Development and characterization of amino donor-acceptor Stenhouse adducts.

ABSTRACT: Donor-acceptor Stenhouse adducts (DASAs) are molecular photoswitches spurring wide interest because of their dynamic photophysical properties, complex photoswitching mechanism, and diverse applications. Despite breakthroughs in modularity for the donor, acceptor, and triene compartments, the backbone heteroatom remains static due to synthetic challenges. We provide a predictive tool and sought-after strategy to vary the heteroatom, introduce amino DASA photoswitches, and analyze backbone heteroatom effects on photophysical properties. Amino DASA synthesis is enabled by aza-Piancatelli rearrangements on pyrrole substrates, imparting an aromaticity-breaking rearrangement that capitalizes on nitrogen's additional bonding orbital and the inductive properties of sulfonyl groups. Amino DASA stru

SUBMITTER: Reyes CA 

PROVIDER: S-EPMC11217284 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature