Fluorous Organic Hybrid Solvents for Non-Fluorous Organic Synthesis

Matsubara, Hiroshi; Ryu, Ilhyong

doi:10.1007/128_2011_250

Cited by 11 publications

(4 citation statements)

References 54 publications

(52 reference statements)

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“…Capello et al offered a relative definition of a green solvent: a green solvent is one that has a lower EHS impact and energy requirement during its LCA compared to conventional solvents. Currently, the main research areas of green solvents include supercritical fluids, − ionic liquids, − fluorous solvents, − hydrophobic deep eutectic solvents, − and biobased solvents. − …”

Section: Introductionmentioning

confidence: 99%

A Systematic Review on Intensifications of Artificial Intelligence Assisted Green Solvent Development

Wen,

Nan,

et al. 2023

Ind. Eng. Chem. Res.

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Solvents are indispensable components of chemical processes, and the application of ecofriendly, safe, and efficient solvents is vital for building green chemical processes. Nowadays, new techniques have been applied in discovering and exploring green solvents, among which artificial intelligence (AI) plays an increasingly important role in predicting their physical and chemical properties. Being able to explore the chemical space of green solvents, AI can also be utilized to screen out expected solvents and inversely design new solvents. This review introduces the application of AI assisted green solvent design, focusing on intensification techniques in the processes of green solvent design and property prediction. First, the various intensification techniques of quantitative structure−property relationships (QSPR) employed in the process of solvent property prediction are summarized, including the optimization and intensification of feature extraction, ensemble learning, uncertainty analysis, and interpretability modeling. After that, the basic principles and latest theoretical advances in the application of inverse molecular design for green solvents are reviewed, including high-throughput screening, computer-aided molecular design (CAMD), and deep generative models. Finally, new ideas are proposed for the improvement of each intensification technique in order to better match the high demands of the particular application in green solvent design.

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Section: Introductionmentioning

confidence: 99%

A Systematic Review on Intensifications of Artificial Intelligence Assisted Green Solvent Development

Wen,

Nan,

et al. 2023

Ind. Eng. Chem. Res.

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“…The best universal solvent for 2 – 7 was trifluorotoluene (Figure 2 B), a solvent often employed in fluoro-organic synthesis. 24 The affinity of the fluorofluorophores for fluorine-containing solvents was immediately evident when comparing their solubility in trifluorotoluene and toluene, where in the latter solvent the PL of 4 – 7 is quenched by aggregation (Figure 2 B/C). We assayed the solubility of 2 – 7 in six fluorous solvents: methoxyperfluorobutane, perfluorotripropylamine, perfluorooctyl iodide, perfluoromethylcyclohexane, perfluorodecalin, and perfluorohexanes ( Figure S2, Table S2 ).…”

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confidence: 97%

Fluorofluorophores: Fluorescent Fluorous Chemical Tools Spanning the Visible Spectrum

Sletten

Swager

2014

J. Am. Chem. Soc.

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“Fluoro” refers to both fluorescent and fluorinated compounds. Despite the shared prefix, there are very few fluorescent molecules that are soluble in perfluorinated solvents. This paucity is surprising, given that optical microscopy is a ubiquitous technique throughout the physical sciences and the orthogonality of fluorous materials is a commonly exploited strategy in synthetic chemistry, materials science, and chemical biology. We have addressed this shortage by synthesizing a panel of “fluorofluorophores,” fluorescent molecules containing high weight percent fluorine with optical properties spanning the visible spectrum. We demonstrate the utility of these fluorofluorophores by preparing fluorescent perfluorocarbon nanoemulsions.

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“…Usually such substitutions are carried out with an excess of butadiyne, a copper(I) catalyst, and a mixed solvent comprised of the base HNEt 2 and CH 2 Cl 2 21. However, given the poor solubilities of 8a-c in organic solvents, a "hybrid" organic/fluorous solvent,22,23 trifluorotoluene (CF 3 C 6 H 5 ), was used -7-in place of CH 2 Cl 2 . Such media are capable of dissolving appreciable concentrations of both fluorophilic and lipophilic solutes.…”

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confidence: 99%

A phase based approach to insulated molecular wires: Diplatinum octatetraynediyl complexes bearing fluorous trialkylphosphine ligands

Clough

Fiedler

Bhuvanesh

et al. 2016

Journal of Organometallic Chemistry

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Reactions of [(tetrahydrothiophene)Pt(C 6 F 5)µ-Cl] 2 and fluorous phosphines P((C-H 2) m R fn) 3 (R fn = (CF 2) n-1 CF 3 ; m/n = a, 2/8; b, 3/8; c, 3/10) afford the chloride complexes trans-(C 6 F 5)((R fn (CH 2) m) 3 P) 2 PtCl (8a-c, 40-74%), which upon treatment with butadiyne and CuI (cat.) in HNEt 2 /CF 3 C 6 H 5 give trans-(C 6 F 5)((R fn (CH 2) m) 3 P) 2 Pt(C≡C) 2 H (9a-c, 44-64%). Subsequent reactions with oxygen and CuCl/TMEDA in acetone yield the title complexes trans,trans-(C 6 F 5)((R fn (CH 2) m) 3 P) 2 Pt(C≡C) 4 Pt(P((CH 2) m R fn) 3) 2 (C 6 F 5) (10a-c, 35-52%). All platinum complexes exhibit CF 3 C 6 F 11 /toluene partition coefficients of >99:<1. The crystal structure of 8b shows that the perfluoroalkyl groups segregate into fluorous domains. It was therefore thought that the perfluoroalkyl groups in 10a-c would aggregate about the polyynediyl chain. However, these adducts could not be crystallized. Electrochemical oxidations of 10a-c give radical cations that are much less stable than trialkyl and triarylphosphine analogs.

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Fluorous Organic Hybrid Solvents for Non-Fluorous Organic Synthesis

Cited by 11 publications

References 54 publications

A Systematic Review on Intensifications of Artificial Intelligence Assisted Green Solvent Development

A Systematic Review on Intensifications of Artificial Intelligence Assisted Green Solvent Development

Fluorofluorophores: Fluorescent Fluorous Chemical Tools Spanning the Visible Spectrum

A phase based approach to insulated molecular wires: Diplatinum octatetraynediyl complexes bearing fluorous trialkylphosphine ligands

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