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Indachlorins: Nonplanar Indanone‐Annulated Chlorin Analogues with Panchromatic Absorption Spectra between 300 and 900 nm
Author(s) -
Samankumara Lalith P.,
Dorazio Sarina J.,
Akhigbe Joshua,
Li Ruoshi,
NimthongRoldán Arunpatcha,
Zeller Matthias,
Brückner Christian
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501230
Subject(s) - bathochromic shift , chemistry , chlorin , pyrrole , chromophore , photochemistry , stereochemistry , absorption spectroscopy , ring (chemistry) , moiety , tetrapyrrole , crystallography , porphyrin , fluorescence , organic chemistry , physics , enzyme , quantum mechanics
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. The parent free base indaphyrin has been crystallographically characterized, highlighting its strongly ruffled conformation incorporating a helimeric twist. It 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.