Supramolecular Interaction of Primaquine with Native β-Cyclodextrin

Murugan, Moorthiraman; Anitha, A.; Sivakumar, K.; Rajamohan, R.

doi:10.1007/s10953-018-0768-2

“…To determine stability constants and thermodynamic parameters, a number of techniques are used [6,7], including UV-Vis [8][9][10] and fluorescence [8,9,11] spectroscopy, conductometry [12,13], isothermal calorimetry [14][15][16][17], phase solubility study with UV-Vis spectroscopy [14,18,19] or high-performance liquid chromatography [20], potentiometry [21], capillary electrophoresis [22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39], and other techniques. Capillary electrophoresis (CE) has advantages such as rapidity, high selectivity, a small value of samples, and low-cost of analysis.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic parameters for the complexation of water-soluble betulin derivatives with (2-hydroxypropyl)-β-cyclodextrin determined by affinity capillary electrophoresis

Sursyakova

¹

,

Levdansky

²

,

Rubaylo

³

2019

Journal of Molecular Liquids

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The interaction between (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD) and water-soluble betulin derivatives, betulin 3,28-disulfate (DSB) and betulin 3-acetate-28-sulfate (ASB), belonging to the class of pentacyclic lupane triterpenoids, was studied using affinity capillary electrophoresis. It was found that 1:1 and 1:2 complexes were formed. The stability constants of the complexes in the temperature range of 293.15-318.15 K were determined. The values obtained are sufficiently large; log K (1:1) and log K (1:2) are 4.25-5.02 and 6.08-7.59, respectively. This phenomenon can be explained by the presence of broad hydrophobic regions in the molecules of the compound studied. The stability constants decrease with increasing temperature. The stability constants for ASB complexes are slightly higher as compared to the constants for DSB complexes. The thermodynamic parameters for the complexation were calculated from the van't Hoff plots. The complexation was found to be controlled by the enthalpy change. The obtained values of stability constants at 298 K were compared with values for the β-CD complexes of the compounds under study and for the HP-β-CD an d β-CD complexes of water-insoluble betulin derivatives. It was found that water-soluble betulin derivatives form more stable complexes with CDs as compared to water-insoluble derivatives (betulonic and betulinic acids), and the HP-β-CD complexes are more stable than the β-CD complexes.

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“…Since the three elastomers share the same HMDI and PTMEG2000 components, we ignored those components and synthesized bis‐ethyl isocyanate‐modified DABA (Bis‐EI‐DABA) and bis‐ethyl isocyanate‐modified ADH (Bis‐EI‐ADH) (Figures S16–S21) to investigate how these supramolecular segments amplify the supramolecular effect for a better understanding of the contribution of supramolecular functionalities. Differential scanning calorimetry (DSC) was performed to qualitatively analyze the interactions between the supramolecular segments [38] . The endothermic peak of Bis‐EI‐ADH moved toward a lower temperature with the increase in the Bis‐EI‐DABA content (Figure 2f), indicating that Bis‐EI‐ADH was destabilized by the formation of supramolecular interactions between Bis‐EI‐DABA and Bis‐EI‐ADH.…”

Section: Resultsmentioning

confidence: 99%

“…Differential scanning calorimetry (DSC) was performed to qualitatively analyze the interactions between the supramolecular segments. [38] The endothermic peak of Bis-EI-ADH moved toward a lower temperature with the increase in the Bis-EI-DABA content (Figure 2f), indicating that Bis-EI-ADH was destabilized by the formation of supramolecular interactions between Bis-EI-DABA and Bis-EI-ADH. The density functional theory (DFT) was used to calculate the binding energies of dimers and tetramers comprising rigid (DABA, D) and/or flexible (ADH, A) supramolecular segments.…”

Section: Toughening Effect and Mechanismmentioning

confidence: 98%

Development of Tough Thermoplastic Elastomers by Leveraging Rigid–Flexible Supramolecular Segment Interplays

Wang

¹

,

Guo

²

,

Zhang

³

et al. 2023

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Supramolecular interactions facilitate the development of tough multifunctional thermoplastic elastomers. However, the fundamental principles that govern supramolecular toughening are barely understood, and the rational design to achieve the desired high toughness remains daunting. Herein, we report a simple and robust method for toughening thermoplastic elastomers by rationally tailoring hard–soft phase separation structures containing rigid and flexible supramolecular segments. The introduced functional segments with distinct structural rigidities provide mismatched supramolecular interactions to efficiently tune the energy dissipation and bear an external load. The optimal supramolecular elastomer containing aromatic amide and acylsemicarbazide moieties demonstrates a record toughness (1.2 GJ m−3), extraordinary crack tolerance (fracture energy 282.5 kJ m−2), an ultrahigh true stress at break (2.3 GPa), good elasticity, healing ability, recyclability, and impact resistance. The toughening mechanism is validated by testing various elastomers, confirming the potential for designing and developing super‐tough supramolecular materials with promising applications in aerospace and electronics.

show abstract

Development of Tough Thermoplastic Elastomers by Leveraging Rigid–Flexible Supramolecular Segment Interplays

Wang

¹

,

Guo

²

,

Zhang

³

et al. 2023

View full text Add to dashboard Cite

Supramolecular interactions facilitate the development of tough multifunctional thermoplastic elastomers. However, the fundamental principles that govern supramolecular toughening are barely understood, and the rational design to achieve the desired high toughness remains daunting. Herein, we report a simple and robust method for toughening thermoplastic elastomers by rationally tailoring hard–soft phase separation structures containing rigid and flexible supramolecular segments. The introduced functional segments with distinct structural rigidities provide mismatched supramolecular interactions to efficiently tune the energy dissipation and bear an external load. The optimal supramolecular elastomer containing aromatic amide and acylsemicarbazide moieties demonstrates a record toughness (1.2 GJ m−3), extraordinary crack tolerance (fracture energy 282.5 kJ m−2), an ultrahigh true stress at break (2.3 GPa), good elasticity, healing ability, recyclability, and impact resistance. The toughening mechanism is validated by testing various elastomers, confirming the potential for designing and developing super‐tough supramolecular materials with promising applications in aerospace and electronics.

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Supramolecular Interaction of Primaquine with Native β-Cyclodextrin

Cited by 10 publications

References 30 publications

Thermodynamic parameters for the complexation of water-soluble betulin derivatives with (2-hydroxypropyl)-β-cyclodextrin determined by affinity capillary electrophoresis

Thermodynamic parameters for the complexation of water-soluble betulin derivatives with (2-hydroxypropyl)-β-cyclodextrin determined by affinity capillary electrophoresis

Development of Tough Thermoplastic Elastomers by Leveraging Rigid–Flexible Supramolecular Segment Interplays

Development of Tough Thermoplastic Elastomers by Leveraging Rigid–Flexible Supramolecular Segment Interplays

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