Self‐Propagated <i>para</i>‐Fluoro‐Thiol Reaction

Cavalli, Federica; Bloesser, Fabian R.; Barner‐Kowollik, Christopher; Barner, Leonie

doi:10.1002/chem.201901290

Cited by 11 publications

(2 citation statements)

References 29 publications

(67 reference statements)

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“…[ 21 ] Hence, the PFTR proceeds under comparably mild conditions and orthogonal to other nucleophiles, specifically targeting accessible thiols. [ 22 ] The progress of the reaction is macroscopically visible by a color change of the reaction mixture as seen for instance for the reaction of StyPy (1.0 equiv., 5 mg·mL −1 ) with the thiol‐containing amino acid cysteine (1.0 equiv.) in the presence of the base DBU (1,8‐diazabicyclo(5.4.0)undec‐7‐ene, 2.0 equiv.).…”

Section: Resultsmentioning

confidence: 99%

A Modular Fluorescent Probe for Viscosity and Polarity Sensing in DNA Hybrid Mesostructures

et al. 2020

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There exists a critical need in biomedical molecular imaging and diagnostics for molecular sensors that report on slight changes to their local microenvironment with high spatial fidelity. Herein, a modular fluorescent probe, termed StyPy, is rationally designed which features i) an enormous and tunable Stokes shift based on twisted intramolecular charge transfer (TICT) processes with no overlap, a broad emission in the far‐red/near‐infrared (NIR) region of light and extraordinary quantum yields of fluorescence, ii) a modular applicability via facile para‐fluoro‐thiol reaction (PFTR), and iii) a polarity‐ and viscosity‐dependent emission. This renders StyPy as a particularly promising molecular sensor. Based on the thorough characterization on the molecular level, StyPy reports on the viscosity change in all‐DNA microspheres and indicates the hydrophilic and hydrophobic compartments of hybrid DNA‐based mesostructures consisting of latex beads embedded in DNA microspheres. Moreover, the enormous Stokes shift of StyPy enables one to detect multiple fluorophores, while using only a single laser line for excitation in DNA protocells. The authors anticipate that the presented results for multiplexing information are of direct importance for advanced imaging in complex soft matter and biological systems.

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Section: Resultsmentioning

confidence: 99%

A Modular Fluorescent Probe for Viscosity and Polarity Sensing in DNA Hybrid Mesostructures

et al. 2020

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“…The para-uoro-thiol reaction (PFTR), another member of the click reaction family, also play an important role in polymer chemistry. [176][177][178] Very recently, our group applied this reaction for the synthesis of three-arm star polymers by employing a trifunctional pentauorobenzyl (3PFB) linker along with a poly(ethylene glycol) bearing a thiol end-group, and determined the number of PFTR events forming the polymer arm using a chemiluminescence (CL) read out (Scheme 1B). 179 In PFTR, a thiol is deprotonated by a base and subsequently reacts with the para-carbon of a PFB moiety, releasing a uoride ion.…”

Section: Polymer Architecturementioning

confidence: 99%

Fluorescence-readout as a powerful macromolecular characterisation tool

Wu,

Barner-Kowollik

2023

Chem. Sci.

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Post‐Polymerization Strategy via Dual Site Clicking for Synthesizing Intrinsically Cross‐Linkable Semiconducting Polymers

Lee,

Kang,

Lee

et al. 2024

EcoMat

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Crosslinked organic semiconductors have opened the way for various fabrication techniques in the field of organic electronics owing to their three‐dimensional network structure with high solvent resistivity. However, recent efforts to synthesize cross‐linkable semiconducting polymers have been limited by their low molecular weights and yields. In this study, this limitation is overcome by a novel post‐polymerization strategy. A reagent with a cross‐linkable functional group, (3‐mercaptopropyl)trimethoxysilane, is attached to a diketopyrrolopyrrole‐based donor–acceptor copolymer (DPPTT) via thioesterification and para‐fluoro‐thiol reaction, modifying two sites simultaneously. This modification preserves the molecular weight and electrical properties of the original polymers. In addition, the use of click chemistry enables high yield (98%) without any purification. The modified DPPTT demonstrated high resistance to organic solvents (80% retention dipped in 1‐chlorobenzene for 1 h). Exploiting this benefit, an ultrathin flexible array of 100 organic field‐effect transistors fabricated using conventional photolithography showed high‐performance reliability. Thus, this study provides a universal strategy to synthesize versatile polymer semiconductors for practical organic electronics. image

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Self‐Propagated para‐Fluoro‐Thiol Reaction

Cited by 11 publications

References 29 publications

A Modular Fluorescent Probe for Viscosity and Polarity Sensing in DNA Hybrid Mesostructures

A Modular Fluorescent Probe for Viscosity and Polarity Sensing in DNA Hybrid Mesostructures

Fluorescence-readout as a powerful macromolecular characterisation tool

Post‐Polymerization Strategy via Dual Site Clicking for Synthesizing Intrinsically Cross‐Linkable Semiconducting Polymers

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