Separation of halogenated benzenes enabled by investigation of halogen–π interactions with carbon materials

Kanao, Eisuke; Morinaga, Takashi; Kubo, Takuya; Naito, Toyohiro; Matsumoto, Takatoshi; Sano, Tomoharu; Maki, Hideshi; Yan, Mingdi; Otsuka, Koji

doi:10.1039/c9sc04906a

Cited by 18 publications

(16 citation statements)

References 75 publications

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“…Very recently, Kubo and co-workers experimentally evaluated the strength of the X- interaction between carbon-materials and a series of halogenated benzenes under NP elution conditions [8], assuming that the hydrophobic interaction was completely suppressed in this environment. Under this conditions, higher retentions were observed as the number of Cl, Br, or I substituents on the benzenes increased, especially for the C70-coated column 40 (Fig.…”

Section: Halogen Bond In Normal Phase Liquid Chromatographymentioning

confidence: 99%

“…When molecules are at work to carry out a specific function in molecular and supramolecular systems, they relate to each other by means of noncovalent interactions [4,5], which represent the essential elements of the code by which molecules are able to transfer the information contained in their structure [6]. These molecular relationships underlie mechanisms in several fields [7], and also makenoncovalent interactions a modern tool for design, preparation and function of advanced processes and materials in separation science [8].…”

Section: Introductionmentioning

confidence: 99%

“…Among noncovalent interactions, in the last decades halogen bonds (XBs) have found practical applications in several fields covering catalysis, crystal engineering, functional and soft materials, molecular recognition, supramolecular chemistry and biological, medicinal and pharmaceutical chemistry [9][10][11]. Nevertheless, separation processes promoted by XB are reported in smaller degree [8,[12][13][14][15][16]. In particular, despite the pivotal role of noncovalent interactions in LC enantiomer distinction [17,18], surprisingly, for a long time XBs were unexplored in the enantioseparation science [19].…”

Section: Introductionmentioning

confidence: 99%

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Halogen bond in separation science: A critical analysis across experimental and theoretical results

Peluso

Mamane

Dessì

et al. 2020

Journal of Chromatography A

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The halogen bond (XB) is a noncovalent interaction involving a halogen acting as electrophile and a Lewis base. In the last decades XB has found practical application in several fields. Nevertheless, despite the pivotal role of noncovalent interactions in separation science, investigations of XB in this field are still in their infancy, and so far a limited number of studies focusing on solid phase extraction, liquid-liquid microextraction, liquid-phase chromatography, and gas chromatography separation have been published. In addition, in the last few years, our groups have been systematically studying the potentiality of XB for HPLC enantioseparations. On this basis, in the present paper up-to-date results emerging from focused experiments and theoretical analyses performed by our laboratories are integrated with a descriptive presentation of XB features and the few studies published until now in separation science, with the aims to provide a comprehensive and critical discussion of the topic, and account for some still open issues in this field.

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Section: Halogen Bond In Normal Phase Liquid Chromatographymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Halogen bond in separation science: A critical analysis across experimental and theoretical results

Peluso

Mamane

Dessì

et al. 2020

Journal of Chromatography A

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“…C60-or C70-conjugated molecules were successfully synthesized using the methods of our previous studies 41,43 . Then, C60-or C70-bonded silica monolithic capillaries (C60 column or C70 column) were also prepared (see Scheme S1, S2, and Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Previously, we successfully prepared C 60 - or C 70 -fullerene (C60, C70) bonded separation media using a silica monolithic capillary and a thermo-reactive agent, perfluorophenyl azide. Then, the specific π interactions were identified for spherical recognition 37 – 40 , CH–π interaction 41 , 42 , and halogen–π interaction 43 , 44 . According to these effective intermolecular recognitions, we anticipated that the fullerene-bonded separation media might be useful for the separation of saccharides via the CH– or OH–π interaction as well as dipole interaction.…”

Section: Introductionmentioning

confidence: 99%

Separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography

Kobayashi

Okada

Tokuda

et al. 2020

Sci Rep

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We report on a potential method to separate sugars by using the specific interaction between fullerenes and saccharides in liquid chromatography (LC). Aromatic rings with high electron density are believed to interact strongly with saccharides due to CH-π and/or OH-π interactions. In this study, the fullerene-bonded columns were used to separate saccharides by LC under aqueous conditions. As a result, 2-aminobenzamide-labeled glucose homopolymer (Glcs) was effectively separated by both C60 and C70 columns in the range of Glc-1 to Glc-20 and high blood glucose level being retained in greater quantity. Furthermore, similar separations were identified by LC-mass spectrometry with nonlabeled glucose homopolymers. Theoretical study based on molecular dynamics and DFT calculation demonstrated that a supramolecular complex of saccharide-fullerene was formed through CH-π and/or OH-π interactions, and that the interactions between saccharide and fullerene increase with the increase units of the saccharide. Additionally, the C60 column retained disaccharides containing maltose, trehalose, and sucrose. In this case, it was assumed that the retention rates were determined by the difference of the dipole moment in each saccharide. These results suggest that the dipoleinduced dipole interaction was dominant, and that maltose-with the higher dipole moment-was more strongly retained compared to other disaccharides having lower dipole moment.

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Dual Cooperatively Grown J‐aggregates with Different Nucleus Size

et al. 2022

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A molecule featuring two distinct cooperatively grown J-aggregates is investigated. Interestingly, when cooling a hot monomer solution, the thermodynamically less stable J 1 is exclusively formed even at a particularly slowed temperature dropping rate, which transforms to the more stable J 2 at room temperature with very slow kinetics. This observation is ascribed to the differed nucleus sizes of J 1 and J 2 . During the cooling process, smaller J 1 nuclei are formed first at a higher temperature, favored by the entropy effect. At intermediate temperatures, the elongation of J 1 outcompetes the nucleation of J 2 . Then, below the elongation temperature of J 2 , the formation of this thermodynamically stable aggregate is hindered kinetically, due to the depletion of monomer by the slow dissociation of J 1 . Additional evidence proving the larger nucleus size of J 2 is also identified with the varied-temperature spectral analyses and mathematic simulations.

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Separation of halogenated benzenes enabled by investigation of halogen–π interactions with carbon materials

Abstract: We report the existence of bimodal interactions, the π–π and halogen–π interactions, between the halogenated benzenes and aromatic materials.

Cited by 18 publications

References 75 publications

Halogen bond in separation science: A critical analysis across experimental and theoretical results

Halogen bond in separation science: A critical analysis across experimental and theoretical results

Separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography

Dual Cooperatively Grown J‐aggregates with Different Nucleus Size

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