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, Na2SO4 (99%) were purchased from Alfa Aesar and 2,2-diphenyl-1-picrylhydrazyl (DPPH) were purchased from SIGMA. Tetrabutylammonium hexafluorophosphate (Aldrich) and acetonitrile (HPLC grade, Carlo Erba) were used as received for electrochemical studies. Triethylamine (99.5%) from Aldrich, Tetrahydrofuran (THF, HPLC grade), diethyl ether (Analysis grade), ethyl acetate (Reagent grade), Dichloromethane (DCM, HPLC grade), cyclohexane (Reagent grade), petroleum ether (Reagent grade), dichloromethane (DCM, Reagent grade) from Carlo Erba and glacial acetic acid, Sodium azide (99%), tBuOK (98%), CuI (98%) and PPh3 (99%) was received from ACROS, PdCl2 (99.9%) was received from STREM, triisopropylsilylacetylene (97%) and, p.4
, Aldrich were used for NMR analysis. Glassy carbon (GC) electrodes from Bioanalytical Systems Inc. (model MF-2012; 3 mm in diameter) were used for cyclic voltammetry. GC sheets from Alfa Aesar were used for XPS and pyrolyzed photoresist film (PPF), 2SO (99.9%) and CDCl3 (99.8%) from
, ) was added drop wise at 0°C. After 15 min stirring, the precipitated was filtered and washed with diethyl ether to afford the diazonium salt in 90% yield as a beige solid. 1 H NMR (300 MHz, (CD3)2SO): ? (ppm) = 8.43 (d, 2H, J = 9
, 46 mL, 10.97 mmol, 1.10 equiv.) in a mixture of 4-iodoaniline (2.18 g, 9.97 mmol, 1 equiv, (triisopropylsilyl)ethynyl)aniline was obtained under argon atmosphere by dropwise addition of triisopropylsilylacetylene, p.20
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