Extended supramolecular organization of π-systems using yet unexplored simultaneous intra- and inter-molecular H-bonding motifs of 1,3-dihydroxy derivatives

Mondal, Tathagata; Basak, Durga; Ouahabi, Abdelaziz Al; Schmutz, Marc; Mésini, Philippe J.; Ghosh, Suhrit

doi:10.1039/c4cc10335a

Cited by 18 publications

(19 citation statements)

References 46 publications

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“…Complete dissolution of the gel upon addition of a protic solvent (5 % MeOH) confirmed the decisive role of H‐bonding on the supramolecular assembly process. In fact, neither NDI‐2 nor NDI‐3 (Scheme ) exhibit gelation ability under similar conditions, which suggests the necessity of the 1,3‐dihydroxyl motif for the extended H‐bonded chain formation as exemplified in our previous report …”

Section: Resultsmentioning

confidence: 75%

“…Both G' and G'' remained constant up to ac ertain applieds tress,s uggesting gel-like behavior.B eyondacritical point, they cross each other and show deviation from linearityi ndicating al iquid-like flow.T he yield stress (cross over point) of the (R)-NDI gel wase stimated to be 18.3 Pa indicatingarather strong gelation that can be attributed to the synergistic effect of H-bonding and aromatic interactions. FTIR spectra of the gel in TCE revealed ap rominent peak at 3319 cm À1 ,w hich is characteristic of the H-bonded ÀOH, [11] which is missing in the spectrum in CHCl 3 (Figure 1b)i nw hich the chromophore remains in the monomeric form. Variabletemperature FTIR studies with the gel sample showeda lmost no variation of this peak even at 80 8Cc onfirming thermally stable H-bonding among the hydroxyl groups (Figure S1, Supporting Information).…”

Section: Self-assemblya Nd Gelationmentioning

confidence: 99%

“…In fact, neither NDI-2 nor NDI-3 (Scheme 1) exhibit gelation ability under similar conditions, which suggestst he necessity of the 1,3-dihydroxyl motif for the extended H-bonded chain formation as exemplified in our previousreport. [11] Structure in the solid state…”

Section: Self-assemblya Nd Gelationmentioning

confidence: 99%

“…The majority of the examples of H‐bonding promoted supramolecular polymerization of NDI or other π‐systems utilize amide or urea groups that work in tandem along the direction of π‐stacking. Recently we have identified that the 1,3‐dihydroxy functional group can facilitate supramolecular polymerization of an attached chromophore by combination of simultaneous intra‐ and intermolecular H‐bonding interactions . For example, NDI‐1 (Scheme ) can spontaneously produce a fibrillar gel in aliphatic hydrocarbon solvents.…”

Section: Introductionmentioning

confidence: 99%

“…Recently we have identified that the 1,3-dihydroxy functional group can facilitate supramolecular polymerization of an attached chromophore by combination of simultaneous intra-and intermolecular H-bonding interactions. [11] For example,N DI-1 (Scheme 1) can spontaneously produce af ibrillar gel in aliphatic hydrocarbon solvents. The specific H-bonding motif among this functional group resulted in a1 Dc hain formation with the attached chromophores located as pendant to the supramolecular polymer backbone.…”

Section: Introductionmentioning

confidence: 99%

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Supramolecular Chirality Issues in Unorthodox Naphthalene Diimide Gelators

Ghosh

Paul

Sakurai

et al. 2018

Chemistry A European J

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Herein, the self-assembly of a few 1,3-dihydroxyl functionalized naphthalene diimide (NDI) derivatives has been reported with particular emphasis on the impact of chirality on gelation and the effect of self-assembly on charge-carrier mobility. A nonconventional gelator (R)-NDI, devoid of any long alkyl chains, exhibited spontaneous gelation in tetra-chloroethylene (TCE). Based on X-ray crystallography and powder X-ray diffraction studies, it was established that a ladder-like hydrogen-bonded chain formation between the 1,3-dihydroxyl group leads to the fibrillar structures with preferential helicity. Likewise the (S)-isomer also exhibited identical gelation and mesoscopic structure but produced fibrils with the opposite handedness. Intriguingly, an equimolar mixture of the (R)- and (S)-isomers did not show any gelation ability, rather a macroscopic precipitation was observed and, in sharp contrast to the individual isomers, the morphology of the mixture showed ill-defined near spherical agglomerates. Differential scanning calorimetry (DSC) studies revealed an identical crystallization peak for the supramolecular polymer produced from the enantiopure gelators ((R)- or (S)-isomer), which was absent in their equimolar mixture. However, mixtures of the two isomers with enantiomeric excess retrieved the gelation ability and preferential helicity demonstrating that chiral amplification is operative in the present system through the so-called "majority rule" effect. Chirality induction was also realized by the "sergeant and soldier" principle in the supramolecular assembly of an achiral NDI gelator in the presence of either the (R)- or (S)-isomer as the chiral dopant. However, the strong helical bias induced by the chiral gelator was found to be opposite in nature compared to that found in the self-assembly of the pure chiral gelator that has been rarely reported in the literature. Flash-photolysis time-resolved microwave conductivity (FP-TRMC) measurements indicated the strong positive impact of the gelation on the electrical conductivity.

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Section: Resultsmentioning

confidence: 75%

Section: Self-assemblya Nd Gelationmentioning

confidence: 99%

Section: Self-assemblya Nd Gelationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Supramolecular Chirality Issues in Unorthodox Naphthalene Diimide Gelators

Ghosh

Paul

Sakurai

et al. 2018

Chemistry A European J

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Construction of Pillar[5]arene Tetramer‐Based Cross‐Linked Supramolecular Polymers through Hierarchical Charge‐Transfer and Host‐Guest Interactions

et al. 2018

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A pillar [5]arene tetramer was constructed by naphthalene diimide and naphthalene-bridged pillar [5] arene dimers through X-type charge transfer interactions. Furthermore, by adding a ditopic neutral guest, a crosslinked supramolecular polymer was successfully fabricated. These cross-linked polymers were confirmed by concentration-dependent NMR spectroscopy, DOSY NMR, UV, SEM and viscosity measurements.

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Observation of Supramolecular Chirality in a Hierarchically Self‐Assembled Mixed‐Stack Charge‐Transfer Complex

Krishnan

Gopidas

2017

Chemistry A European J

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Supramolecular chirality was observed in a charge-transfer (CT) complex formed by self-assembly of β-cyclodextrin-linked pyrene and adamantane-linked pyromellitic diimide in water. In the complex, the pyrene-pyromellitic diimide CT interaction is reinforced several-fold by the strong β-cyclodextrin-adamantane inclusion binding interaction, as confirmed by H NMR, absorption, fluorescence and isothermal titration calorimetry studies. The CT complex exhibited high stability, as inferred from the temperature-dependent absorption and NMR studies. The CT absorption band exhibited a positive Cotton effect indicative of supramolecular chirality for the complex. Twisted fibres were observed in TEM, AFM, and SEM experiments. A mechanism involving synergistic binding interactions leading to 2D sheets, followed by twisting of the sheet, is proposed for the formation of twisted fibres. This system offers a chance to investigate a combination of supramolecular CT and supramolecular chirality and explore their synergistic effects.

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Extended supramolecular organization of π-systems using yet unexplored simultaneous intra- and inter-molecular H-bonding motifs of 1,3-dihydroxy derivatives

Cited by 18 publications

References 46 publications

Supramolecular Chirality Issues in Unorthodox Naphthalene Diimide Gelators

Supramolecular Chirality Issues in Unorthodox Naphthalene Diimide Gelators

Construction of Pillar[5]arene Tetramer‐Based Cross‐Linked Supramolecular Polymers through Hierarchical Charge‐Transfer and Host‐Guest Interactions

Observation of Supramolecular Chirality in a Hierarchically Self‐Assembled Mixed‐Stack Charge‐Transfer Complex

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