Development and Characterization of Amino Donor–Acceptor Stenhouse Adducts
Elias Picazo presents the development of amino donor–acceptor Stenhouse adducts.
Piancatelli and related rearrangement reactions date back to as early as 1850 when Stenhouse reported the formation of a highly colored compound upon amine addition to furfural. Although the mechanism of reactivity was not fully elucidated until much later, these rearrangement reactions have provided a facile means to construct a hydroxy-substituted triene or cyclopentenone adducts. The resulting scaffolds find application in the synthesis of prostanoic acids and other natural products, Stenhouse salt derivatives, and most recently donor-acceptor Stenhouse adduct (DASA) photoswitches. The group of Professor Elias Picazo at the University of Southern California (Los Angeles, USA) initially became interested in DASA photoswitches because of their attractive photophysical features that set them apart from other molecular photoswitches. Professor Picazo said that “DASAs undergo isomerization from a vividly colored triene to a colorless cyclopentenone upon absorbing low-energy light. This process offers a gentle method to reversibly control substantial changes in size, charge, and color.”
Read the full article Development and Characterization of Amino Donor–Acceptor Stenhouse Adducts
