Self-assembly of benzene-tris(bis(p-benzyloxy)triphenylamine)carboxamide

Moulin, Émilie; Busseron, Eric; Domoto, Yuya; Ellis, Thomas; Osypenko, Artem; Maaloum, Mounir; Giuseppone, Nicolas

doi:10.1016/j.crci.2015.05.010

Cited by 4 publications

(3 citation statements)

References 26 publications

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“…In addition, our research group observed waveguiding properties in single crystals of TATA over distances larger than 10 µm. 16 Here, the mechanism proposed to explain such a long range transport was correlated with the presence of metallic electrons in the doped crystals as revealed by their optical, electric, and magnetic properties (Figure 4F,G). Because the waveguiding observed does not amount to a photoluminescence mechanism, we proposed the partial involvement of a plasmonic mechanism.…”

Section: Functional Aspects Of Triarylamine-based Supramolecular Poly...mentioning

confidence: 63%

“…Obviously concentration and temperature also play an important role as is the case for any supramolecular self-assembly. Interestingly, TAA derivatives were shown to produce columnar stacks even when bearing very large substituents in solution, − in thin films, , or in the bulk with the formation of various liquid-crystalline mesophases (Figure F). , Strikingly, even when TAA are conjugated to substituents as large as fullerene moieties, 1D or 3D supramolecular polymers can be obtained (Figure G). , …”

Section: Structural Aspects Of Triarylamine-based Supramolecular Poly...mentioning

confidence: 99%

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Triarylamine-Based Supramolecular Polymers: Structures, Dynamics, and Functions

2019

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Triarylamine molecules and triarylamine-based covalent polymers have been extensively investigated for more than sixty years in academics and industry because of their intriguing electronic and optical characteristics. However, despite the profusion of studies made on these derivatives, only very recently have the first examples of supramolecular polymers based on the triarylamine motif been described in the literature. Specifically, our research group has shown that, by adding supplementary hydrogen bonding moieties such as amide functions in their periphery, it becomes possible to tightly pack triarylamine molecules in columnar supramolecular stacks presenting a collinear arrangement of their central nitrogen atoms. These supramolecular polymers can self-assemble into various soft hierarchical structures such as helical fibers, nanorods, nanospheres, and nanoribbons in the sol and in the gel states, into liquid-crystalline mesophases, as well as into highly organized supramolecular frameworks and their single crystals thereof.Interestingly, the associated supramolecular polymerization mechanism involves a nucleation step MAIN TEXT

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Section: Functional Aspects Of Triarylamine-based Supramolecular Poly...mentioning

confidence: 63%

Section: Structural Aspects Of Triarylamine-based Supramolecular Poly...mentioning

confidence: 99%

Triarylamine-Based Supramolecular Polymers: Structures, Dynamics, and Functions

2019

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“…Some triarylamine derivatives display a photoredox/assembly effect under white light irradiation in chlorinated solvents [ 32 ]. This process has been reported for triarylamines substituted with at least one amide group [ 26 , 32 , 33 , 34 , 35 , 36 , 37 ]. The triarylamines prepared in this work are substituted with alkoxy side chains but do not have amide groups in their structure.…”

Section: Resultsmentioning

confidence: 61%

Triphenylamine-Containing Benzoic Acids: Synthesis, Liquid Crystalline and Redox Properties

et al. 2023

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The synthesis, characterization and liquid crystalline and electrochemical properties of novel triarylamines, in which the triphenylamine platform is non-symmetrically modified with a 4-(6-oxyhexyloxy)benzoic acid group, are reported. Compounds show columnar liquid crystalline behavior, as confirmed through the use of polarized optical microscopy, differential scanning calorimetry and X-ray diffraction. Electrochemical properties were measured using cyclic voltammperometry, obtaining low oxidation potentials and HOMO values that were optimum for consideration as organic semiconductors in hole transport layers. In addition, the photoredox activity of one of these derivatives in dichloromethane was studied under light irradiation. A photooxidation/assembly process under white light irradiation occurs without the assistance of hydrogen bonding amide functional groups.

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Anthranilamide-based Short Peptides Self-Assembled Hydrogels as Antibacterial Agents

Aldilla

Chen

Martin

et al. 2020

Sci Rep

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In this study, we describe the synthesis and molecular properties of anthranilamide-based short peptides which were synthesised via ring opening of isatoic anhydride in excellent yields. These short peptides were incorporated as low molecular weight gelators (LMWG), bola amphiphile, and C3-symmetric molecules to form hydrogels in low concentrations (0.07–0.30% (w/v)). The critical gel concentration (CGC), viscoelastic properties, secondary structure, and fibre morphology of these short peptides were influenced by the aromaticity of the capping group or by the presence of electronegative substituent (namely fluoro) and hydrophobic substituent (such as methyl) in the short peptides. In addition, the hydrogels showed antibacterial activity against S. aureus 38 and moderate toxicity against HEK cells in vitro.

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Self-assembly of benzene-tris(bis(p-benzyloxy)triphenylamine)carboxamide

Cited by 4 publications

References 26 publications

Triarylamine-Based Supramolecular Polymers: Structures, Dynamics, and Functions

Triarylamine-Based Supramolecular Polymers: Structures, Dynamics, and Functions

Triphenylamine-Containing Benzoic Acids: Synthesis, Liquid Crystalline and Redox Properties

Anthranilamide-based Short Peptides Self-Assembled Hydrogels as Antibacterial Agents

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