Generation of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitro
Mikhail A. Filatov,Safakath Karuthedath,Pavel M. Polestshuk,Huguette Savoie,Keith J. Flanagan,Cindy Sy,Elisabeth Sitte,Maxime Telitchko,Frédéric Laquai,Ross W. Boyle,Mathias O. Senge +10 more
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TLDR
1O2 generation by BADs in living cells enables visualization of the dyads distribution, promising new imaging applications.Abstract:
Heavy atom-free BODIPY-anthracene dyads (BADs) generate locally excited triplet states by way of photoinduced electron transfer (PeT), followed by recombination of the resulting charge-separated states (CSS). Subsequent quenching of the triplet states by molecular oxygen produces singlet oxygen (1O2), which reacts with the anthracene moiety yielding highly fluorescent species. The steric demand of the alkyl substituents in the BODIPY subunit defines the site of 1O2 addition. Novel bis- and tetraepoxides and bicyclic acetal products, arising from rearrangements of anthracene endoperoxides were isolated and characterized. 1O2 generation by BADs in living cells enables visualization of the dyads distribution, promising new imaging applications.read more
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Strategic Construction of Sulfur-Bridged BODIPY Dimers and Oligomers as Heavy-Atom-Free Photosensitizers.
TL;DR: In this paper, an efficient strategy for building sulfur-bridged oligo-BODIPYs based on the SNAr reaction is described, which showed broadband and strong visible-near-infrared (NIR) light absorption, strong intramolecular exciton coupling, and efficient intersystem crossing.
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Zinc-based Metal Organic Framework Derived From Anthracene and BODIPY Chromophores: Synthesis and Photophysical Properties
Journal ArticleDOI
Red/NIR Thermally Activated Delayed Fluorescence from Aza-BODIPYs
Edurne Avellanal-Zaballa,Alejandro Prieto-Castañeda,Fernando García-Garrido,Antonia R. Agarrabeitia,Esther Rebollar,Jorge Bañuelos,Inmaculada García-Moreno,Maria J. Ortiz +7 more
TL;DR: The computational-aided photophysical study under mild and hard irradiation regimes disclose the interplay between molecular structure and photonic performance to develop long-lived fluorescence red emitters through thermally activated reverse intersystem crossing.
Journal ArticleDOI
Charge Separation/Recombination, Intersystem Crossing, and Unusually Slow Intramolecular Triplet-Triplet Energy Transfer in Naphthalenediimide-Anthracene Compact Energy Donor-Acceptor Dyads.
Xi Chen,A. A. Sukhanov,Maria Taddei,Bernhard Dick,Jianzhang Zhao,Violeta K. Voronkova,Mariangela Di Donato +6 more
TL;DR: In this paper , three anthracene (An)-naphthalenediimide (NDI) compact electron donor-acceptor dyads were prepared, and the intersystem crossing mechanism is spin orbit charge transfer ISC (SOCT-ISC) for all the dyads; for 9-An-NDI, only the 3An state was observed, while for the other two dyads, both 3NDI and 3An states were observed, with their relative population changing with increasing delay time.
References
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Journal ArticleDOI
BODIPY dyes in photodynamic therapy.
TL;DR: The attributes of BODIPY dyes for PDT are summarized, and substituents with appropriate oxidation potentials are summarized in some related areas.
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Reaction-based small-molecule fluorescent probes for chemoselective bioimaging
TL;DR: A survey of tools and tactics for using small-molecule fluorescent probes to detect biologically important chemical analytes is presented, highlighting design criteria for effective chemical tools for use in biological applications as well as gaps for future exploration.
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The triplet excited state of Bodipy: formation, modulation and application
TL;DR: The methods for switching (or modulation) of the triplet excited state of Bodipy were discussed, such as those based on the photo-induced electron transfer (PET), by controlling the competing Förster-resonance-energy-transfer (FRET), or the intermolecular charge transfer (ICT).
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Design and Synthesis of a Library of BODIPY-Based Environmental Polarity Sensors Utilizing Photoinduced Electron-Transfer-Controlled Fluorescence ON/OFF Switching
TL;DR: A library of probes in which the threshold of fluorescence ON/OFF switching corresponds to different levels of solvent polarity is designed and synthesized, which were used to examine bovine serum albumin and living cells and concluded to be similar to that of acetone.