Binding of Amino Acids into a Novel Multiresponsive Ferrocene Receptor Having an Ene Backbone

Debroy, Paromita; Banerjee, Mohua; Prasad, M.; Moulik, Satya P.; Roy, Sujit

doi:10.1021/ol0476772

Cited by 39 publications

(18 citation statements)

References 24 publications

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“…The development of artificial receptors for amino acids is slow due to their hydrophilicity and bifunctional character. To our knowledge, there is only one example of a ferrocenebased redox receptor for amino acids, [20] which involves a ferrocene with two open arms bearing multipoint binding sites.…”

Section: Resultsmentioning

confidence: 99%

[3.3]Ferrocenophanes with Guanidine Bridging Units as Multisignalling Receptor Molecules for Selective Recognition of Anions, Cations, and Amino Acids

Otón

Espinosa

Tárraga

et al. 2007

Chemistry A European J

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The synthesis, electrochemical, and optical properties of a new [3.3]ferrocenophane framework in which two ferrocene subunits, with similar electronic environments, are linked through two substituted guanidine moieties, are reported. The receptors 4-7 have been prepared in good yields by the reaction of bis(carbodiimide) 3 with primary amines. This architecture is exceptionally "tunable" because a variety of "legs" may be appended to the basic [3.3]ferrocenophane scaffold to give a wide range of signaling units. These receptors show remarkable ion-sensing properties, due to the presence of a redox active unit (ferrocene), and an amphoteric binding site (guanidine). In this nitrogen-rich structural motif the guanidine bridges act as multipoint binding sites for anions, cations, and amino acids. Sensing of anions takes place both by unprecedented redox-ratiometric measurements (F-, Cl-, AcO-, NO3-, HSO4-, H2PO4-, and HP2O7(3-)), and colorimetric change (F-, AcO-, H2PO4-, and HP2O7(3-)). Sensing and discrimination of amino acids takes place by redox-ratiometric measurements, whereas the recognition of metal cations (Zn2+, Ni2+, and Cd2+) is achieved either by electrochemical or fluorescence measurements. Moreover, the reported receptors display splitting of the oxidation wave of the Fe(II)/Fe(III) redox couple, and form the mixed-valence species 4+* -7+* by electrochemical partial oxidation which, interestingly, show intervalence charge-transfer transitions associated to the appearance of absorption bands in the near infrared spectral region.

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Section: Resultsmentioning

confidence: 99%

[3.3]Ferrocenophanes with Guanidine Bridging Units as Multisignalling Receptor Molecules for Selective Recognition of Anions, Cations, and Amino Acids

Otón

Espinosa

Tárraga

et al. 2007

Chemistry A European J

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“…It is a dependable physical method to study the process of micellization [42]. There are numerous available literature that have used ITC for amphiphile aggregation [1][2][3][4][5]23,[31][32][33]35,[41][42][43][44][45][46][47], thermodynamics of bilayers-to-micelle transition [48,49], amphiphile interaction with polymers and macromolecules [50][51][52][53][54][55][56][57], characterization of protein solution [58], binding of small molecules with biopolymers [59][60][61], interaction of microemulsion with vesicles [62], determination of second virial coefficient of ionic liquid microemulsion [63], kinetics of reaction [64], etc. We have also used the method and have shown a general way of data treatment for microheterogeneous systems like micelles [65] and microemulsions [66].…”

Section: Calorimetrymentioning

confidence: 99%

Amphiphile self-aggregation: An attempt to reconcile the agreement–disagreement between the enthalpies of micellization determined by the van’t Hoff and Calorimetry methods

Moulik

Mitra

2009

Journal of Colloid and Interface Science

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“…Changes in the oxidation potential of ferrocene allows the electrochemical sensing of cations, anions, and neutral molecules, 1,2 and the coupling of the ''redox active'' ferrocene unit with a fluorescent group in the same molecule has led to the synthesis of multiresponsive receptors. 3,4 The biological activity of ferrocenyl analogues of established drugs (e.g.…”

Section: Introductionmentioning

confidence: 99%

Comparative HPLC enantioseparation of ferrocenylalcohols on two cellulose‐based chiral stationary phases

2007

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The direct HPLC enantiomeric separation of several ferrocenylalcohols on the commercially available Chiralcel OD and Chiralcel OJ columns has been evaluated in normal-phase mode. Almost all the compounds were resolved on one or both chiral stationary phases (CSPs) with separation factor (alpha) ranging from 1.06 to 2.88 while the resolution (R(s)) varied from 0.63 to 12.70 In the separation of the alpha-ferrocenylalcohols 1a-e and the phenyl analogues 2a-e, which were all resolved except 1c, a similar trend in the retention behavior for the two series of alcohols was evidenced and the selectivity was roughly complementary on the two investigated CSP. For three ferrocenylacohols, chosen as model compounds, the influence of the mobile phase composition and temperature on the enantioseparation were investigated and additional information on the chiral recognition mechanism were deduced from the chromatographic behavior of their acetylderivatives.

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Binding of Amino Acids into a Novel Multiresponsive Ferrocene Receptor Having an Ene Backbone

Cited by 39 publications

References 24 publications

[3.3]Ferrocenophanes with Guanidine Bridging Units as Multisignalling Receptor Molecules for Selective Recognition of Anions, Cations, and Amino Acids

[3.3]Ferrocenophanes with Guanidine Bridging Units as Multisignalling Receptor Molecules for Selective Recognition of Anions, Cations, and Amino Acids

Amphiphile self-aggregation: An attempt to reconcile the agreement–disagreement between the enthalpies of micellization determined by the van’t Hoff and Calorimetry methods

Comparative HPLC enantioseparation of ferrocenylalcohols on two cellulose‐based chiral stationary phases

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