Amphiphilic oligoamides as versatile, acid-responsive gelators

Pei, Qiang; Tang, Quan; Tan, Zheng-Li; Lu, Zhong‐Lin; Gong, Bing

doi:10.1039/c7ra03074f

Cited by 5 publications

(5 citation statements)

References 39 publications

(21 reference statements)

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“…The three-dimensional (3-D) network-like morphology of these xerogels was observed under a scanning electron microscope (SEM). − The xerogel of MCH appeared as a 3-D cross-linked network-like cage structure, and toluene xerogel came out as regularly arranged 3-D clusters (Figure S10).…”

Section: Results and Discussionmentioning

confidence: 99%

Organogels Fabricated from Self-Assembled Nanotubes Containing Core Substituted Perylene Diimide Derivative

Moharana

Santosh

2022

ACS Omega

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Perylene-based organogels are well-known for their applications as sensors and optoelectronic materials. Among them, core-substituted perylene diimide-based organogels are rarely explored. Herein, the hierarchical self-assembly mechanism of a newly synthesized, amide-linked core-substituted perylene diimide derivative, which formed organogels in organic solvents like toluene and methyl cyclohexane (MCH), is discussed. These organogels are composed of one-dimensional molecular aggregates like nanofibers and nanotubes. Organogels composed of nanofibers are very frequent. On the contrary, for the first time, we have encountered a perylene diimide-based organogel consisting of self-assembled nanotubes. The molecular interactions, molecular packing, and rheological properties of this organogel are also discussed.

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Section: Results and Discussionmentioning

confidence: 99%

Organogels Fabricated from Self-Assembled Nanotubes Containing Core Substituted Perylene Diimide Derivative

Moharana

Santosh

2022

ACS Omega

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“…Typical nanostructures and microstructures, such as fibers, tubes, ribbons, and films, can form during the gelation of LMWGs [44] . The morphology of GSSN and GN gels was studied using SEM (Figure 7).…”

Section: Resultsmentioning

confidence: 99%

“…Typical nanostructures and microstructures, such as fibers, tubes, ribbons, and films, can form during the gelation of LMWGs. [44] The morphology of GSSN and GN gels was studied using SEM (Figure 7). Xerogels of GSSN obtained from EtOAc and DMSO and GN obtained from EtOAc, MeOH, and acetone presented entangled fibers with different size distributions (100 ∼ 200 nm in diameter).…”

Section: Sem Studymentioning

confidence: 99%

Gallic‐Acid‐Modified Naphthalimide Containing Disulfide Bond as Reduction‐Responsive Supramolecular Organogelator

et al. 2022

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The development of low molecular‐weight gelators for the construction of stimuli‐responsive gels is increasing attention because of the great application potential. In this work, we report the design and synthesis of two new naphthalimide derivatives, GSSN and GN, as supramolecular organogelators. GSSN contains a disulfide bond in the molecule, while GN contains no disulfide bond. As a result, only GSSN exhibited reduction responsiveness. A series of tests, including UV‐vis, temperature‐dependent 1H NMR, XRD, and SEM, were carried out to characterize the gelation capability and probe into the gelation mechanism. Results showed that GN can gelate more organic solvents than GSSN. Both hydrogen bonding and π stacking contribute to the gelation. Due to the difference in the assembly of the organogelator molecules, the organogels formed by GSSN and GN presented distinct morphologies. Moreover, strong hydrophobicity was found in the organogel films of GSSN and GN, suggesting potential application as hydrophobic coating materials.

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“…具有直线型拓展结构的分子, 可以通过分子间的非共价作用力边对边地聚集形成分子拉链 [80][81] . 袁立华等 [82][83] 用酰亚胺或脲基为连接单元, 合成了一系列具有不同的多重氢键结合位点的分子链.…”

Section: 线性拓展化合物unclassified

Supramolecular Assemblies Based on Intramolecular Three-Center Hydrogen Bond and their Applications

Pei¹,

Ding²,

Wu³

2021

Chinese Journal of Organic Chemistry

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The intramolecular three-center hydrogen bond is regarded as an efficient and reliable means to control molecular conformation, which can induce linear molecules to form specific conformations (folding, helix, expansion, zigzag, etc.). In this paper, the research progress on supramolecular assemblies based on different types of intramolecular three-center hydrogen bond is summarized in detail according to the kinds of hydrogen bonding atoms, such as O…H…O, S…H…X (X＝ N, O), N…H…X (X＝N, O), F…H…X (X＝F, O, N), and so on. More specifically, the synthesis of supramolecular assemblies is elaborated, including macrocyclic compounds, foldamers, porous helical compounds and molecular duplexes. Furthermore, their applications in promoting organic reactions, molecular recognition, transmembrane channels, molecular machines, soft materials are introduced. It is anticipated that this review can provide a useful reference for the synthesis and applications of the three-center hydrogel bond-based supramolecular assemblies. Keywords intramolecular three-center hydrogen bond; supramolecular self-assembly; structure design; conformation control; application [1] . 氢键强度适中, 具有方向性、饱和性以及动态可逆性, 是自然界中最基本的分子间弱相互作用力之一, 被广泛应用于超分子自组装领域 [2] . 此外, 氢键的结合方式丰富 [3][4] . 根据组成氢键的氢键给体和氢键受体数目之和, 可以分为两中心氢键 (1)、三中心氢键(2 和 3)以及四中心氢键(4)等(图 1). 其中, 三中心氢键最初被称为"分叉型"(Bifurcated)氢键, 存在 2 种不同形式, 即 XHY 型(H 为氢键给体, X/Y 为氢键受体, 2)和 HXH 型(H 为氢键给体, X 为氢键受体, 3). 后来, Maluszynska [5] 和 Taylor 等 [6] 建议将 XHY 型氢键称作三中心氢键. 事实上, 早在 1939 年 Albrecht 等 [7] 就发现在 α-氨基乙酸晶体中存在上述定义的氢键. 直到 20 世纪 80 年代, 因在更多小分子和生物大分子的固态结构中发现这种氢键, 人们才逐渐接受和重视三中心氢键概念 [8] .

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Amphiphilic oligoamides as versatile, acid-responsive gelators

Cited by 5 publications

References 39 publications

Organogels Fabricated from Self-Assembled Nanotubes Containing Core Substituted Perylene Diimide Derivative

Organogels Fabricated from Self-Assembled Nanotubes Containing Core Substituted Perylene Diimide Derivative

Gallic‐Acid‐Modified Naphthalimide Containing Disulfide Bond as Reduction‐Responsive Supramolecular Organogelator

Supramolecular Assemblies Based on Intramolecular Three-Center Hydrogen Bond and their Applications

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