The aerobic oxidation of alcohols to their corresponding carbonyl compounds could be efficiently accomplished by using the combination of cobalt nitrate, dimethylglyoxime and 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) as a novel catalytic system, and various alcohols including primary and secondary benzylic, allylic and aliphatic alcohols could be quantitatively converted to the corresponding aldehydes or ketones at 70 8C under 0.4 MPa dioxygen pressure in dichloromethane. During the oxidation, the in situ generated cobaloxime and nitric oxide (NO) were responsible for the activation of dioxygen, respectively, thereby, two concerted catalytic routes exist: cobaloxime-activating-dioxygen TEMPO-catalyzed and NO-activating-dioxygen TEMPO-catalyzed aerobic oxidation of alcohols.
(R,R)-Salen-based chiral polymer P-1 was synthesized by the polymerization of 5,5'-((2,5-dibutoxy-1,4-phenylene)bis(ethyne-2,1-diyl))bis(2-hydroxy-3-(piperidin-1-ylmethyl) benzaldehyde (M-1) with (1R,2R)-cyclohexane-1,2-diamine (M-2) via nucleophilic addition- elimination reaction, and (R,R)-salan-based polymer P-2 could be obtained by the reduction reaction of P-1 with NaBH(4). (R,R)-Salen-based chiral polymer P-1 can exhibit greater fluorescence enhancement response toward (l)-α-hydroxyl carboxylic acids, and the value of enantiomeric fluorescence difference ratio (ef) can reach as high as 8.41 for mandelic acid and 6.55 for lactic acid. On the contrary, (R,R)-salan-based chiral polymer P-2 shows obvious fluorescence quenching response toward α-hydroxyl carboxylic acids. Most importantly, (R,R)-salen-based polymer P-1 can display bright blue fluorescence color change in the presence of (l)-α-hydroxyl carboxylic acids under a commercially available UV lamp, which can be clearly observed by the naked eyes.
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