A series of symmetrical and unsymmetrical (indolyl)methanes were synthesized using the Ball milling methodology. The redox switching of the prepared compounds was studied by exploiting their multi-responsive behavior towards oxidants (light/oxygen), reductants (NaBH 4 , hydrogen with Pd/C or palladium-doped magnetic nanoparticles) and electrochemical modulation. Coumarin-derived (indolyl)methane exhibited distinct color variation and emission On/Off during the redox switching which could be useful in materials/biomaterials applications. Overall, this paper describes the design, synthesis and demonstration of the multi-responsive behavior of (indolyl)methanes towards redox switching.
A series of biscoumarin-fused 2,6,9trioxabicyclo[3.3.1]nona-3,7-dienes were synthesized from base-mediated coupling of 4-hydroxycoumarins with benzoyl cyanides and followed by treating with pyridine and thionyl chloride. The mechanism of this reaction was proposed to involve the formation of (E)-2-(2,4-dioxochroman-3-ylidene)-2-phenylacetonitrile as a key intermediate, which could further react with 2-(2,4-dioxochroman-3-yl)-2-hydroxy-2-phenylacetonitrile to yield biscoumarin-fused trioxabicycles.
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