Solvation Effects in Supramolecular Chemistry

Kanagaraj, Kuppusamy; Alagesan, Mani; Inoue, Yoshihisa; Yang, Cheng

doi:10.1016/b978-0-12-409547-2.12481-3

Cited by 13 publications

(6 citation statements)

References 307 publications

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“…While numerous lifesaving drugs have successfully been elaborated following this strategy over the past century, the reports of highly efficient artificial hosts targeting biomolecules are more seldom 2. Indeed, the design of synthetic hosts working in highly dissociative aqueous media requires not only the anticipation of the nature and strength of the non-covalent interactions with the target guest molecules, but also grasping the crucial role of the multiple water molecules surrounding the binding partners during the process 3. In the past few years, cucurbiturils have joined the restricted circle of cavitands, such as cyclodextrins and functionalized cyclophanes, successfully operating in water 2 a .…”

Section: Introductionmentioning

confidence: 99%

Wetting the lock and key enthalpically favours polyelectrolyte binding

et al. 2019

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Section: Introductionmentioning

confidence: 99%

Wetting the lock and key enthalpically favours polyelectrolyte binding

et al. 2019

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“…Although this may be surprising at first, these results can be attributed to the fact that for these oligomeric structures to be formed in solution, free monomers, which are also solvated, must undergo desolvation to proceed with the oligomerization. [43,44] This explains the trend reversal in the aqueous formation energies of the cyclic dipeptides. Since the diketopiperazine ring pore structure utilizes all four hydrogen bonding sites (Figure 1B) for oligomerization, this would translate to a larger energy requirement in desolvating these sites of the monomer.…”

Section: Free Energies Of Formation and Solvationmentioning

confidence: 82%

Stackable Aromatic Dipeptide Ring Structures toward Nanotube Formation: Thermodynamics and Interactions in Gas‐Phase and Solution

Visayas

Mayes

2021

ChemistrySelect

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Increasing attention has been drawn towards self‐assembling dipeptide nanotube materials (NT) for their tunable properties. Despite recent advances, a fundamental understanding of the conditions that drive the self‐assembly process is still lacking. Here, we report the structures, thermodynamics, and underlying interactions of the nanotube forming potential of cyclic and linear aromatic dipeptides phenylalanine‐tyrosine, tryptophan‐tyrosine, and dityrosine via the piecewise self‐assembly mechanism. The cyclic dipeptides have better favorability of oligomerization in the gas phase than the linear dipeptides, largely due to the enthalpic gain of forming more hydrogen bonds, suggesting that the piecewise mechanism is plausible for vapor deposition methods. Oligomerization in solution, which would require desolvation of free monomers, was shown to be thermodynamically unfavorable, especially in polar solvents, demonstrating the need for an external stimulus for the crystallization of NTs. The generated oligomeric rings show structural robustness and symmetry, allowing excellent stacking potential in both lateral and axial directions. The nature of the sidechains significantly affects the stabilizations within the oligomeric structure. The insights generated can be used as a basis for dipeptide modifications that could enhance targeted NT properties for different applications.

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“…ΔS o , where R and T correspond to the ideal gas constant and temperature, respectively. Solvents are capable of influencing the abovedescribed equilibrium by affecting the terms ΔH ο and ΔS o [9,10]. When it comes to Supramolecular Complexation (SC), a general classification of solvents is based on their aptitude to undertake to self-organization.…”

Section: Supramolecular Recognition 21 General Aspectsmentioning

confidence: 99%

Solvent Effects in Supramolecular Systems

Papadakis¹,

Deligkiozi²

2020

Solvents, Ionic Liquids and Solvent Effects

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Today it is well-established that solvents demonstrate an important role in chemistry. Solvents are able to affect the reactivity, as well as the electronic, optical, and generally physicochemical properties of compounds in solution. Taking this into account, in this chapter we analyze the importance of solvent polarity in phenomena closely related to supramolecular systems as well as the aptitude of various supramolecules to interact with solvent molecules and thus to give rise to chromic effects such as solvatochromism. Main focus is placed on mechanically interlocked molecules, e.g., rotaxanes, catenanes, etc., exhibiting solvent-controlled shuttling movements, switching, and/or solvatochromism. The effect of solvents in various supramolecular architectures is a further focus of this chapter.

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Solvation Effects in Supramolecular Chemistry

Cited by 13 publications

References 307 publications

Wetting the lock and key enthalpically favours polyelectrolyte binding

Wetting the lock and key enthalpically favours polyelectrolyte binding

Stackable Aromatic Dipeptide Ring Structures toward Nanotube Formation: Thermodynamics and Interactions in Gas‐Phase and Solution

Solvent Effects in Supramolecular Systems

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