Interaction of semicarbazide and thiosemicarbazide pyrene derivatives with anionic and cationic micelles: changed character of pyrene due to alteration in charge density induced by the side chains

Maity, Arnab; Das, Shrabanti; Mandal, Soumik; Gupta, Parna; Purkayastha, Pradipta

doi:10.1039/c3ra41029c

Cited by 5 publications

(7 citation statements)

References 26 publications

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“…For example, Pal et al report that some fluorescent 3H-indoles are able to recognize two different sites in SDS micelles, while only one type of locus is observed in the case of CTAB micelles [136]. Another very popular fluorescent molecular probe is pyrene [137]. Thiosemicarbazide and thiosemicarbazide pyrene derivatives are also used for examining CTAB and SDS micelles [137].…”

Section: Hydrogen Bonding Of the Solvatochromic Betaine Dyes In Surfa...mentioning

confidence: 99%

“…Another very popular fluorescent molecular probe is pyrene [137]. Thiosemicarbazide and thiosemicarbazide pyrene derivatives are also used for examining CTAB and SDS micelles [137]. The location of pyrene in surfactant micelles will be considered in Section 9.…”

Section: Hydrogen Bonding Of the Solvatochromic Betaine Dyes In Surfa...mentioning

confidence: 99%

“…Fluorescent dyes are another important group of molecular probes [22][23][24][25][26][27][28][29][30][31]130,131,134,149,[237][238][239][240][241]. An example of a fluorescent molecular probe that is not a dye in the traditional sense is the above mentioned pyrene [137]. Its solubility in aqueous micellar solutions is almost five orders of magnitude higher than in water [242].…”

Section: Some Other Reporter Moleculesmentioning

confidence: 99%

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Solvatochromic and Acid–Base Molecular Probes in Surfactant Micelles: Comparison of Molecular Dynamics Simulation with the Experiment

Mchedlov‐Petrossyan

Farafonov

Lebed

2023

Liquids

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This article summarizes a series of seventeen publications by the authors devoted to molecular dynamics modeling of various indicator dyes (molecular probes) enclosed in surfactant micelles. These dyes serve as generally recognized tools for studying various types of organized solutions, among which surfactant micelles in water are the simplest and most explored. The modeling procedure involves altogether 50 to 95 surfactant molecules, 16 to 28 thousand water molecules, and a single dye molecule. The presentation of the simulation results was preceded by a brief review of the state of experimental studies. This article consists of three parts. First, despite numerous literature data devoted to modeling the micelles itself, we decided to revisit this issue. The structure and hydration of the surface of micelles of surfactants, first of all of sodium n-dodecylsulfate, SDS, and cetyltrimethylammonium bromide, CTAB, were studied. The values of the electrical potential, Ψ, were estimated as functions of the ionic strength and distance from the surface. The decrease in the Ψ value with distance is gradual. Attempts to consider both DS− and CTA+ micelles in water without counterions result in a decay into two smaller aggregates. Obviously, the hydrophobic interaction (association) of the hydrocarbon tails balances the repulsion of the charged headgroups of these small “bare” micelles. The second part is devoted to the study of seven pyridinium N-phenolates, known as Reichardt’s dyes, in ionic micelles. These most powerful solvatochromic indicators are now used for examining various colloidal systems. The localization and orientation of both zwitterionic and (colorless) cationic forms are generally consistent with intuitive ideas about the hydrophobicity of substituents. Hydration has been quantitatively described for both the dye molecule as a whole and the oxygen atom. A number of markers, including the visible absorption spectra of Reichardt’s dyes, enable assuming a better hydration of the micellar surface of SDS than that of CTAB. However, our data show that it is more correct to speak about the more pronounced hydrogen-bonding ability of water molecules in anionic micelles than about better hydration of the SDS micelles as compared to CTAB ones. Finally, a set of acid–base indicators firmly fixed in the micellar pseudophase were studied by molecular dynamics. They are instruments for estimating electrostatic potentials of micelles and related aggregates as Ψ= 2.303RTF−1 (pKai − pKaapp), where pKai and pKaapp are indices of so-called intrinsic and apparent dissociation constants. In this case, in addition to the location, orientation, and hydration, the differences between values of pKaapp and indices of the dissociation constants in water were estimated. Only a semi-quantitative agreement with the experimental data was obtained. However, the differences between pKaapp of a given indicator in two micellar solutions do much better agree with the experimental data. Accordingly, the experimental Ψ values of ionic micelles, as determined using the pKaapp in nonionic micelles as pKai, are reproduced with reasonable accuracy for the corresponding indicator. However, following the experimental data, a scatter of the Ψ values obtained with different indicators for given micelles is observed. This problem may be the subject of further research.

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Section: Hydrogen Bonding Of the Solvatochromic Betaine Dyes In Surfa...mentioning

confidence: 99%

Section: Hydrogen Bonding Of the Solvatochromic Betaine Dyes In Surfa...mentioning

confidence: 99%

Section: Some Other Reporter Moleculesmentioning

confidence: 99%

See 1 more Smart Citation

Solvatochromic and Acid–Base Molecular Probes in Surfactant Micelles: Comparison of Molecular Dynamics Simulation with the Experiment

Mchedlov‐Petrossyan

Farafonov

Lebed

2023

Liquids

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“…The surface interactions can be of various types, such as π-stacking, electrostatic binding, and van der Waals forces . In one such work by Maity et al, it was shown that semicarbazide and thiosemicarbazide pyrene derivatives can interact very differently with anionic and cationic micelles due to the structural factors . The molecules are structurally different due to the CO and CS functional groups, which is sufficient to affect the distribution of π-electrons in the pyrene ring that controlled their hydrophobicity.…”

Section: Importance Of Interfacial Interactionsmentioning

confidence: 99%

“…13 In one such work by Maity et al, it was shown that semicarbazide and thiosemicarbazide pyrene derivatives can interact very differently with anionic and cationic micelles due to the structural factors. 14 The molecules are structurally different due to the C�O and C�S functional groups, which is sufficient to affect the distribution of πelectrons in the pyrene ring that controlled their hydrophobicity. The structural peculiarity modulated the binding of the dyes to the cationic micellar surface and the palisade and Stern layers of the anionic micelles.…”

Section: Importance Of Interfacial Water In the Chemicalmentioning

confidence: 99%

Events at the Interface: How Do Interfaces Modulate the Dynamics and Functionalities of Guest Molecules?

Chatterjee

Purkayastha

2022

Langmuir

Self Cite

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Chemical and biological interfaces are of various types, which could be between two materials of the same and/or different states, two phases of the same material, biological substrates and the outer environment, surfactant or polymeric membranes and the bulk, and so forth. Small-molecule guests frequently interact with such interfaces that decide their functionalities. The structural and behavioral properties undergo considerable characteristic changes, which control their final course of action in the targeted application. This Perspective will discuss mainly the chemical interfaces constituted by the surfactants, polymers, lipids, and nucleic acids and their impacts on the dynamics of small-molecule guests. Some specific and interesting phenomena and future prospects will be elucidated in this Perspective.

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Exploring aggregation‐induced emission through tuning of ligand structure for picomolar detection of pyrene

Ghosh

Lohar³

et al. 2018

J of Molecular Recognition

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Tuning of ligand structures through controlled variation of ring number in fused‐ring aromatic moiety appended to antipyrine allows detection of 7.8 × 10−12 M pyrene via aggregation‐induced emission (AIE) associated with 101‐fold fluorescence enhancement. In one case, antipyrine unit is replaced by pyridine to derive bis‐methylanthracenyl picolyl amine. The structures of four molecules have been confirmed by single crystal X‐ray diffraction analysis. Among them, pyrene‐antipyrine conjugate (L) undergoes pyrene triggered inhibition of photo‐induced electron transfer (PET) leading to water‐assisted AIE.

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Interaction of semicarbazide and thiosemicarbazide pyrene derivatives with anionic and cationic micelles: changed character of pyrene due to alteration in charge density induced by the side chains

Cited by 5 publications

References 26 publications

Solvatochromic and Acid–Base Molecular Probes in Surfactant Micelles: Comparison of Molecular Dynamics Simulation with the Experiment

Solvatochromic and Acid–Base Molecular Probes in Surfactant Micelles: Comparison of Molecular Dynamics Simulation with the Experiment

Events at the Interface: How Do Interfaces Modulate the Dynamics and Functionalities of Guest Molecules?

Exploring aggregation‐induced emission through tuning of ligand structure for picomolar detection of pyrene

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