Novel 1,2,3-triazole-based compounds: Iodo effect on their gelation behavior and cation response

Huang, Yuhui; Liu, Shuxue; Xie, Zhuo-Feng; Sun, Zipei; Chai, Wei; Jiang, Wei

doi:10.1007/s11705-017-1683-6

Cited by 12 publications

(6 citation statements)

References 29 publications

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“…Not long after, a new family of 5‐iodo‐1H‐1,2,3‐triazole gelators based on halogen bond interaction have been reported by Huang and co‐workers [47,48] . The iodo gelators (16a, 17a) showed stronger gel properties than the hydrogenous gelators (16b, 17b), which could gel various solvents and formed superorganogels (Scheme 7).…”

Section: Halogen Bonding In Low‐molecular‐weight Gelsmentioning

confidence: 99%

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: Halogen Bonding In Low‐molecular‐weight Gelsmentioning

confidence: 99%

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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“…The same team recently reported how halogenation of phenylalanine in the amyloidogenic sequence DFNKF has a direct effect on the stabilization of the wet interface of the amyloid structures through XB with water molecules, depending on the polarizability of the halogens involved in the interactions, with the iodinated derivatives promoting the most stabilizing interactions . Other authors further proved the efficiency of XB as a gel-forming interaction, using a broad range of organogelators and gelation conditions. − In the quest of building novel smart materials, a photoresponsive two-component supramolecular organogel has recently been reported, whose self-assembly driving force is a synergistic contribution of XB, hydrophobic interactions of long alkyl chains, and π–π interactions (Figure ). The photoresponsive and XB acceptor component is an azopyridine derivative with long alkyl chains to hamper the crystallization process.…”

Section: Supramolecular Gelsmentioning

confidence: 99%

Halogen Bonding beyond Crystals in Materials Science

2019

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Halogen bonding has recently gained well deserved attention in present-day research for its importance in many fields of supramolecular science and crystal engineering. Although generally overlooked in comprehensive studies in the past, halogen bonding has become an important tool also in the field of materials science. An increased number of scientific reports are published every year where halogen bonding is exploited in soft materials rather than in crystal engineering. Here, we focus on a description of the most exciting contemporary developments in the field of halogen-bonded functional soft materials, assembled using the guiding principles of crystal engineering. We give a particular emphasis to those published in the past few years.

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“…Recently, iodine substitution was found to highly improve the gelation properties of various materials. 32 , 33 Despite their importance in many applications, the development of luminous organogelators based on alkoxy-substituted diphenyl ethers has been described in limited studies. 34 , 35 Moreover, the development of fluorescent nanofeather-like organic gelators based on alkoxy-substituted diphenyl ethers has not been reported yet.…”

Section: Introductionmentioning

confidence: 99%

“…Iodo-substituted compounds have been reported as efficient organic gelators, while their corresponding hydrogen-substituted derivatives are not. Recently, iodine substitution was found to highly improve the gelation properties of various materials. , Despite their importance in many applications, the development of luminous organogelators based on alkoxy-substituted diphenyl ethers has been described in limited studies. , Moreover, the development of fluorescent nanofeather-like organic gelators based on alkoxy-substituted diphenyl ethers has not been reported yet. In the current study, organogelators with novel fluorescent alkoxy-substituted diphenyl ethers have been synthesized, characterized, and self-assembled for potential optoelectronic applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Self-assembly of Novel Nanofeather-like Fluorescent Alkyloxy-Containing Diphenyl Ether Organogelators

et al. 2022

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In this study, novel fluorescent low molecular-weight organogelators are derived from diphenyl ethers and substituted with para-alkoxy groups of different aliphatic chain lengths. The present research promotes the preparation of innovative nanofeather-like assemblies from the synthesized diphenyl ether-derived organogelators. The gelation performance of the prepared alkoxy-substituted diphenyl ethers was reported. The synthesis procedure was achieved by using a base-catalyzed reaction of hydroxyl-substituted diphenyl with various alcohols of different aliphatic chain lengths. The chemical structures of the synthesized diphenyl ether derivatives were studied by 1 H/ 13 C NMR and infrared spectroscopy. Fluorescence and UV–vis absorption spectral analyses showed solvatochromism. The diphenyl ether derivatives with longer alkoxy terminal substituents showed enhanced thermoreversible gelation activity as compared to the diphenyl ether derivatives with shorter alkoxy terminal substituents. The morphological properties of the self-assembled diphenyl ethers were studied by transmission electron microscopy and scanning electron microscopy, which showed supramolecular architectures of highly ordered nanofeathers, enforced by van der Waals interactions and π-stacks. Depending on the length of the aliphatic tail, different morphologies were detected, including nanofeathers, nanofibers, and nanosheets. The antimicrobial and cytotoxic properties of the prepared diphenyl ether-derived organogelators were examined to confirm their possible use in various fields like drug delivery systems.

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Novel 1,2,3-triazole-based compounds: Iodo effect on their gelation behavior and cation response

Cited by 12 publications

References 29 publications

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

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

Halogen Bonding beyond Crystals in Materials Science

Synthesis and Self-assembly of Novel Nanofeather-like Fluorescent Alkyloxy-Containing Diphenyl Ether Organogelators

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