter Au microelectrode. Neat [bmim][BF 4 ] (red dashed line). Scan rate 100 mV/s. Third scan recorded.

O O O O O O O N NH 4 O O 2 0 I (nA) -2 -4 -6 -8 -1 .8 -1 .6 -1 .4 -1 .2 -1 .0 -0 .8 -0 .6 -0 .4 -0 .2 0 .0 -1 .8 -1 .6 -1 .4 -1 .2 -1 .0 -0 .8 -0 .6 -0 .4 -0 .2 0 .0 + /F + /F E v s F c c E v s F c c Figure 2 . Cyclic voltammetry of 5 mM of N ‐ Benzyl 3 ‐ (1,4 ‐ dimethoxyphen ‐ 2 ‐ yl)propionamide ( 16a ) (A), and N ‐ Benzyl carboxamidoethyl ‐ p ‐ benzoquinone ( 16b ) (B) in the ionic liquid [bmim][BF 4 ]. 100 µm diameter Au microelectrode. Scan rate 100 mV/s. Third scan recorded.