Premium
Near‐Infrared BODIPY‐Acridine Dyads Acting as Heavy‐Atom‐Free Dual‐Functioning Photosensitizers
Author(s) -
Deckers Jasper,
Cardeynaels Tom,
Penxten Huguette,
Ethirajan Anitha,
Ameloot Marcel,
Kruk Mikalai,
Champagne Benoît,
Maes Wouter
Publication year - 2020
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.202002549
Subject(s) - bodipy , acridine , photochemistry , atom (system on chip) , chemistry , dual (grammatical number) , infrared , fluorescence , physics , optics , computer science , organic chemistry , art , literature , embedded system
Boron dipyrromethene (BODIPY) dyes represent a particular class within the broad array of potential photosensitizers. Their highly fluorescent nature opens the door for theragnostic applications, combining imaging and therapy using a single, easily synthesized chromophore. However, near‐infrared absorption is strongly desired for photodynamic therapy to enhance tissue penetration. Furthermore, singlet oxygen should preferentially be generated without the incorporation of heavy atoms, as these often require additional synthetic efforts and/or afford dark cytotoxicity. Solutions for both problems are known, but have never been successfully combined in one simple BODIPY material. Here, we present a series of compact BODIPY‐acridine dyads, active in the phototherapeutic window and showing balanced brightness and phototoxic power. Although the donor–acceptor design was envisioned to introduce a charge transfer state to assist in intersystem crossing, quantum‐chemical calculations refute this. Further photophysical investigations suggest the presence of exciplex states and their involvement in singlet oxygen formation.