Komplexierung von Methan und Fluorchlorkohlen‐wasserstoffen durch Cryptophan‐A in organischer Lösung

Garel, Laurent; Dutasta, Jean‐Pierre; Collet, André

doi:10.1002/ange.19931050835

Cited by 43 publications

(38 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[1][2][3][4][5][6][7][8][9] It allows for a puristic understanding of the solvophobic driving force for the formation of discrete host-guest complexes [10] and has additional potential for gas storage, uptake, and separation, thus complementing solid-state applications of porous materials [11,12] or surface-immobilized macrocycles. [1][2][3][4][5][6][7][8][9] It allows for a puristic understanding of the solvophobic driving force for the formation of discrete host-guest complexes [10] and has additional potential for gas storage, uptake, and separation, thus complementing solid-state applications of porous materials [11,12] or surface-immobilized macrocycles.…”

mentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8][9] It allows for a puristic understanding of the solvophobic driving force for the formation of discrete host-guest complexes [10] and has additional potential for gas storage, uptake, and separation, thus complementing solid-state applications of porous materials [11,12] or surface-immobilized macrocycles. [14] Subsequently, synthetic hosts such as cryptophanes, [1] self-assembling capsules, [2][3][4][5] and hemicarcerands [6,7] have been investigated for their potential to entrap small hydrocarbons. [14] Subsequently, synthetic hosts such as cryptophanes, [1] self-assembling capsules, [2][3][4][5] and hemicarcerands [6,7] have been investigated for their potential to entrap small hydrocarbons.…”

mentioning

confidence: 99%

“…While a CB5 derivative has been reported to bind very small guests such as methane and acetylene, [12, 19] the homologue which holds most promise for hydrocarbon binding is CB6, [20] the original cucurbituril, which possesses an intermediary size to allow inclusion of guests with up to seven heavy atoms into its inner cavity. [1][2][3][4][5][6][7][8][9] The binding of xenon with CB6 has been studied by 129 Xe NMR spectroscopy in the presence of 0.2 m Na 2 SO 4 , [23] where the solubility is increased (but where also the binding strength suffers). [21,22] In particular, it prevents 1 H NMR titrations, which have been routinely employed in all previous studies on solution-phase gas binding by molecular containers.…”

mentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8][9] The binding of xenon with CB6 has been studied by 129 Xe NMR spectroscopy in the presence of 0.2 m Na 2 SO 4 , [23] where the solubility is increased (but where also the binding strength suffers). [1][2][3][4][5][6][7][8][9] In the quest for a convenient method to monitor volatile hydrocarbon binding to CB6, we selected an indicator displacement strategy [25] based on our recently developed anchor dye approach. [24] The binding constants, which we report herein for several simple hydrocarbons, are much larger than those observed for xenon, and, in fact, the largest ones reported for neutral guests with CB6.…”

mentioning

confidence: 99%

“…[21,22] In particular, it prevents 1 H NMR titrations, which have been routinely employed in all previous studies on solution-phase gas binding by molecular containers. [1][2][3][4][5][6][7][8][9] The binding of xenon with CB6 has been studied by 129 Xe NMR spectroscopy in the presence of 0.2 m Na 2 SO 4 , [23] where the solubility is increased (but where also the binding strength suffers). Alternatively, an alkylated CB6 derivative with higher water solubility has been employed, which was also investigated by isothermal titration calorimetry, to afford a binding constant of 3400 m À1 with xenon.…”

mentioning

confidence: 99%

See 4 more Smart Citations

Strong Binding of Hydrocarbons to Cucurbituril Probed by Fluorescent Dye Displacement: A Supramolecular Gas‐Sensing Ensemble

Florea¹,

Nau²

2011

Angewandte Chemie

View full text Add to dashboard Cite

The inclusion of small hydrocarbons into molecular container compounds in solution has received considerable attention. [1][2][3][4][5][6][7][8][9] It allows for a puristic understanding of the solvophobic driving force for the formation of discrete host-guest complexes [10] and has additional potential for gas storage, uptake, and separation, thus complementing solid-state applications of porous materials [11,12] or surface-immobilized macrocycles. [13] Studies on the precipitation of complexes between the smallest alkanes with a-cyclodextrin date back to the 1950s. [14] Subsequently, synthetic hosts such as cryptophanes, [1] self-assembling capsules, [2][3][4][5] and hemicarcerands [6,7] have been investigated for their potential to entrap small hydrocarbons. Herein, we describe a highly sensitive fluorescence-based method for the quantification of volatile hydrocarbons binding with cucurbituril. We observe exceptionally strong, highly selective, and reversible binding in aqueous solution.Cucurbit[n]urils (CBn) are water-soluble, highly symmetric pumpkin-shaped synthetic macrocycles, [15,16] and their unique supramolecular chemistry is presently unfolding. [17,18] They are well-established to bind organic ammonium ions through a combination of hydrophobic interactions inside the nonpolar inner cavity and ion-dipole interactions with the carbonyl portals. While a CB5 derivative has been reported to bind very small guests such as methane and acetylene, [12, 19] the homologue which holds most promise for hydrocarbon binding is CB6, [20] the original cucurbituril, which possesses an intermediary size to allow inclusion of guests with up to seven heavy atoms into its inner cavity. [18,21] Unfortunately, CB6 has an intrinsically low water solubility of about 30 mm, which complicates the determination of actual binding constants. [21,22] In particular, it prevents 1 H NMR titrations, which have been routinely employed in all previous studies on solution-phase gas binding by molecular containers. [1][2][3][4][5][6][7][8][9] The binding of xenon with CB6 has been studied by 129 Xe NMR spectroscopy in the presence of 0.2 m Na 2 SO 4 , [23] where the solubility is increased (but where also the binding strength suffers). Alternatively, an alkylated CB6 derivative with higher water solubility has been employed, which was also investigated by isothermal titration calorimetry, to afford a binding constant of 3400 m À1 with xenon. [24] The binding constants, which we report herein for several simple hydrocarbons, are much larger than those observed for xenon, and, in fact, the largest ones reported for neutral guests with CB6. [18] In several cases, they exceed those previously observed for any molecular container. [1][2][3][4][5][6][7][8][9] In the quest for a convenient method to monitor volatile hydrocarbon binding to CB6, we selected an indicator displacement strategy [25] based on our recently developed anchor dye approach. [26] In detail, compound 1 possesses a putrescine anchor for strong binding with CB6, [27] and a ...

show abstract

mentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8][9] It allows for a puristic understanding of the solvophobic driving force for the formation of discrete host-guest complexes [10] and has additional potential for gas storage, uptake, and separation, thus complementing solid-state applications of porous materials [11,12] or surface-immobilized macrocycles. [14] Subsequently, synthetic hosts such as cryptophanes, [1] self-assembling capsules, [2][3][4][5] and hemicarcerands [6,7] have been investigated for their potential to entrap small hydrocarbons. [14] Subsequently, synthetic hosts such as cryptophanes, [1] self-assembling capsules, [2][3][4][5] and hemicarcerands [6,7] have been investigated for their potential to entrap small hydrocarbons.…”

mentioning

confidence: 99%