Designed synthesis of natural rigid dehydroabietylamine-tailored symmetric benzamide organogels by amide bonds and rigid rings coordinated self-assembly strategy

Zhang, Junjie; Gu, Wanting; Xing, Xinwei; Guo, Xuying; Jiang, Jianxin; Song, Jié; Michael, Ryan; Wang, Maogong; Han, Chunrui

doi:10.1016/j.colsurfa.2022.130487

Cited by 8 publications

(11 citation statements)

References 40 publications

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“…The phenol hydroxyl group signal peak appeared in the scope of 3200–3600 cm –1 , announcing that the aliphatic hydroxyl group had a preferential reaction, and the phenol hydroxyl groups remained in the PBDA chain. After chain extension by IPDI, the N–H bending vibration peak of PBDAU can be observed at 1528 cm –1 , which is due to the introduction of the amide structure . The molecular weights of PBA, PBDA, and PBDAU are provided in Figure S1, also indicating the reaction.…”

Section: Resultsmentioning

confidence: 96%

“…After chain extension by IPDI, the N−H bending vibration peak of PBDAU can be observed at 1528 cm −1 , which is due to the introduction of the amide structure. 8 The molecular weights of PBA, PBDA, and PBDAU are provided in Figure S1, also indicating the reaction.…”

Section: Structure Characterizationsmentioning

confidence: 99%

“…This addition of nanoparticles improves the mechanical and barrier performance of the films and also gives it certain antibacterial and ultraviolet (UV) absorption functions. Zhang et al 8 prepared a chitosan-urushiol composite nanofiber membrane by electrospinning. Due to the occurrence of Schiff base reaction between urushiol and chitosan, as well as the self-polymerization of urushiol, the composite membrane had a unique cross-linking structure and multiple antibacterial mechanisms.…”

Section: Introductionmentioning

confidence: 99%

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Degradable Poly(butylene-co-divanillyl adipate) with Intrinsic Free Radical Scavenging and Antibacterial Performance

Yang,

Xiao,

et al. 2023

ACS Appl. Polym. Mater.

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Bioactive polyesters with antibacterial and free radical scavenging functionalities help inhibit the spread of bacteria and eliminate the inflammation, which are of great significance for improving human health. In this study, a bioactive and degradable polyester was designed. First, divanillyl alcohol (DA) was synthesized from vanillin, and the copolymerization of DA, butanediol, adipic acid, and isophorone diisocyanate was conducted to obtain three kinds of polymers: polybutylene adipate (PBA), poly(butylene-co-divanillyl adipate) (PBDA), and chain extended PBDA (named as PBDAU). The H1 NMR and infrared spectra illustrated the successful synthesis of the polymers. Their T g values are −30.5, −31.0, and −28.7 °C, respectively. Interestingly, PBDAU showed intrinsic free radical scavenging activity (RSA). The RSA efficiency of PBDAU can reach up to 100%, while PBDA has 78% and PBA shows no RSA. Furthermore, PBDAU showed inhibition of bacterial growth, especially for the Escherichia coli. The excellent free radical scavenging and antibacterial performance for PBDAU should be associated with the stabilization of phenoxy radicals (Ar–O•), and the easily split-off H•/H+, which will then couple with the free radicals, like “the eagle catches the mouse”. Meanwhile, the polyesters can be degraded under both acidolysis and alkalinolysis conditions. This study is expected to contribute a solution to the synthesis of a bioactive and degradable polyester.

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Section: Resultsmentioning

confidence: 96%

Section: Structure Characterizationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Degradable Poly(butylene-co-divanillyl adipate) with Intrinsic Free Radical Scavenging and Antibacterial Performance

Yang,

Xiao,

et al. 2023

ACS Appl. Polym. Mater.

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“…The observed hydrogen bonding networks involving the amide and other functional groups in the synthesized compounds present exciting prospects for applications in supramolecular chemistry [29] . These intricate networks hold potential implications in diverse fields, particularly in the domains of molecular recognition and the design of organogels through self‐assembly structures [30] . Ongoing investigations in our laboratory are dedicated to exploring this aspect further, focusing on amide species with distinct substitution patterns.…”

Section: Discussionmentioning

confidence: 98%

“…[29] These intricate networks hold potential implications in diverse fields, particularly in the domains of molecular recognition and the design of organogels through self-assembly structures. [30] Ongoing investigations in our laboratory are dedicated to exploring this aspect further, focusing on amide species with distinct substitution patterns.…”

Section: Discussionmentioning

confidence: 99%

Exploring Structural and Spectroscopic Properties of Secondary Amide Derivatives Bearing Bulky and Hydrophilic Substituents

Nossa González,

Gómez Castaño,

Franca

et al. 2023

ChemistrySelect

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The synthesis of four novel amide compounds (R1C(O)NHR2) is reported, which contain both bulky (R1=phenyl and adamantyl) and hydrophilic (R2=hydroxyl, methoxyl) groups. The incorporation of such substituents provides compounds with unique properties that combine steric hindrance and hydrophilicity. The synthesized amides were fully characterized by 1H and 13C nuclear magnetic resonance (NMR) and analysed using infrared (IR) and Raman spectroscopy to investigate their vibrational properties in the solid phase, specifically focusing on the amide‐type normal modes of vibrations. Furthermore, the crystal structures of three derivatives were determined by single‐crystal X‐ray diffraction, which provided insights into their molecular arrangements. The occurrence of N−H⋅⋅⋅O=C hydrogen bonding intermolecular interaction is clearly observed and characterized by Hirschfeld surface analysis. Topology analysis using the Quantum Theory of Atom in Molecules and Crystals (QTAIM−C) were employed to investigate the electronic properties of the isolated amide molecules and to analyse the intermolecular interactions within the crystalline structure. The periodic calculations for the crystal revealed a higher electronic density in the C−N bond, indicating an increased covalent character in this bond compared with the C=O bond. This observation indicates the presence of resonance‐assisted hydrogen bonds within the amide core, leading to π electronic delocalization.

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Molecular design, gel properties, and anti-settling ability with natural rosin-based sulfonamide compounds regulated by conjugation

Guo,

Yao,

Wang

et al. 2024

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Designed synthesis of natural rigid dehydroabietylamine-tailored symmetric benzamide organogels by amide bonds and rigid rings coordinated self-assembly strategy

Cited by 8 publications

References 40 publications

Degradable Poly(butylene-co-divanillyl adipate) with Intrinsic Free Radical Scavenging and Antibacterial Performance

Degradable Poly(butylene-co-divanillyl adipate) with Intrinsic Free Radical Scavenging and Antibacterial Performance

Exploring Structural and Spectroscopic Properties of Secondary Amide Derivatives Bearing Bulky and Hydrophilic Substituents

Molecular design, gel properties, and anti-settling ability with natural rosin-based sulfonamide compounds regulated by conjugation

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