Pyran-based derivative: non-conventional organogel and tri-colored high-contrast mechanochromism

Zhang, Jiayu; Lu, Jiayu; Wang, Wen; Zhang, Xinghong; Lan, Haichuang; Xiao, Shuzhang

doi:10.1016/j.tetlet.2022.153888

Cited by 6 publications

(6 citation statements)

References 35 publications

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“…Another interesting approach that the use of electron-deficient heavier halogen substituents (such as iodine in perfluorinated aromatic rings) and good halogen bond acceptor atoms (such as the basic nitrogen of Scheme 20. Chemical structures of halogen bond acceptors (37)(38)(39) and halogen bond donor (DITFB). Reproduced with permission from ref.…”

Section: Discussionmentioning

confidence: 99%

“…Such strategy is conducive to enhancing the luminescence performance of gels and the communication between conjugate units, which realizes the sensing applications with high sensitivity and fast response speed. [37,38,44,45] Recently, halogens have been found to have prominent effects on the construction of low-molecular-weight self-healing gels by cooperating with other non-covalent interactions including π-π stacking, CÀ H…π interaction, H-bonding interaction. The essence of self-healing comes from the re-contact and reassembly of the functional groups produced various non-covalent interactions after mechanical damage.…”

Section: Discussionmentioning

confidence: 99%

“…Similarly, Xiao and co-workers also developed a nonconventional gelator without alkyl chain and amide unit based on a pyran derivative 2b bearing bromine. [38] 1 H NMR, XRD and FT-IR spectra suggested that intermolecular π-π stacking, CN interaction, halogen bonding formation occurred in the gel state. Since similar compound without halogen could only form a partial gel, the introduction of two bromine atoms at the terminal phenyl rings could contribute to enhance intermolecular π-π interactions, resulting in 2b with better self-assembly behaviour.…”

Section: Single-component Halogen Organogelsmentioning

confidence: 97%

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A Review on Low‐Molecular‐Weight Gels Driven by Halogen‐Effect

Zhang

Wang

Liao

et al. 2023

Chemistry An Asian Journal

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As a new type of non-covalent interaction similar to hydrogen bond, halogen bond has become an important supramolecular tool in crystal engineering, material chemistry, biological science, etc., due to its unique properties. In fact, halogen bond has been confirmed on the effect of molecular assemblies and soft materials, and widely used in various functional soft materials including liquid crystals, gels and polymers. In recent years, halogen bonding has aroused strong interest in inducing molecular assembly into low-molecular-weight gels (LMWGs). To the best of our knowledge, there is still a lack of in-depth review of this field. So, in this paper, the recent progress of LMWGs driven by halogen bonding is reviewed. According to the number of components forming halogen bonded gels, the structural characteristics of halogen bonded supramolecular gels, the relationship between halogen bonding and other noncovalent interactions, as well as the application fields of halogen bonded gels are introduced, respectively. In addition, the challenges faced by halogenated supramolecular gels at present and their development prospects in future have been proposed. We believe that the halogen bonded gel will have more impressive applications in the next few years, opening exciting new opportunities for the development of soft materials.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Single-component Halogen Organogelsmentioning

confidence: 97%

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A Review on Low‐Molecular‐Weight Gels Driven by Halogen‐Effect

Zhang

Wang

Liao

et al. 2023

Chemistry An Asian Journal

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“…Journal of Nanomaterials their increased functionality, controllability, and biocompatibility [12][13][14][15][16].…”

Section: Two-dimensional Smart Membrane Advancementmentioning

confidence: 99%

Recent Developments in Stimuli Responsive Smart Materials and Applications: An Overview

Ramakrishnan¹,

Kumar²,

Chelladurai³

et al. 2022

Journal of Nanomaterials

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The term “smart materials” can be used to refer a wide variety of different kinds of substances. One capacity that is shared by all of them is the capability to radically alter one or more aspects while operating inside carefully controlled conditions. The age of intelligent materials is arrived, and we are living in it right now. An older definition of smart material described it as a substance that responds swiftly to the environment in which it is located. It has been argued that the word “smart material” now refers to any substance that is capable of detecting, transmitting, or processing a stimulus in order to produce a beneficial effect. This idea has been put forward as a possible expansion of the original meaning of the term. The purpose of this research is to define and categorize different types of intelligent materials. Uses of smart materials are being contemplated in a wide variety of domains, spanning from the realm of technology to that of the modern environment.

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“…Low-molecular-weight (LMW) gels are a class of soft materials comprising a fibrous network which entraps a solvent [1,2]. The network is formed by LMW gelators, molecules of reduced size, usually lower than 1000 Da, able to self-assemble through non-covalent interactions, such as hydrogen and halogen bonds [3][4][5][6][7], aromatic π-stackings [8,9], and hydrophobic interactions [10,11].…”

Section: Introductionmentioning

confidence: 99%

Transparent Organogels as a Medium for the Light-Induced Conversion from Spiropyran to Merocyanine

Giuri,

Ravarino,

Tomasini

2023

Gels

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Low-molecular-weight peptide gelators are a versatile class of compounds able to form gels under a variety of conditions, even via simple ultrasound sonication. In this paper, the ability of Boc-L-Phe-D-Oxd-L-Phe-OBn to gelate three organic solvents (toluene, tert-butyl methyl ether, and ethanol) was evaluated. The rheological behaviour of the materials was assessed via strain sweep analysis, while the fibrous network was analysed via optical microscopy on the wet gels. The gel obtained from toluene is a highly transparent material, and the one from ethanol appears translucent, while the one from tert-butyl methyl ether is opaque. These gels were used to study the reversible light-induced transformation from spyropiran (SP) to merocyanine (MC) and back, as a model system to check the effect of the gel medium onto the rection kinetic. We observed that the solvent used to form the organogels has a crucial effect on the reaction, as gels from aprotic solvents stabilize the SP form, while the ones from protic solvents stabilize the MC form. We thus obtained a solid support to stabilize the two photochromic species just by changing the solvent polarity. Moreover, we could demonstrate that the self-assembled gels do not interfere with the light-driven conversion process, either starting from SP or MC, thus representing a valid and economical photochromic material.

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Pyran-based derivative: non-conventional organogel and tri-colored high-contrast mechanochromism

Cited by 6 publications

References 35 publications

A Review on Low‐Molecular‐Weight Gels Driven by Halogen‐Effect

A Review on Low‐Molecular‐Weight Gels Driven by Halogen‐Effect

Recent Developments in Stimuli Responsive Smart Materials and Applications: An Overview

Transparent Organogels as a Medium for the Light-Induced Conversion from Spiropyran to Merocyanine

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