Exploiting isohexide scaffolds for the preparation of chiral ionic liquids tweezers

Zullo, Valerio; Górecki, Marcin; Guazzelli, Lorenzo; Mezzetta, Andrea; Iuliano, Anna

doi:10.1016/j.molliq.2020.114528

Cited by 14 publications

(23 citation statements)

References 72 publications

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“…To conclude, a comparison between the two works clearly shows that the dicationic compounds, reported by Zullo et al [ 70 ] are by far more stable than the ones reported by M’Sahel et al [ 68 ]. This result could be ascribed to different aspects; in particular, compounds 83 and 84 possess no free hydroxyl group and a positive charge far from the sugar core.…”

Section: Thermal Analysismentioning

confidence: 64%

“…Following this idea, in 2020, Zullo et al [ 70 ] developed a different strategy for synthesizing new ILs starting from isomannide and isosorbide. ( Scheme 18 ) In their work, the authors preserved the native stereochemistry of the parent sugar derivative: In particular, isomannide and isosorbide were converted into the 6-quinolinic carboxylic diesters 81 and 82 with a simple double esterification reaction in the presence of N- (3-dimethylaminopropyl)- N ′-ethylcarbodiimide (EDC) and 4-dimethylamino pyridine (DMAP) ( Scheme 18 ).…”

Section: Synthesismentioning

confidence: 99%

“…Since 2011, the thermal analysis of isohexide-derived ILs was reported only in two works [ 68 , 70 ]. In the first one [ 68 ], M’Sahel et al analyzed some triazolium containing RTILs possessing the stereochemistry of isomannide or isoidide.…”

Section: Thermal Analysismentioning

confidence: 99%

“…In the second work [ 70 ], Zullo et al analyzed new ILs possessing isomannide and isosorbide stereochemistry. ( Table 5 ) Compounds 83a,b and 84a ( Figure 8 ), containing iodide as the anion, where all solids at room temperature and did not show a melting temperature in the explored range, since they all degraded before melting.…”

Section: Thermal Analysismentioning

confidence: 99%

“…Sugar-based ILs are not intrinsically thermally unstable, as it could be assumed from the general knowledge of sugar reactivity. Depending on the structure and on the protecting group pattern, stability as high as 370.7 °C (IL 85a [ 70 ], based on the onset temperature) has been observed. On the other hand, attention should be paid to the melting point of these structures to possibly classify them as IL with full rights, as the threshold of 100 °C has been exceeded in several cases.…”

Section: Thermal Analysismentioning

confidence: 99%

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Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

2021

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Carbohydrates represent a promising option in transitioning from oil-based chemical resources to renewable ones, with the goal of developing chemistries for a sustainable future. Cellulose, hemicellulose, and largely available monosaccharides already provide useful chemical building blocks, so-called platform chemicals, such as levulinic acid and hydroxymethyl furfural, as well as solvents like cyrene or gamma-valerolactone. Therefore, there is great anticipation for novel applications involving materials and chemicals derived from sugars. In the field of ionic liquids (ILs), sugar-based ILs have been overlooked for a long time, mainly on account of their multistep demanding preparation. However, exploring new strategies for accessing sugar-based ILs, their study, and their exploitation, are attracting increasing interest. This is due to the growing concerns about the negative (eco)toxicity profile of most ILs in conjunction with their non-sustainable nature. In the present review, a literature survey concerning the development of sugar-based ILs since 2011 is presented. Their preparation strategies and thermal behavior analyses, sorted by sugar type, make up the first two sections with the intention to provide the reader with a useful guide. A final overview of the potential applications of sugar-based ILs and their future perspectives complement the present analysis.

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Section: Thermal Analysismentioning

confidence: 64%

Section: Synthesismentioning

confidence: 99%

Section: Thermal Analysismentioning

confidence: 99%

Section: Thermal Analysismentioning

confidence: 99%

Section: Thermal Analysismentioning

confidence: 99%

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Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

2021

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Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources

Zullo

Iuliano

Zinna

2022

Chemistry A European J

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Organic compounds showing circularly polarized luminescence (CPL) are at the forefront of novel applications and technologies. Here we show the synthesis and chiroptical properties of pyrene and perylene derivatives of inexpensive chiral scaffolds: isomannide and isosorbide. Low‐intensity ECD spectra were obtained, suggesting the absence of chromophore interaction in the ground state, except in the case of isomannide bis‐perylenecarboxylate, whose ECD spectrum showed a positive exciton couplet. All isomannide derivatives, with the only exception of the one containing a pyrenecarboxylate and a perylenecarboxylate, exhibited excimer CPL spectra, whereas isosorbide derivatives did not show any CPL. Isomannide derivatives bearing two pyrenecarboxylate or two pyrenylacetate groups showed positive CPL emission with dissymmetry factors up to 10−2, which depends on the conformational freedom of the appended units. The CPL sign, Stokes shift and order of magnitude of dissymmetry factor were reproduced by excited‐state calculations on a representative compound. Interestingly, the mixed derivative containing pyrenic units with different spacing from the isomannide scaffold showed an oppositely signed excimer band with respect to the homo‐substituted derivatives.

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