Synthesis and Photooxygenation of 2,3,6-Trimethylfuronaphthopyrida-5,7-dione, A Potential Chemiluminescent Probe for Singlet Oxygen

Article abstract of DOI:10.1016/S0040-4020(01)80310-0

As potential chemiluminescent probe for singlet oxygen, the furonaphthalimide 4 was synthesized in five steps (ca. 25percent overall yield), by starting from commercially available 4-chloro-1,8-naphthalic anhydride; its photooxygenation at -10 deg C gave the cleavage product 6 of the intermediary dioxetane 5, which is thermally too labile for isolation and could not be detected even by low temperature NMR spectroscopy.The new 1,8-naphthalimide derivatives 3,4 and 6 were fully characterized and their absorption and fluorescence spectral properties were determined.