Quinoline-annulated chlorins and chlorin-analogs

Abstract

The OsO4-mediated dihydroxylation of quinoline-annulated porphyrin generates a quinoline-annulated dihydroxychlorin in a regioselective fashion. Its dihydroxypyrroline moiety, located at the opposite of the annulated pyrrole, is susceptible to the same functional group interconversions we previously demonstrated for non-annulated dihydroxychlorins: oxidations to the corresponding dione, lactone, and dialkoxymorpholine derivatives. The quinoline-annulated chlorin and derivatives are all characterized by absorption spectra that are much broadened and between 130 and 220 nm red-shifted compared to their non-annulated analogs. Absorbance maxima in the NIR up to well above 800 nm were recorded. We attribute the bathochromic shift to their extended [Formula: see text]-systems and inferred non-planarity, highlighting that quinoline-annulation is a particularly effective and simple strategy to red-shift the absorption spectra of chlorins and chlorin analogs.