Photochromic molecules have been pursued as candidate materials for optical data storage, photoresponsive metal-organic frameworks, targeted drug delivery, sensors, molecular switches, and artificial muscles. Photoswitching is almost always achieved using UV light to drive the photoreaction in one direction, with visible light affecting the reverse reaction; a thermal pathway to isomerization may also be possible. Diaryethenes (DAEs) are of interest as they are robust and lack a thermal isomerization component; these photochromes can alternate between a ring open and a ring closed form, with the ring closing process usually requiring high-energy UV light. Efforts are now aimed at pushing the absorption of DAEs into the red and near IR regions of the spectrum, allowing the photochromic reactions to occur using visible and near IR light, making them more applicable within a biological context. However, current examples rely on lengthy syntheses and do not allow for further functionalization. We here report an approach utilizing a donor-acceptor type motif employing quinone electron acceptors. The syntheses are relatively short while providing DAEs that are amenable to further modification including the installation of stronger electron acceptors. We will present a series of related quinone based DAE examples while also exploring the potential of these adaptable systems in advanced polymers and photoresponsive metal-organic frameworks.

Revisiting the potential for quinone-based diarylethene photochromes: A theoretical and experimental study on naphthoquinone diarylethenes for advanced organic materials

251st National Meeting (2016)

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