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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Spiro rhodamine-coumarin compact electron donor–acceptor dyads: synthesis and spin–orbit charge transfer intersystem crossing
TL;DR: In this article , spiro rhodamine (RB)-coumarin (Cou) compact electron donor-acceptor dyads were used to study the charge transfer and spin-orbit CT intersystem crossing (SOCT-ISC).
Journal ArticleDOI
Ethyl 5-methyl-3-[11-(pyridin-2-yl)-6,11-di-hydro-6,11-ep-oxy-dibenzo[b,e]oxepin-6-yl]isoxazole-4-carboxylate: a bicyclic acetal from the rearrangement of an anthracenyl isoxazole.
TL;DR: The title compound, a rearrangement product of an o-pyridinyl anthracenyl isoxazole ester, features a bicyclic acetal structure, which has two extended almost co-planar ring systems, which subtend a fold angle of 102.17 (5)°.
Journal ArticleDOI
Delivering Singlet Oxygen in Dark Condition With an Anthracene-Functionalized Semiconducting Compound for Enhanced Phototheranostics
Jianmin Shen,Liu Pan,Xujing Zhang,Zhenyuan Zou,Bo Wei,Yongchang Chen,Xiaoyan Tang,Dengfeng Zou +7 more
TL;DR: The results provide a strategy to design a heavy-atom–free photosensitizer for photothermal and fractionated PDT against kidney tumors and H&E analysis of the normal tissues indicates that such NPs cause no side effects, indicating the biosafety of DPPA NPs.
Journal ArticleDOI
Ultrafast Charge Separation Driven by Torsional Motion in Orthogonal Boron Dipyrromethene Dimer.
TL;DR: In this article , the photoinduced charge separation via symmetry breaking in an orthogonal meso-β-linked boron dipyrromethene (BODIPY) dimer was investigated by polarized transient absorption spectroscopy.
Journal ArticleDOI
Origin of intersystem crossing in highly distorted organic molecules: a case study with red light-absorbing N,N,O,O-boron-chelated Bodipys
Xue Zhang,Andrey Sukhanov,Xi Jing Liu,Maria Taddei,Jianzhang Zhao,Anthony Harriman,Violeta K. Voronkova,Yan Wan,Bernhard Dick,Mariangela Di Donato +9 more
TL;DR: In this paper , the authors explored the relationship between twisted π-conjugation framework of aromatic chromophores and the efficacy of intersystem crossing (ISC) and found that the twisted framework does not necessarily induce ISC, but S1/Tn energy matching may be a generic feature for increasing ISC for a new generation of heavy atom-free triplet photosensitizers.
References
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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.