It is well known that diarylethenes undergo photocyclization, forming highly unstable 4a,4b-dihydrophenanthrenes (4a,4b-DHP) and derivatives which can readily undergo oxidative dehydrogenation, producing phenanthrenes and derivatives. During our recent investigation on photoreactivity of BMes2 and NMe2 functionalized diarylethenes, we discovered that stable 4a,4b-dihydrophenanthrenes and derivatives can be obtained and isolated quantitatively. Furthermore, we observed that the 4a,4b-DHP can undergo a facile thermal [1,5] H shift, forming 4a, 10a-DPH isomers. Control experiments established that p-substitution by a boron and an amino group on a phenyl ring plays a key in stabilizing DPHs. Oxidative dehydrogenation of DPHs led to the isolation of highly emissive BMes2 and NMe2 decorated phenanthrenes and derivatives. The details and the mechanistic insight on the photoreaction of donor-acceptor functionalized diarylethenes will be presented.

Donor-acceptor facilitated diarylethene photoisomerization

256th National Meeting (2018)

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