Link spacer controlled supramolecular chirality of perylene bisimide-carbohydrate conjugate

RSC Advances ◽  
2015 ◽  
Vol 5 (59) ◽  
pp. 47728-47731 ◽  
Author(s):  
Ke-Rang Wang ◽  
Dan Han ◽  
Guo-Jing Cao ◽  
Xiao-Liu Li
Keyword(s):  
Self Assembly ◽  
The Self ◽  
Amide Bond ◽  
Perylene Bisimide ◽  
Supramolecular Chirality ◽  
Left Handed

Controllable supramolecular chirality based on the self-assembly of the perylene bisimide-carbohydrate conjugates was achieved, exhibiting right-handed chirality with triazole as linker and left-handed chirality with the amide bond as linker.

scholarly journals Insight into the Self-Assembly of Water-Soluble Perylene Bisimide Derivatives Through a Combined Computational and Experimental Approach

2019 ◽  
Author(s):  
Emily R. Draper ◽  
Liam Wilbraham ◽  
Dave J. Adams ◽  
Matthew Wallace ◽  
Martijn Zwijnenburg
Keyword(s):  
Density Functional Theory ◽  
Self Assembly ◽  
Density Functional ◽  
Colloidal Stability ◽  
Water Soluble ◽  
The Self ◽  
Functional Theory ◽  
Perylene Bisimide ◽  
Aggregate Growth ◽  
Perylene Bisimides

We use a combination of computational and experimental techniques to study the self-assembly and gelation of water-soluble perylene bisimides derivatised at the imide position with an amino acid. Specifically, we study the likely structure of self-assembled aggregates of the alanine-functionalised perylene bisimide (PBI-A) and the thermodynamics of their formation using density functional theory and predict the UV-vis spectra of such aggregates using time-dependent density functional theory. We compare these predictions to experiments in which we study the evolution of the UV-Vis and NMR spectra and rheology of alkaline PBI-A solutions when gradually decreasing the pH. Based on the combined computational and experimental results, we show that PBI-A self-assembles at all pH values but that aggregates grow in size upon protonation. Gelation is driven not by aggregate growth but reduction of the aggregation surface-charge and a decrease in the colloidal stability of the aggregation with respect to agglomeration.

scholarly journals Insight into the self-assembly of water-soluble perylene bisimide derivatives through a combined computational and experimental approach

Nanoscale ◽  
2019 ◽  
Vol 11 (34) ◽  
pp. 15917-15928 ◽  
Author(s):  
Emily R. Draper ◽  
Liam Wilbraham ◽  
Dave J. Adams ◽  
Matthew Wallace ◽  
Ralf Schweins ◽  
...  
Keyword(s):  
Amino Acid ◽  
Self Assembly ◽  
Experimental Approach ◽  
Water Soluble ◽  
The Self ◽  
Experimental Techniques ◽  
Perylene Bisimide ◽  
Perylene Bisimides ◽  
Insight Into

We use a combination of computational and experimental techniques to study the self-assembly and gelation of amino-acid functionalised water-soluble perylene bisimides.

scholarly journals Tunable Supramolecular Chirogenesis in the Self-Assembling of Amphiphilic Porphyrin Triggered by Chiral Amines

2020 ◽  
Vol 21 (22) ◽  
pp. 8557
Author(s):  
Marco Savioli ◽  
Manuela Stefanelli ◽  
Gabriele Magna ◽  
Francesca Zurlo ◽  
Maria Federica Caso ◽  
...  
Keyword(s):  
Self Assembly ◽  
Hydrophobic Effect ◽  
The Self ◽  
Chiral Amines ◽  
Solvent Mixtures ◽  
Fractal Structures ◽  
Chiral Amine ◽  
Supramolecular Chirality ◽  
Self Assembling ◽  
Aqueous Solvent

Supramolecular chirality is one of the most important issues in different branches of science and technology, as stereoselective molecular recognition, catalysis, and sensors. In this paper, we report on the self-assembly of amphiphilic porphyrin derivatives possessing a chiral information on the periphery of the macrocycle (i.e., D- or L-proline moieties), in the presence of chiral amines as co-solute, such as chiral benzylamine derivatives. The aggregation process, steered by hydrophobic effect, has been studied in aqueous solvent mixtures by combined spectroscopic and topographic techniques. The results obtained pointed out a dramatic effect of these ligands on the morphology and on the supramolecular chirality of the final self-assembled structures. Scanning electron microscopy topography, as well as fluorescence microscopy studies revealed the formation of rod-like structures of micrometric size, different from the fractal structures formerly observed when the self-assembly process is carried out in the absence of chiral amine co-solutes. On the other hand, comparative experiments with an achiral porphyrin analogue strongly suggested that the presence of the prolinate moiety is mandatory for the achievement of the observed highly organized suprastructures. The results obtained would be of importance for unraveling the intimate mechanisms operating in the selection of the homochirality, and for the preparation of sensitive materials for the detection of chiral analytes, with tunable stereoselectivity and morphology.

scholarly journals pH dependent photocatalytic hydrogen evolution by self-assembled perylene bisimides

2017 ◽  
Vol 5 (16) ◽  
pp. 7555-7563 ◽  
Author(s):  
Michael C. Nolan ◽  
James J. Walsh ◽  
Laura L. E. Mears ◽  
Emily R. Draper ◽  
Matthew Wallace ◽  
...  
Keyword(s):  
Photocatalytic Activity ◽  
Hydrogen Evolution ◽  
Self Assembly ◽  
The Self ◽  
Photocatalytic Hydrogen Evolution ◽  
Perylene Bisimide ◽  
Ph Dependent ◽  
Self Assembled ◽  
Perylene Bisimides

We show the importance of the self-assembly of a perylene bisimide on its photocatalytic activity.

scholarly journals Insight into the Self-Assembly of Water-Soluble Perylene Bisimide Derivatives Through a Combined Computational and Experimental Approach

2019 ◽  
Author(s):  
Emily R. Draper ◽  
Liam Wilbraham ◽  
Dave J. Adams ◽  
Matthew Wallace ◽  
Martijn Zwijnenburg
Keyword(s):  
Density Functional Theory ◽  
Self Assembly ◽  
Density Functional ◽  
Colloidal Stability ◽  
Water Soluble ◽  
The Self ◽  
Functional Theory ◽  
Perylene Bisimide ◽  
Aggregate Growth ◽  
Perylene Bisimides

We use a combination of computational and experimental techniques to study the self-assembly and gelation of water-soluble perylene bisimides derivatised at the imide position with an amino acid. Specifically, we study the likely structure of self-assembled aggregates of the alanine-functionalised perylene bisimide (PBI-A) and the thermodynamics of their formation using density functional theory and predict the UV-vis spectra of such aggregates using time-dependent density functional theory. We compare these predictions to experiments in which we study the evolution of the UV-Vis and NMR spectra and rheology of alkaline PBI-A solutions when gradually decreasing the pH. Based on the combined computational and experimental results, we show that PBI-A self-assembles at all pH values but that aggregates grow in size upon protonation. Gelation is driven not by aggregate growth but reduction of the aggregation surface-charge and a decrease in the colloidal stability of the aggregation with respect to agglomeration.

The effect of amide bond orientation and symmetry on the self-assembly and gelation of discotic tripeptides

Soft Matter ◽  
2021 ◽  
Vol 17 (1) ◽  
pp. 113-119
Author(s):  
Santosh Kumar ◽  
Santu Bera ◽  
Sujay Kumar Nandi ◽  
Debasish Haldar
Keyword(s):  
Self Assembly ◽  
The Self ◽  
Amide Bond

The C3-symmetric N-centered and CO-centered discotic tripeptides form 3-fold intermolecular H-bonded helical column and organogels, whereas the C2-symmetric discotic tripeptides adopt 6-fold intermolecular H-bonded dimer and microspheres structures.

The formation of right-handed and left-handed chiral nanopores within a single domain during amino acid self-assembly on Au(111)

2016 ◽  
Vol 18 (21) ◽  
pp. 14172-14176
Author(s):  
Sena Yang ◽  
Aram Jeon ◽  
Russell W. Driver ◽  
Yeonwoo Kim ◽  
Eun Hee Jeon ◽  
...  
Keyword(s):  
Amino Acid ◽  
Acid Derivative ◽  
Self Assembly ◽  
The Self ◽  
Single Domain ◽  
Amino Acid Derivative ◽  
Left Handed

We report the formation of both right- and left-handed chiral nanopores within a single domain during the self-assembly of an amino acid derivative on an inert Au(111) surface using STM.

Left-Handed Helical Ribbon Intermediates in the Self-Assembly of a β-Sheet Peptide

Nano Letters ◽  
2002 ◽  
Vol 2 (4) ◽  
pp. 295-299 ◽  
Author(s):  
Davide M. Marini ◽  
Wonmuk Hwang ◽  
Douglas A. Lauffenburger ◽  
Shuguang Zhang ◽  
Roger D. Kamm
Keyword(s):  
Self Assembly ◽  
The Self ◽  
Helical Ribbon ◽  
Left Handed ◽  
Β Sheet

scholarly journals Symmetry Breaking in Self-Assembled Nanoassemblies

Symmetry ◽  
2019 ◽  
Vol 11 (8) ◽  
pp. 950 ◽  
Author(s):  
Yutao Sang ◽  
Minghua Liu
Keyword(s):  
Symmetry Breaking ◽  
Self Assembly ◽  
Mirror Symmetry ◽  
Covalent Bond ◽  
The Self ◽  
Control Methods ◽  
Supramolecular Chirality ◽  
Dispersed System ◽  
Chiral Materials ◽  
And Control

The origin of biological homochirality, e.g., life selects the L-amino acids and D-sugar as molecular component, still remains a big mystery. It is suggested that mirror symmetry breaking plays an important role. Recent researches show that symmetry breaking can also occur at a supramolecular level, where the non-covalent bond was crucial. In these systems, equal or unequal amount of the enantiomeric nanoassemblies could be formed from achiral molecules. In this paper, we presented a brief overview regarding the symmetry breaking from dispersed system to gels, solids, and at interfaces. Then we discuss the rational manipulation of supramolecular chirality on how to induce and control the homochirality in the self-assembly system. Those physical control methods, such as Viedma ripening, hydrodynamic macro- and micro-vortex, superchiral light, and the combination of these technologies, are specifically discussed. It is hoped that the symmetry breaking at a supramolecular level could provide useful insights into the understanding of natural homochirality and further designing as well as controlling of functional chiral materials.

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