Functionalized ionic liquids with highly polar polyhydroxylated appendages and their rapid synthesis via thiol-ene click chemistry

O’Brien, Richard A.; Mirjafari, Arsalan; Jajam, Vijayakumari; Capley, Erin N.; Stenson, Alexandra C.; West, Kevin N.; Davis, James H.

doi:10.1016/j.tetlet.2011.07.126

Cited by 22 publications

(18 citation statements)

References 15 publications

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“…The hydroxyl groups likely form an intermolecular hydrogen-bond network contributing to the increased viscosity. 74, 79, 105 As pointed out by Ma et al 106 using femtosecond time-resolved depleted spontaneous emission, the hydroxyl groups in IL cations induce an enhancement of local microviscosity leading to slow solvation and rotation dynamics of the probe molecule rhodamine 700 in the ILs studied. In addition, the longer the hydroxyl-terminated PEG chain, the higher the IL viscosity due to stronger van der Waals interactions in addition to hydrogen bonding, such as examples in Table 1 including (in increasing order of viscosity): 63 < 64 < 65 , 66 < 67 < 68 , 69 < 70 < 71 .…”

Section: Physicochemical Properties Of Ether- and Hydroxyl-functiomentioning

confidence: 89%

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Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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In recent years, the designer nature of ionic liquids (ILs) has driven their exploration and exploitation in countless fields among the physical and chemical sciences. A fair measure of the tremendous attention placed on these fluids has been attributed to their inherent designer nature. And yet, there are relatively few examples of reviews which emphasize this vital aspect in an exhaustive or meaningful way. In this critical review, we systematically survey the physicochemical properties of the collective library of ether- and alcohol-functionalized ILs, highlighting the impact of ionic structure on features such as viscosity, phase behavior/transitions, density, thermostability, electrochemical properties, and polarity (e.g., hydrophilicity, hydrogen bonding capability). In the latter portions of this review, we emphasize the attractive applications of these functionalized ILs across a range of disciplines, including their use as electrolytes or functional fluids for electrochemistry, extractions, biphasic systems, gas separations, carbon capture, carbohydrate dissolution (particularly, the (ligno)celluloses), polymer chemistry, antimicrobial and antielectrostatic agents, organic synthesis, biomolecular stabilization and activation, and nanoscience. Finally, this review discusses anion-functionalized ILs, including sulfur- and oxygen-functionalized analogs, as well as choline-based deep eutectic solvents (DESs), an emerging class of fluids which can be sensibly categorized as semi-molecular cousins to the IL. Finally, the toxicity and biodegradability of ether- and alcohol-functionalized ILs are discussed and cautiously evaluated in light of recent reports. By carefully summarizing literature examples on the properties and applications of oxy-functional designer ILs up till now, it is our intent that this review offer a barometer for gauging future advances in the field as well as a trigger to spur further contemplation of these seemingly inexhaustible and—relative to their potential—virtually untouched fluids. It is abundantly clear that these remarkable fluidic materials are here to stay, just as certain design rules are slowly beginning to emerge. However, in fairness, serendipity also still plays an undeniable role, highlighting the need for both expanded in silico studies and a beacon to attract bright, young researchers to the field.

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Section: Physicochemical Properties Of Ether- and Hydroxyl-functiomentioning

confidence: 89%

“…O’Brien et al 74 recently carried out the photoaddition of 1-thioglycerol to ene -type imidazolium salts via thiol–ene “click” chemistry (Scheme 8). The reaction was initiated by 2,2-dimethoxy-2-phenylacetophenone (DMPA) as the photo-initiator using a photochemical irradiation system.…”

Section: Preparation Of Ether- and Hydroxyl-functionalized Ilsmentioning

confidence: 99%

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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“…28 There was no report of incomplete functionalization when the 1-methyl-3-vinylimidazolium salt was used as a substrate for a click reaction with a hydrogenated aliphatic thiol, however. 12,29 Interestingly, the neutral vinylimidazole click product 9 was able to be synthesized and characterized with no evidence of oligomerization. This change in reactivity is hypothesized to result from the electrostatics of the species participating 11 in the reactions, due to the salts' greater partial positive charge on the vinyl functionality, as well as on the thiyl radical due to the electron withdrawing nature of the fluorine atoms.…”

Section: Synthesis and Purificationmentioning

confidence: 99%

“…9, 10 An area that is largely unexplored is the preparation of omniphobic ionic liquids using thiol-ene/yne click chemistry. 11,12 While there are already several commercially-available hydrophobic ionic liquids, they typically suffer from poor solubility in organic solvents. A synthetic strategy for obtaining hydrophobic ionic liquids is to incorporate fluorinated anions, 13 commonly bis(trifluoromethylsulfonyl)imide (Tf 2 N -) and hexafluorophosphate (PF 6 -), or cations with fluorinated arms or "ponytails."…”

Section: Introductionmentioning

confidence: 99%

Fluoroalkyl-functional imidazoles and imidazolium–based ionic liquids prepared via thiol-ene/yne click chemistry

Moore

Greeson

Redeker

et al. 2019

Journal of Molecular Liquids

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“…The C=C bond is also a versatile group that can be used to introduce other functional groups into the IL cation or to tether the IL onto suitable supports. It is possible to create structurally elaborated ILs through the thiol–ene reaction, for example, TSILs bearing up to eight hydroxy groups per cation have been prepared by the reaction of 1‐thioglycerol with vinyl‐ or allyl‐functionalized ILs in a single‐step process (Scheme ) 32…”

Section: Synthesis Of Task‐specific Ilsmentioning

confidence: 99%

Visible‐Light‐Mediated Addition of α‐Aminoalkyl Radicals to [60]Fullerene by Using Photoredox Catalysts

Miyake

Ashida

Nakajima

et al. 2014

Chemistry A European J

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The functionalization of fullerene has been extensively studied and various fullerene derivatives have been synthesized. We have succeeded in the functionalization of [60]fullerene by using α-aminoalkyl radicals generated by visible-light-mediated single-electron oxidation of α-silylamines as synthetic intermediates. In these reactions, the introduction of diarylamino groups, which are useful electron donors, has been easily achieved.

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Functionalized ionic liquids with highly polar polyhydroxylated appendages and their rapid synthesis via thiol-ene click chemistry

Cited by 22 publications

References 15 publications

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Fluoroalkyl-functional imidazoles and imidazolium–based ionic liquids prepared via thiol-ene/yne click chemistry

Visible‐Light‐Mediated Addition of α‐Aminoalkyl Radicals to [60]Fullerene by Using Photoredox Catalysts

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