Indachlorins: Chlorin Analogues with Panchromatic Absorption Spectra Between 300 and 900 nm

Indaphyrins, pyrrole-modified porphyrins containing a cleaved pyrrole β,β’-bond and two annulated indanone moieties, possess unusually broadened and redshifted UV/Vis spectra because of their π-expanded chromophores. Its free base has been crystallographically characterized, highlighting its strongly ruffled conformation incorporating a helimeric twist. Free base indaphyrin was shown to be susceptible to regiospecific derivatizations at the opposite side of the ring-cleaved pyrrole (dihydroxylation, followed by functional group transformations of the resulting diol functionality), generating indaphyrin-based chlorin analogues, indachlorins, that incorporate a dihydroxypyrroline, pyrrolindione, oxazolone, or a morpholine moiety. Structural modifications resulted in further broadening and hyper- and bathochromic shifts of the optical spectra, some of which possess a nearly panchromatic absorption between 300 to well above 900 nm. The extents to which these modifications affect their solid-state conformations were analyzed:

Samankumara, L.; Dorazio, S.; Akhigbe, J.; Li, R.; Nimthong-Roldán, A.; Zeller, M.; Brückner, C. ‘Indachlorins: Nonplanar Indanone-Annulated Chlorin Analogues with Panchromatic Absorption Spectra Between 300 and 900 nm’ Chem.–Eur. J. 2015, accepted for publication.