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Synthesis and Spectral Properties of gem ‐Dimethyl Chlorin Photosensitizers
Author(s) -
Melissari Zoi,
Sample Harry C.,
Twamley Brendan,
Williams René M.,
Senge Mathias O.
Publication year - 2020
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.202000051
Subject(s) - singlet oxygen , chlorin , photodynamic therapy , geminal , chemistry , photosensitizer , density functional theory , photochemistry , derivatization , combinatorial chemistry , computational chemistry , oxygen , stereochemistry , organic chemistry , high performance liquid chromatography
Chlorins that bear a gem ‐dimethyl group, which facilitates their resistance to oxidation, are of interest for applications in photomedicine. Herein, we present the synthesis and the photophysical properties of two geminal ‐dimethyl chlorins (dihydroporphyrins) and their free base counterparts that act as efficient singlet oxygen generators and thus exhibit potential for use in photodynamic therapy (PDT) as anticancer or antimicrobial agents upon further derivatization. A complete characterization of their spectral and photophysical properties ( Φ f , Φ isc , Φ ic , Φ Δ , τ S , τ T , k f , k ic , k isc , k q ) is accompanied by density functional calculations (DFT) as well as time dependent (TD) DFT to investigate the features of the frontier molecular orbitals.