Robust scalable synthesis of a bis-urea derivative forming thixotropic and cytocompatible supramolecular hydrogels

Rutgeerts, Laurens A. J.; Al‐Halifa, Soultan; Subramani, Ramesh; Toprakhisar, Burak; Ramón, Herman; Paderes, Monissa C.; Borggraeve, Wim M. De; Patterson, Jennifer

doi:10.1039/c9cc02927c

Cited by 27 publications

(32 citation statements)

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“…Starting from the recently reported hydrogelator P1m1, a library of derivatives was synthesized (Table 1). [8] Both the substitution pattern of the pyridine rings as well as the number of methylene units was systematically modified, resulting in 12 new compounds. All compounds were synthesized using wellestablished amino-isocyanate chemistry.…”

Section: Synthesis Of Compound Library and Assessment Of Hydrogelatiomentioning

confidence: 99%

“…Since then, the number of urea‐based LMWGs capable of gelling organic solvents (organogelators) increased significantly, but there are still few urea‐based gelators known to gel water (hydrogelators) . Very recently, our group reported the discovery of an inexpensive cytocompatible bis‐urea based low molecular weight hydrogelator (LMWH), P1 m 1 (Figure ) . The robust and accessible synthetic route to P1 m 1 makes derivatization towards novel LMWHs straightforward.…”

Section: Introductionmentioning

confidence: 99%

“…Herein, this technique showcases its ability to visualise and characterize the different non‐covalent interactions involved in the self‐assembly leading to gelation. The bottom‐up approach was carried out on a set of twelve newly synthesized compounds derived from the recently reported hydrogelator, P1 m 1 …”

Section: Introductionmentioning

confidence: 99%

“…[3,6,7] Very recently, our group reported the discovery of an inexpensive cytocompatible bis-urea based low molecular weight hydrogelator (LMWH), P1m1 (Figure 1). [8] The robust and accessible synthetic route to P1m1 makes derivatization towards novel LMWHs straightforward.…”

Section: Introductionmentioning

confidence: 99%

“…The bottomup approach was carried out on a set of twelve newly synthesized compounds derived from the recently reported hydrogelator, P1m1. [8]…”

Section: Introductionmentioning

confidence: 99%

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Rationalising Supramolecular Hydrogelation of Bis‐Urea‐Based Gelators through a Multiscale Approach

et al. 2019

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The current approach to designing low‐molecular‐weight gelators relies on a laborious trial‐and‐error process, mainly because of the lack of an accurate description of the noncovalent interactions crucial for supramolecular gelation. In this work, we report a multiscale bottom‐up approach composed of several computational techniques to unravel the key interactions in a library of synthesized bis‐urea‐based gelators and rationalize their experimentally observed hydrogelation performance. In addition to density functional theory calculations and molecular dynamics, the noncovalent interaction index is applied as a tool to visualise and identify the different types of noncovalent interactions. Interestingly, as well as hydrogen bonds between urea moieties, hydrogen bonds between a urea moiety and a pyridine ring were shown to play a detrimental role in the early aggregation phase. These findings enabled us to explain the hydrogelation performance observed in a library of twelve bis‐urea derivatives, which were synthesized with 58–95 % yields. From this library, three compounds were discovered to effectively gel water, with the most efficient hydrogelator only requiring a concentration of 0.2 w/v%.

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Section: Synthesis Of Compound Library and Assessment Of Hydrogelatiomentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…The bottomup approach was carried out on a set of twelve newly synthesized compounds derived from the recently reported hydrogelator, P1m1. [8]…”

Section: Introductionmentioning

confidence: 99%

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Rationalising Supramolecular Hydrogelation of Bis‐Urea‐Based Gelators through a Multiscale Approach

et al. 2019

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Hydrogel Nanocomposite Adsorbents and Photocatalysts for Sustainable Water Purification

Kumar

Gusain

Pandey

et al. 2022

Adv Materials Inter

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Anthropogenic actions, environmental catastrophes, urbanization, population growth, and industrialization generate toxic pollutants in water bodies. The most pollutants are heavy metals and metalloids, dyes, volatile organic compounds, pharmaceuticals, pesticides, radionuclides, aromatic hydrocarbons, oils, polycyclic aromatic hydrocarbons, microbes/pathogens, and microplastics that can be in different forms and concentrations. [3][4][5] Globally, approximately 2 million tons of pollutants from agriculture, industrial, and sewage waste are released into water streams, which pose severe health risks and cause the deaths of more than 1400 people every day. [6] Thus, developing efficient, economical, environmentalfriendly, and scalable technologies for the purification of wastewater and seawater is urgently required. To fulfill the shortage of clean water, affordable technologies can be used to transform unconventional water reserves (such as wastewater, rainfall, seawater, and brackish water) into potable water. Recently, numerous water treatment technologies, including coagulation/flocculation, filtration, chemical precipitation, aerobic/anaerobic processing, biological treatment, electrochemically precipitation, advanced oxidation processing, membrane separation, ion-exchange, adsorption, solar/thermal distillation/evaporation, crystallization, and photocatalysis, have emerged to offer practical solutions to water pollution management. [7][8][9][10][11][12][13][14] Among them, adsorption and photocatalysis technologies have garnered significant attention from the research community due to their cost-effectiveness, high performance, Hydrogels have been employed for water purification applications, but their performance and strength are unsatisfactory for widespread adoption. Recently, hydrogel nanocomposites have been proposed to resolve the inherent challenges faced by hydrogels for water treatment. This review comprehensively analyzes hydrogel nanocomposites for water treatment using adsorbent and photocatalysis techniques. The structure, classification, and tunable synthesis methods of hydrogels are explained. Further, how hydrogels can be incorporated with functional nanoparticles (NPs) and can be used as templates/precursors for developing advanced 3D architectures, including the formation of hydrogel nanocomposite beads and 3D printing objects are discussed. Finally, the structure-property relationships of hydrogel nanocomposites are critically reviewed by considering introductory gelation chemistry, such as swelling characteristics, mechanical properties, stimuli-responsiveness, and ionic/electronic conduction. The extensive cross-linking of polymer chains with NPs offers high mass/charge transport, high surface areas, and enhanced polymer-water interactions to achieve high-performing adsorbents and photocatalysts. Several motivating examples of emerging NP-containing hydrogel nanocomposites for use in adsorbents and photocatalysis have been discussed. Such efforts validated the excellent technological pote...

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Urea Derivatives as Functional Molecules: Supramolecular Capsules, Supramolecular Polymers, Supramolecular Gels, Artificial Hosts, and Catalysts

Yokoya

Kimura

Yamanaka

2021

Chemistry A European J

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Urea, which has both hydrogen bond acceptor and donor moieties, is an ideal structuref or as upramolecular synthon. Various supramolecules having ureido group(s) have been widelyd eveloped. This article summarizes recent developments of urea derivatives that exhibit various functions:i)supramolecular capsules that form discreteu reaurea intermolecular hydrogen bonds, ii)supramolecular polymers that form continuous urea-urea intermolecularh ydrogen bonds, iii)supramolecular gels that form continuous urea-urea intermolecular hydrogen bonds, iv) artificialh ost molecules based on the molecular recognition ability of the ureido group, and v) catalytic reactions developedb yu tilizing the molecular recognition ability of the ureido group.

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Robust scalable synthesis of a bis-urea derivative forming thixotropic and cytocompatible supramolecular hydrogels

Abstract: Cytocompatible nanofibrous thixotropic supramolecular hydrogel based on a low molecular weight bis-urea derivative.

Cited by 27 publications

References 31 publications

Rationalising Supramolecular Hydrogelation of Bis‐Urea‐Based Gelators through a Multiscale Approach

Rationalising Supramolecular Hydrogelation of Bis‐Urea‐Based Gelators through a Multiscale Approach

Hydrogel Nanocomposite Adsorbents and Photocatalysts for Sustainable Water Purification

Urea Derivatives as Functional Molecules: Supramolecular Capsules, Supramolecular Polymers, Supramolecular Gels, Artificial Hosts, and Catalysts

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