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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Photophysics of Xanthene Dyes at High Concentrations in Solid Environments: Charge Transfer Assisted Triplet Formation
Yair Litman,Hernán B. Rodríguez,Silvia E. Braslavsky,Silvia E. Braslavsky,Silvia E. Braslavsky,Enrique San Román,Enrique San Román +6 more
TL;DR: Results demonstrate that photoactive energy traps, capable of yielding dye triplet states, can be formed even in highly‐concentrated systems with random dye distributions.
Journal ArticleDOI
One-Pot Strategy for Symmetrical and Unsymmetrical BOIMPY Fluorophores.
TL;DR: In this article, the authors report the improved direct access to red-emitting BOIMPY fluorophores (λ ≈ 600 nm) via a simple one-pot approach.
Journal ArticleDOI
3,5-Anthryl-Bodipy dyad/triad: Preparation, effect of F-B-F induced conformation restriction on the photophysical properties, and application in triplet-triplet-annihilation upconversion.
TL;DR: It is proposed that in dyads/triads, the charge separation and recombination-induced ISC outcompete the non-radiative decay to the ground state, which is new in the study of SOCT-ISC.
Journal ArticleDOI
Methyl Viologens of Bis‐(4’‐Pyridylethynyl)Arenes – Structures, Photophysical and Electrochemical Studies, and their Potential Application in Biology
Goutam Kumar Kole,Marta Košćak,Anissa Amar,Dragomira Majhen,Ksenija Bozinovic,Zlatko Brkljača,Matthias Ferger,Evripidis Michail,Sabine Lorenzen,Alexandra Friedrich,Ivo Krummenacher,Michael Moos,Holger Braunschweig,Abdou Boucekkine,Christoph Lambert,Jean-François Halet,Ivo Piantanida,Klaus Müller-Buschbaum,Todd B. Marder +18 more
TL;DR: In this article , a series of bis(4'−pyridylethynyl)arenes (arene=benzene, tetrafluorobenzene, and anthracene) were synthesized and their bis−N−methylpyrinium compounds were investigated as a class of π−extended methyl viologens.
Journal ArticleDOI
Effect of molecular conformation on the efficiency of the spin orbital charge recombination-induced intersystem crossing in bianthryls
Xiaoyu Zhao,Xiaoyu Zhao,A. A. Sukhanov,Kepeng Chen,Xinyu Geng,Xinyu Geng,Yu Dong,Violeta K. Voronkova,Jianzhang Zhao,Jianzhang Zhao,Lang Liu +10 more
TL;DR: In this paper, two bianthryl dyads, with two units connected at either the 2- or 9- positions of the anthryl moiety, were studied to establish the relationship between orientation and the electronic coupling and intersystem crossing (ISC) efficiency.
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.