A family of simple benzene 1,3,5-tricarboxamide (BTA) aromatic carboxylic acid hydrogels

Howe, Richard C. T.; Smalley, Adam P.; Guttenplan, Alexander P. M.; Doggett, Matthew W. R.; Eddleston, Mark D.; Tan, Jin‐Chong; Lloyd, Gareth O.

doi:10.1039/c2cc37428e

Cited by 75 publications

(52 citation statements)

References 64 publications

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“…This is best described using pH and ionic strength dependent state diagrams, which are well known for self-assembled natural spherical or filamentous viruses. 174,[314][315][316][317] Note that pH-dependent self-assembly using synthetic small molecular weight building blocks was already reported earlier by the groups of van Esch, 318 Hartgerink, 319 Goldberger, 306 and others, [320][321][322][323] as well as the ionic strength dependent supramolecular polymerization processes in the Meijer and Rivera groups. [324][325][326][327][328] Importantly, repulsive contributions in supramolecular systems and polymers can also be based on steric constraints, as reported by Stupp, 329 Lee, 330 Hedrick, 331 Fernandez, Schacher, 332 and Besenius.…”

mentioning

confidence: 84%

Controlling supramolecular polymerization through multicomponent self‐assembly

Besenius

2016

J. Polym. Sci. Part A: Polym. Chem.

128

102

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The self-assembly into supramolecular polymers is a process driven by reversible non-covalent interactions between monomers, and gives access to materials applications incorporating mechanical, biological, optical or electronic functionalities. Compared to the achievements in precision polymer synthesis via living and controlled covalent polymerization processes, supramolecular chemists have only just learned how to developed strategies that allow similar control over polymer length, (co)monomer sequence and morphology (random, alternating or blocked ordering). This highlight article discusses the unique opportunities that arise when coassembling multicomponent supramolecular polymers, and focusses on four strategies in order to control the polymer architecture, size, stability and its stimuli-responsive properties: (1) endcapping of supramolecular polymers, (2) biomimetic templated polymerization, (3) controlled selectivity and reactivity in supramolecular copolymerization, and (4) living supramolecular polymerization. In contrast to the traditional focus on equilibrium systems, our emphasis is also on the manipulation of selfassembly kinetics of synthetic supramolecular systems. V C 2016

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mentioning

confidence: 84%

Controlling supramolecular polymerization through multicomponent self‐assembly

Besenius

2016

J. Polym. Sci. Part A: Polym. Chem.

128

102

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“…8,12 Given the fibrous nature of the crystals formed by each of the compounds, the gelation abilities of 1-5 in a variety of solvent conditions were also investigated. Gel formation was not observed under any conditions investigated for the ester derivatives 2 and 4, which generally formed crystalline or micro-crystalline solids upon precipitation.…”

Section: Gelation Studiesmentioning

confidence: 99%

“…[3][4][5][6][7][8][9] Numerous studies into the self-assembly properties of BTAderived structures and their supramolecular polymerization have been carried out, especially by Palmans, Meijer and coworkers. 8,9,10,11 We have recently focused our efforts on the use of BTA-based ligands in the generation of functional soft materials such as lanthanide and transition metal ion based metallogels. 12 We have also employed the BTA unit in the generation of tripodal anion receptors 13 and N-methyl BTA derived platforms for the formation of anion-directed selfassembled cages and self-sorting assemblies.…”

Section: Introductionmentioning

confidence: 99%

Benzene-1,3,5-tricarboxamide n-alkyl ester and carboxylic acid derivatives: tuneable structural, morphological and thermal properties

et al. 2017

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A family of five benzene-1,3,5-tricarboxamide (BTA) compounds with varied side arm functionality [alkyl: n =3, 4 and 5 chains; and ester and carboyxic acids) is reported. Investigations into their self-assembly behaviour revealed the extent to which minor changes in the side arm functionality can affect the structures formed. The carboxylic acid derivatives have a tendency to form gels, while the ester derivatives instead form crystalline phases with associated thermotropic phase transitions. The influence of the side chain length and terminal functional group is rationalised by a combination of single crystal X-ray diffraction studies and examinations of the bulk material properties.

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“…Besenius and coworkers mixed the oppositely charged dendritic peptide amphiphiles in a 1:1 ratio to supramolecular copolymers through a combination of Coulomb attractive forces and hydrogen‐bonding interactions . Lloyd and coworkers reported that a family of aromatic carboxylic acid benzene 1,3,5‐tricarboxamide (BTA) modifications showed spontaneous nucleation and one‐dimensional growth resulting from the molecules stacking into fibers through π ‐stacking interactions and amide–amide hydrogen bonding …”

Section: Introductionmentioning

confidence: 99%

Melamine driven supramolecular self‐assembly of nucleobase derivatives in water

Xiao

Zhang

Lang

2018

J. Polym. Sci. Part A: Polym. Chem.

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Water‐soluble supramolecular polymers, especially made up of biomolecules, are ideally suited to build new biomaterials that can mimic or interact with dynamic, biological environments. Here, two derivatives from thymine (T), that is N‐[2‐(3,4‐Dihydro‐5‐methyl‐2,4‐dioxo‐1(2H)‐pyrimidinyl)acetyl]‐L‐phenylalanine (T‐phe) and N‐(2‐Aminoethyl)‐3,4‐dihydro‐5‐methyl‐2,4‐dioxo‐1(2H)‐pyrimidineacetamide (T‐NH2) were synthesized. Then the optimal condition for self‐assembly of T‐phe and T‐NH2 driven by melamine (M) was explored. It was observed that M/T kept at 1:3 with equivalent T‐phe and T‐NH2 under neutral environment resulted in long fibers (>1 μm) with extremely high aspect ratios, which suggested that electrostatic and π‐stacking interactions could be effectively orchestrated by hydrogen bonds to direct the hierarchical assembly. Furthermore, hydrogels were spontaneously generated with a concentrated solution of T‐phe, T‐NH2, and M due to the fibril entanglement. Given its biomimetic nature and efficient self‐assembly process, this newly developed supramolecular polymer stacked by tetrameric structures represented an innovative concept and pathway for novel bio‐inspired materials. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 789–796

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A family of simple benzene 1,3,5-tricarboxamide (BTA) aromatic carboxylic acid hydrogels

Abstract: We present the characterisation of a hydrogel forming family of benzene 1,3,5-tricarboxamide (BTA) aromatic carboxylic acid derivatives. The simple, easy to synthesise compounds presented here exhibit consistent gel formation at low concentrations through the use of a pH trigger.

Cited by 75 publications

References 64 publications

Controlling supramolecular polymerization through multicomponent self‐assembly

Controlling supramolecular polymerization through multicomponent self‐assembly

Benzene-1,3,5-tricarboxamide n-alkyl ester and carboxylic acid derivatives: tuneable structural, morphological and thermal properties

Melamine driven supramolecular self‐assembly of nucleobase derivatives in water

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