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http://hdl.handle.net/1942/32818
Title: | Near‐Infrared BODIPY‐Acridine Dyads Acting as Heavy‐Atom‐Free Dual‐Functioning Photosensitizers | Authors: | DECKERS, Jasper CARDEYNAELS, Tom PENXTEN, Huguette ETHIRAJAN, Anitha AMELOOT, Marcel Kruk, Mikalai Champagne, Benoit MAES, Wouter |
Issue Date: | 2020 | Publisher: | WILEY-V C H VERLAG GMBH | Source: | CHEMISTRY-A EUROPEAN JOURNAL, 26 (66) , p. 15212 -15225 | Abstract: | 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. | Notes: | Maes, W (corresponding author), UHasselt Hasselt Univ, Inst Mat Res IMO, Design & Synth Organ Semicond DSOS, B-3590 Diepenbeek, Belgium.; Maes, W (corresponding author), IMEC, Associated Lab IMOMEC, Wetenschapspk 1, B-3590 Diepenbeek, Belgium. wouter.maes@uhasselt.be |
Other: | Maes, W (corresponding author), UHasselt Hasselt Univ, Inst Mat Res IMO, Design & Synth Organ Semicond DSOS, B-3590 Diepenbeek, Belgium ; IMEC, Associated Lab IMOMEC, Wetenschapspk 1, B-3590 Diepenbeek, Belgium. wouter.maes@uhasselt.be | Keywords: | BODIPY dyes;fluorescence;near-infrared;photosensitizers;singlet oxygen | Document URI: | http://hdl.handle.net/1942/32818 | ISSN: | 0947-6539 | e-ISSN: | 1521-3765 | DOI: | 10.1002/chem.202002549 | ISI #: | WOS:000579248300001 | Category: | A1 | Type: | Journal Contribution | Validations: | ecoom 2021 |
Appears in Collections: | Research publications |
Files in This Item:
File | Description | Size | Format | |
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chem.202002549.pdf Restricted Access | Published version | 2.9 MB | Adobe PDF | View/Open Request a copy |
Revised manuscript Deckers et al_CEJ 2020.pdf | Peer-reviewed author version | 1.93 MB | Adobe PDF | View/Open |
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