Branched polyfluorinated triflate—An easily available polyfluoroalkylating agent

Kaplánek, Robert; Břı́za, Tomáš; Havlík, Martin; Dolenský, Bohumil; Kejík, Zdeněk; Martásek, Pavel; Král, Vladimı́r

doi:10.1016/j.jfluchem.2005.12.031

Cited by 9 publications

(6 citation statements)

References 27 publications

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“…It was anticipated that thiol 14 can be assembled from triflate 15, which is known to be accessible in five steps from commercially available starting materials. [23] The starting point for the synthesis of building block 16 is tribromide 18. Monothiolation, introduction of the fluorous ponytails in an S N 2 reaction, and the deprotection step represent the pathway to building block 16.…”

Section: Synthetic Strategymentioning

confidence: 99%

“…Starting from 3-(perfluorohexyl)propyl iodide and diethyl malonate, triflate 15 was assembled in five steps according to a literature procedure. [23] This literature protocol yields triflate 15 in a high overall yield of 80 % over the five steps including only two purification steps. With the triflate in hand, the sulfur can be efficiently introduced as a trityl-protected functionality by the reaction of triflate 15 with trityl thiol and an excess amount of sodium hydride stirred in THF at room temperature for two hours.…”

Section: Synthesismentioning

confidence: 99%

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Highly Fluorous Porphyrins as Model Compounds for Molecule Interferometry

et al. 2011

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The synthesis and characterization of seven tailor‐made highly fluorous porphyrin derivatives are described, as large perfluoroalkyl‐functionalized organic molecules are the most complex objects for which the quantum wave nature has been observed so far. We have found, in particular, that tetrakis(pentafluorophenyl)porphyrin is a suitable starting point for a modular synthesis that is geared towards porphyrin derivatives with many peripheral fluorous chains. This allows us to tailor and optimize the sublimation features of these compounds for molecule interferometry. We have analyzed the evaporation process of one member of the series by determining the enthalpy of evaporation, as the creation of a sufficiently intense, slow molecular beam is crucial for quantum interference experiments. We present the quantum fringe pattern of a second member of the series, which we could obtain in a Kapitza–Dirac–Talbot–Lau interferometer.

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Section: Synthetic Strategymentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Highly Fluorous Porphyrins as Model Compounds for Molecule Interferometry

et al. 2011

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“…The monoacid 1 was prepared starting from substitution of a malonic ester with two fluorinated alkyl chains, followed by saponification of the esters and decarboxylation of the resulting diacid 2 (Scheme 1). 60,61 The alcohol 3 was obtained in high yield by reduction of the monoacid 1 in anhydrous THF with the BH 3 $THF complex as reducing agent. This alcohol was reacted with phthalimide under Mitsunobu conditions to form the phthalimide derivative 4.…”

Section: Experimental Synthesis Of Pdi With Branched Perfluorinated S...mentioning

confidence: 99%

Phase separation and affinity between a fluorinated perylene diimide dye and an alkyl-substituted hexa-peri-hexabenzocoronene

et al. 2010

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Fluorination of alkyl groups is a known strategy for hindering miscibility, thus promoting phase separation, when blends are prepared with a hydrocarbon compound. A new perylene bis(dicarboximide) derivative functionalized with branched N-perfluoroalkyl moieties (BPF-PDI) has been synthesized as electron acceptor to be potentially used in conjunction with the electron donor hexakis(dodecyl)hexabenzocoronene (HBC-C 12 ) in bulk heterojunction solar cells. Aiming at controlling self-assembly between the two components at the supramolecular level, stoichiometric blends in CHCl 3 have been prepared either by spin-or drop-casting onto silicon surfaces, and further subjected to solvent vapour annealing (SVA) treatment in a CHCl 3 -saturated atmosphere. Spectroscopic investigation in solution shows the formation of supramolecular BPF-PDI-HBC-C 12 dimers, with an association constant K ass ¼ (2.1 AE 0.3) Â 10 4 M À1 , pointing to a strong and unexpected affinity between the two species within the mixture. Characterization through optical and atomic force microscopies of the deposited samples revealed that the self-assembly behaviour of the blends on SiO x is remarkably different from mono-component films, thus confirming the absence of a macroscopic phase-separation between the two components featuring isolated domains of the neat acceptor or donor compound. In addition, X-ray studies provided evidence for the existence of a local-scale phase separation. These findings are of importance for organic photovoltaics, since they offer a new strategy to control the phase separation at different scales in electron acceptor-donor blends.

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“…Previously reported strategies to access branched C 6 F 13 tags include malonate alkylation, , Grignard addition, , and sequential iodo-ene/elimination reactions , (Figure A). Perfluorinated tert -butyl groups have also been investigated as biocompatible fluorous tags through the addition of perfluoro- tert -butoxide. , Collectively, these approaches have validated the use of short fluorous segments to impart solubility in perfluorocarbons; yet, there remains no tag that can easily be appended to compounds with a variety of different chemistries.…”

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confidence: 99%

A General Approach to Biocompatible Branched Fluorous Tags for Increased Solubility in Perfluorocarbon Solvents

Miller

Sletten

2018

Org. Lett.

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A modular, cost-effective route to a library of branched fluorous tags with two short, biocompatible, fluorinated chains (C6F13) is reported. These branched fluorous tags provide high fluorous content without the use of long-chain linear perfluorocarbons (e.g. perfluorooctanoic acid), which have rising health concerns due to their bioaccumulation. By attaching these tags to a porphyrin, it is demonstrated that high solubility can be achieved in fluorous solvents that are readily cleared from mammals. This work enhances the biocompatibility of perfluorocarbon nanoemulsions for photodynamic therapy.

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Branched polyfluorinated triflate—An easily available polyfluoroalkylating agent

Cited by 9 publications

References 27 publications

Highly Fluorous Porphyrins as Model Compounds for Molecule Interferometry

Highly Fluorous Porphyrins as Model Compounds for Molecule Interferometry

Phase separation and affinity between a fluorinated perylene diimide dye and an alkyl-substituted hexa-peri-hexabenzocoronene

A General Approach to Biocompatible Branched Fluorous Tags for Increased Solubility in Perfluorocarbon Solvents

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