title: Indachlorins: nonplanar indanone-annulated chlorin analogues with panchromatic absorption spectra between 300 and 900 nm.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Connecticut, Unit 3060, Storrs, CT 06269-3060 (USA).
authors.forename: Lalith P
authors.initials: LP
authors.lastname: Samankumara
authors.affiliation: Department of Chemistry, University of Connecticut, Unit 3060, Storrs, CT 06269-3060 (USA).
authors.forename: Sarina J
authors.initials: SJ
authors.lastname: Dorazio
authors.affiliation: Department of Chemistry, University of Connecticut, Unit 3060, Storrs, CT 06269-3060 (USA).
authors.forename: Joshua
authors.initials: J
authors.lastname: Akhigbe
authors.affiliation: Department of Chemistry, University of Connecticut, Unit 3060, Storrs, CT 06269-3060 (USA).
authors.forename: Ruoshi
authors.initials: R
authors.lastname: Li
authors.affiliation: Department of Chemistry, Youngstown State University, Youngstown, OH 44555-3663 (USA).
authors.forename: Arunpatcha
authors.initials: A
authors.lastname: Nimthong-Roldán
authors.affiliation: Department of Chemistry, Youngstown State University, Youngstown, OH 44555-3663 (USA).
authors.forename: Matthias
authors.initials: M
authors.lastname: Zeller
authors.affiliation: Department of Chemistry, University of Connecticut, Unit 3060, Storrs, CT 06269-3060 (USA). c.bruckner@uconn.edu.
authors.forename: Christian
authors.initials: C
authors.lastname: Brückner
keywords: UV/Vis spectroscopy; X-ray diffaction; chromophores; macrocycles; porphyrinoids