Hydrogen-bonded supercoil self-assembly from achiral molecular components with light-driven supramolecular chirality

Wang, Yangyang; Zhou, Deyan; Li, Haining; Li, Ruiru; Zhong, Yueyao; Sun, Xuan

doi:10.1039/c4tc00649f

Cited by 36 publications

(28 citation statements)

References 47 publications

(23 reference statements)

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“…All of the targeted 4-arylazocinnamic acids were obtained by modified synthetic procedures [14,15,[20][21][22][23][24]. FT-IR, 1 H NMR, and 13 C NMR results of 3A-C correspond to those in the literature [20,23,24].…”

Section: Synthesis Of 4-arylazocinnamic Acidsmentioning

confidence: 85%

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On the azo dyes derived from benzoic and cinnamic acids used as photosensitizersin dye-sensitized solar cells

Matović¹,

Tasić²,

Trišović³

et al. 2019

Turk J Chem

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In order to get a better insight into the relationship between molecular structure and photovoltaic performance, six monoazo dye molecules containing benzoic and cinnamic acid moieties were synthesized and their photovoltaic properties were studied. Three of them have not been previously used in solar cells. Spectroscopic measurements of the investigated compounds coupled with theoretical calculations were performed. Short-circuit current density, open-circuit voltage, and fill-factor were determined. It was found that a larger amount of short-circuit current density will be generated if the HOMO-LUMO energy gap is lower, determined by the stability of the molecule and the electronic effect of the donor moiety. Among both series of synthesized dye molecules, the highest obtained values of short-circuit current density were achieved with (2-hydroxynaphthalene-1-ylazo)benzoic acid and (2-hydroxynaphthalene-1-ylazo)cinnamic acid, and thus they were regarded as promising candidates for application in dye-sensitized solar cells.

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Section: Synthesis Of 4-arylazocinnamic Acidsmentioning

confidence: 85%

“…All azo dyes were obtained by following the synthetic routes presented in Figure 1. Dye molecules derived from benzoic acid were prepared by modified procedures [14,15]. Azo dyes with the cinnamic acid moiety were prepared by a five-step synthetic route.…”

Section: Synthesis Of Dye Moleculesmentioning

confidence: 99%

On the azo dyes derived from benzoic and cinnamic acids used as photosensitizersin dye-sensitized solar cells

Matović¹,

Tasić²,

Trišović³

et al. 2019

Turk J Chem

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“…Apart from a few reports of symmetry breaking in solution [16,38,[56][57][58][59], the introduction of an interface is effective to control the intermolecular interactions, thereby affecting their self-assembly properties. The symmetry also can be broken at a confined two-dimensional (2D) surface/interface during the self-assembly of achiral building blocks [60].…”

Section: Symmetry Breaking In Self-assembly Systemsmentioning

confidence: 99%

Symmetry Breaking in Self-Assembled Nanoassemblies

Sang

Liu

2019

Symmetry

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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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“…Furthermore, the ratio of the two components represents a parameter that can be varied to generate different morphologies and to modulate the properties of the materials . To the best of our knowledge, different kinds of two‐component gels that have been already reported are as follows: carboxylic acids and amines, aromatic donors and acceptors, metal and ligand complex, host and guest complex, organic salts and aromatic substrates, dendrimers and diamines, and so on. Among them, the peptide‐based systems show a unique prospect by virtue of their advantages such as nontoxicity, biodegradability, and biocompatibility .…”

Section: Introductionmentioning

confidence: 99%

Coassembly Modulated pH‐Responsive Hydrogel for Dye Absorption and Release

Wang

Liu

et al. 2017

Macro Chemistry & Physics

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Hydrogel as a carrier for drug delivery system has been developed, but it is hard to change the load and release of drugs through a simple way. Herein, the authors report a novel pH‐sensitive supramolecular binary hydrogel based on Phe‐Gly derivative gelator (LPPG) and 4,4′‐dipyridine disulfide (DPDS). Fourier transform infrared spectroscopy, circular dichroism, and 1H NMR confirm that the driving force for the coassembly process is intermolecular hydrogen bonds. The composite hydrogel can improve the dye adsorption capacity relative to LPPG hydrogel. Moreover, the controllable absorption of the dyes is studied by varying the pH and concentration of dye solutions. LPPG‐DPDS hydrogel can also release of entrapped dyes at physiological pH. The two‐component hydrogel should be a promising system for controllable drug delivery.

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Hydrogen-bonded supercoil self-assembly from achiral molecular components with light-driven supramolecular chirality

Abstract: Supercoils self-assembled from two achiral molecular hydrogen-bonded components have been studied for in-depth understanding of the structure and functionality of this chiral supramolecular association.

Cited by 36 publications

References 47 publications

On the azo dyes derived from benzoic and cinnamic acids used as photosensitizersin dye-sensitized solar cells

On the azo dyes derived from benzoic and cinnamic acids used as photosensitizersin dye-sensitized solar cells

Symmetry Breaking in Self-Assembled Nanoassemblies

Coassembly Modulated pH‐Responsive Hydrogel for Dye Absorption and Release

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