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CAS: 850534-66-6
MF: C19H9BN2F2Br
MW: 393.99996
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Jian Xu

Institute of Chemistry, Chinese Academy of Sciences
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ZhiGang Xie

Changchun Institute of Applied Chemistry, Chinese Academy of Sciences
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Yi Xiao

Dalian University of Technology
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Co-reporter: Xinfu Zhang, Chao Wang, Liji Jin, Zhuo Han, and Yi Xiao
pp: 12372
Publication Date(Web):July 21, 2014
DOI: 10.1021/am503849c
Plasma membranes can sense the stimulations and transmit the signals from extracellular environment and then make further responses through changes in locations, shapes or morphologies. Common fluorescent membrane markers are not well suited for long time tracking due to their shorter retention time inside plasma membranes and/or their lower photostability. To this end, we develop a new bipolar marker, Mem-SQAC, which can stably insert into plasma membranes of different cells and exhibits a long retention time over 30 min. Mem-SQAC also inherits excellent photostability from the BODIPY dye family. Large two-photon absorption cross sections and long wavelength fluorescence emissions further enhance the competitiveness of Mem-SQAC as a membrane marker. By using Mem-SQAC, significant morphological changes of plasma membranes have been monitored during heavy metal poisoning and drug induced apoptosis of MCF-7 cells; the change tendencies are so distinctly different from each other that they can be used as indicators to distinguish different cell injuries. Further on, the complete processes of endocytosis toward Staphylococcus aureus and Escherichia coli by RAW 264.7 cells have been dynamically tracked. It is discovered that plasma membranes take quite different actions in response to the two bacteria, information unavailable in previous research reports.Keywords: fluorescence imaging; long wavelength; plasma membrane; probe; two-photon

Jianzhang Zhao

University of Bath
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Co-reporter: Ling Huang;Xiaoneng Cui; Bruno Therrien; Jianzhang Zhao
pp: 17472-17482
Publication Date(Web):
DOI: 10.1002/chem.201302492

Abstract

C60–bodipy triads and tetrads based on the energy-funneling effect that show broadband absorption in the visible region have been prepared as novel triplet photosensitizers. The new photosensitizers contain two or three different light-harvesting antennae associated with different absorption wavelengths, resulting in a broad absorption band (450–650 nm). The panchromatic excitation energy harvested by the bodipy moieties is funneled into a spin converter (C60), thus ensuring intersystem crossing and population of the triplet state. Nanosecond time-resolved transient absorption and spin density analysis indicated that the T1 state is localized on either C60 or the antennae, depending on the T1 energy levels of the two entities. The antenna-localized T1 state shows a longer lifetime (τT=132.9 μs) than the C60-localized T1 state (ca. 27.4 μs). We found that the C60 triads and tetrads can be used as dual functional photocatalysts, that is, singlet oxygen (1O2) and superoxide radical anion (O2.) photosensitizers. In the photooxidation of naphthol to juglone, the 1O2 photosensitizing ability of the C60 triad is a factor of 8.9 greater than the conventional triplet photosensitizers tetraphenylporphyrin and methylene blue. The C60 dyads and triads were also used as photocatalysts for O2.-mediated aerobic oxidation of aromatic boronic acids to produce phenols. The reaction times were greatly reduced compared with when [Ru(bpy)3Cl2] was used as photocatalyst. Our study of triplet photosensitizers has shown that broadband absorption in the visible spectral region and long-lived triplet excited states can be useful for the design of new heavy-atom-free organic triplet photosensitizers and for the application of these triplet photosensitizers in photo-organocatalysis.

Yu Qin

Nanjing University
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Tell Tuttle

University of Strathclyde
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Peter J. Skabara

University of Strathclyde
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Xiao-Bing Zhang

Hunan University
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Xiao-Bing Zhang

Hunan University
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Dong Xue

Shaanxi Normal University
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