Chirality controlled responsive self-assembled nanotubes in water

Dijken, Derk Jan van; Štacko, Peter; Stuart, Marc C. A.; Browne, Wesley R.

doi:10.1039/c6sc02935c

Cited by 23 publications

(23 citation statements)

References 55 publications

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“…1). In the practice of pharmaceutical analysis of substances, it is not possible to identify a violation of Biot's Law, since pharmacopoeia methods of polarimetric quality control involve the use of more concentrated solutions (2-10%) [13][14][15]. Thus, the observed violation of the Biot law is explained by the instability of optically active AA in DMF.…”

Section: Resultsmentioning

confidence: 99%

Ascorbiс Acid Degradation in N, N-Dimethylformamide Solutions

et al. 2020

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Objective: Investigate the mechanisms of L-ascorbic acid transforтmation and formation of coloured enamines in N, N-dimethyl-formamide solutions. Methods: An automatic polarimeter Atago POL-1/2 was used for polarimetric investigation. Electronic spectra were recorded by UV-spectrometer Cary 60 (Agilent). The statistical analysis was carried out using the OriginPro 9.1 packages. Results: The Biot’s law violation was found in below 0.1% solutions of L-ascorbic acid (AA) in N, N-dimethylformamide (DMF). During the day, the specific rotation of 1% AA solution varied from+37 to-1.0. Gradually, the solution acquired the red colour, and its intensity depended on the AA concentration. Spectrophotometrically, it was shown that after 15 min AA was absent in the n·10-3% solutions. The decomposition followed the first-order kinetics (k1=1.83·10-2с-1). At the same time, new absorption bands appeared at 273, 390, 533 nm. Model solutions containing dimethylamine (DMA) had a similar spectrum, and the intensity of the absorption bands increased in proportion to the concentration of DMA. Conclusion: The results show that the first step in the decomposition of ascorbic acid AA in DMF follows first-order kinetics. Numerous decomposition products are optically active compounds and reverse the sign of the optical rotation of the solution. The water resulting from the decomposition of AA is involved in the hydrolysis of the solvent. The hydrolysis product, the secondary amine DMA, interacts with the carbonyl groups of the AA decomposition products to form coloured enamines. Magnesium (II) accelerates the formation of coloured products.

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Section: Resultsmentioning

confidence: 99%

Ascorbiс Acid Degradation in N, N-Dimethylformamide Solutions

et al. 2020

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“…Helical materials with chirality have been a subject of an intensive research for their applications ranging from nano‐ and microreaction vessels and targeted drug delivery. Usually, helicity and chirality are expressed as responsive signal and can be analyzed under circular polarized light . Block copolymers reported here were characterized by CD for their optical properties with regard to the formation of helix via poly(phenyl isocyanide) segment.…”

Section: Resultsmentioning

confidence: 99%

Self‐Assembly and Responsive Behavior of Poly(peptide)‐Based Copolymers

Kumar

Hertel

Müllen

2018

Macro Chemistry & Physics

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Well‐defined copolymers synthesized by combining poly(ethylene glycol) (PEG) and amino acid based building blocks are investigated with regard to their helical rigidity and self‐assembly. Optical active block copolymers reported here are designed to have a pendant amino acid and polymerizable group, that is, isonitrile in order to induce helix formation and reduce the mobility of polymer chains by forming a hydrogen bond network so that a helix with reasonable rigidity can be obtained. Due to the amphiphilicity and a relatively shorter PEG as a coil, these polymers form micelles as observed under transmission electron microscopy in which copolymers PEG108‐b‐PPIC764 and PEG108‐b‐PPIC1020 appear to be evolving into nanoparticles with a size distribution of 100–200 nm. Circular dichroism spectroscopy is employed to study the nature of the helix and its rigidity. The folding and unfolding of polymer helix as a result of the ability of a selective solvent to form/disrupt hydrogen bonds with the peptide linkage is also discussed to highlight the responsive nature of the polymer.

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“…Van Dijken et al [ 53 ] have reported the synthesis of enantiomerically pure supercoiled helical NTs in water simply doping the achiral tubular structure of amphiphile 15a with small amounts of a closely related enantiopure analogue 15b . Only small amounts of enantiomerically pure compound is required to control CD-response and, more importantly, the morphology of the chiral NTs ( Figure 12 ).…”

Section: Discussionmentioning

confidence: 99%

Chiral Nanotubes

2017

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Organic nanotubes, as assembled nanospaces, in which to carry out host–guest chemistry, reversible binding of smaller species for transport, sensing, storage or chemical transformation purposes, are currently attracting substantial interest, both as biological ion channel mimics, or for addressing tailored material properties. Nature’s materials and machinery are universally asymmetric, and, for chemical entities, controlled asymmetry comes from chirality. Together with carbon nanotubes, conformationally stable molecular building blocks and macrocycles have been used for the realization of organic nanotubes, by means of their assembly in the third dimension. In both cases, chiral properties have started to be fully exploited to date. In this paper, we review recent exciting developments in the synthesis and assembly of chiral nanotubes, and of their functional properties. This review will include examples of either molecule-based or macrocycle-based systems, and will try and rationalize the supramolecular interactions at play for the three-dimensional (3D) assembly of the nanoscale architectures.

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Chirality controlled responsive self-assembled nanotubes in water

Abstract: We report the design, synthesis and study of nanotube-forming light-responsive amphiphiles, in which chirality can be used as a means to control the morphologies of self-assembled structures.

Cited by 23 publications

References 55 publications

Ascorbiс Acid Degradation in N, N-Dimethylformamide Solutions

Ascorbiс Acid Degradation in N, N-Dimethylformamide Solutions

Self‐Assembly and Responsive Behavior of Poly(peptide)‐Based Copolymers

Chiral Nanotubes

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