Journal ArticleDOI
A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes.
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TLDR
This work clearly demonstrates that the fluorinated, highly stabilised carbanionic substituent is a new option for controlling the macroscopic property of chemical materials.Abstract:
Installation of a carbanionic substituent, that is strongly stabilised by two (trifluoromethyl)sulfonyl (Tf = SO 2 CF 3 ) groups, into several fluorescence dyes including boron-dipyrromethenes (BODIPYs), fluoresceins, and aminocoumarins has been achieved by the 2,2-bis(triflyl)ethylation reaction of the dye frameworks with highly electrophilic Tf 2 C=CH 2 , followed by neutralisation with NaHCO 3 . Despite the contradiction between water-solubility and lipophilicity, the carbanion-decorated dyes thus obtained showed significant enhancement of not only water-solubility but also lipophilicity. This work clearly demonstrates that the fluorinated, highly stabilised carbanionic substituent is a new option for controlling the macroscopic property of chemical materials.read more
Citations
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BODIPY as a Multifunctional Theranostic Reagent in Biomedicine: Self‐Assembly, Properties, and Applications
Hong Cheng,Xiaoqiao Cao,Shuchun Zhang,Keyue Zhang,Yang Cheng,Jiaqi Wang,Jing Zhao,Liming Zhou,Xing-Jie Liang,Ju-Yoon Yoon +9 more
TL;DR: The use of boron dipyrromethene (BODIPY) in biomedicine is reviewed in this paper , where its synthesis and regulatory strategies are summarized, and inspiring cutting-edge work in post-functionalization strategies is highlighted.
Journal ArticleDOI
GlycoBODIPYs: Sugars Serving as a Natural Stock for Water-soluble Fluorescent Probes of Complex Chiral Morphology.
Lukas J. Patalag,Somayeh Ahadi,Olesia Lashchuk,Peter G. Jones,Simon Ebbinghaus,Daniel B. Werz +5 more
TL;DR: In this paper, a range of unprocessed, reducing sugar substrates (mono-, di-, and trisaccharides) are taken part in a straightforward four-step synthetic route to water-soluble, uncharged BODIPY derivatives with unimpaired chiral integrity and high fluorescence efficiency.
Journal ArticleDOI
A water-soluble turn-on fluorescent probe for rapid discrimination and imaging of Cys/Hcy and GSH in cells and zebrafish through different fluorescent channels
TL;DR: In this article , a simple water-soluble probe, PMCI, was developed for the first time to rapidly discriminate Cys/Hcy and GSH by dual excitation and emission wavelengths.
Journal ArticleDOI
Synthesis of Polycyclic Aromatic Hydrocarbons Decorated by Fluorinated Carbon Acids/Carbanions.
Shoki Hoshikawa,Hikaru Yanai,Irene Martín-Mejías,Carlos Lázaro-Milla,Cristina Aragoncillo,Pedro Almendros,Takashi Matsumoto +6 more
TL;DR: The carboarylation reaction of biphenyl-alkynes was successfully triggered by electrophilic attack of 1,1-bis(triflyl)ethylene on the alkyne moiety to give polycyclic aromatic hydrocarbons (PAHs) decorated by superacidic carbon acid functionality.
Journal ArticleDOI
Imaging of intracellular bisulfate based on sensitive ratiometric fluorescent probes
TL;DR: Wang et al. as discussed by the authors designed and synthesized three ratiometric fluorescent probes HNIC, CIVP and HVIC, which can image HSO3− in living cells.
References
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Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
TL;DR: Experimental and computational approaches to estimate solubility and permeability in discovery and development settings are described in this article, where the rule of 5 is used to predict poor absorption or permeability when there are more than 5 H-bond donors, 10 Hbond acceptors, and the calculated Log P (CLogP) is greater than 5 (or MlogP > 415).
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Electron affinities of the first-row atoms revisited. Systematic basis sets and wave functions
TL;DR: In this paper, a reliable procedure for calculating the electron affinity of an atom and present results for hydrogen, boron, carbon, oxygen, and fluorine (hydrogen is included for completeness).
Journal ArticleDOI
A survey of Hammett substituent constants and resonance and field parameters
Corwin Hansch,A. Leo,R. W. Taft +2 more
TL;DR: The Hammett equation has been widely used for the study and interpretation of organic reactions and their mechanisms as mentioned in this paper, and it is astonishing that u constants, obtained simply from the ionization of organic acids in solution, can frequently predict successfully equilibrium and rate constants for a variety of families of reactions in solution.
Journal ArticleDOI
BODIPY dyes and their derivatives: syntheses and spectroscopic properties.
Aurore Loudet,Kevin Burgess +1 more
Journal ArticleDOI
The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed
TL;DR: The Bodipy family, first developed as luminescent tags and laser dyes, has become a cornerstone for these new applications and the near future looks extremely bright for "porphyrin's little sister".