Cyclic aromatic imides as a potential class of molecules for supramolecular interactions

Nath, Jayashree; Baruah, Jubaraj B.

doi:10.1039/c5ce01485a

Cited by 22 publications

(16 citation statements)

References 182 publications

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“…The synthesis and characterization of the PMDI-Fe 3 O 4 nanoparticles used herein have been carried out using the methodology described in the literature by others. 34 The synthesis and characterization of the PDI-Fe 3 O 4 hybrid nanoparticles have been previously described by us. 32 Reagents and solvents required for the synthesis of the new NDI–Fe 3 O 4 nanoparticles were purchased from Sigma-Aldrich and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Influence of the aromatic surface on the capacity of adsorption of VOCs by magnetite supported organic–inorganic hybrids

et al. 2019

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It has been recently evidenced that hybrid magnetic nanomaterials based on perylene diimide (PDI) dopamine and iron oxide nanoparticles are useful for the adsorption and determination of volatile organic compounds (VOCs). However, NDI compounds are expensive and difficult to handle compared to smaller size diimides. Therefore, in this manuscript a combined experimental and theoretical investigation is reported including the analysis of the effect of changing the aromatic surface on the ability of these magnetite supported organic-inorganic hybrid nanoparticles (NPs) to adsorb several aromatic and non-aromatic VOCs. In particular, two new hybrid Fe 3 O 4 NPs are synthesized and characterized where the size of organic PDI dopamine linker is progressively reduced to naphthalene diimide (NDI) and pyromellitic diimide (PMDI). These materials were utilized to fill two sorbent tubes in series. Thermal desorption (TD) combined with capillary gas chromatography (GC)/flame detector (FID) was used to analyze both front and back tubes. Adsorption values (defined as % VOCs found in the front tube) were determined for a series of VOCs. The binding energies (DFT-D3 calculations) of VOC-Fe 3 O 4 NP complexes were also computed to correlate the electron-accepting ability of the arylene diimide (PDI, NDI or PMDI) with the adsorption capacity of the different tubes. The prepared hybrids can be easily separated magnetically and showed great reusability. † Electronic supplementary information (ESI) available: SEM micrographic images, DLS size distribution and zeta potential of all hybrid nanoparticles used in this work. 1 H-NMR and 13 C-NMR spectra of the imide-dopamine compounds and IR spectra of all compounds used in this manuscript. See Scheme 1 PMDI (1), NDI (2) and PDI (3) derivatives used to functionalize the Fe 3 O 4 NP. VOCs 4 to 9 used in this study.This journal is

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Section: Methodsmentioning

confidence: 99%

Influence of the aromatic surface on the capacity of adsorption of VOCs by magnetite supported organic–inorganic hybrids

et al. 2019

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“…27 These interactions are common in poly-aromatic compounds to guide the mechanism of photoluminescence processes. [28][29][30] Stacked arrangements through p-interactions contribute to dimer-and excimerlike emissions [31][32][33][34] and Dexter quenching. 35 Different types of aggregates where different packings through the C-H/p interactions or p-p interactions are present show distinguishable features.…”

Section: Introductionmentioning

confidence: 99%

Stacking among the clips of the poly-aromatic rings of phenazine with hydroxy-aromatics and photophysical properties

2019

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Clip-like arrangements of molecules in the cocrystals of phenazine with hydroxy-aromatics in their respective self-assemblies and photophysical properties were presented. Phenazine cocrystals with 1,2dihydroxybenzene provided assembly with butterfly-like arrangements. In these cocrystals, the phenazine molecules occurred in parallel pairs having extensive p-stacking. The clip-like cocrystals with 1,3-dihydroxybenzene also exhibited parallel pairs of phenazine molecules that were parallel cofacial pstacked. The hydrated cocrystals of phenazine with 1,2,3-trihydroxybenzene had chains of parallel cofacial phenazine rings having three distinguishable p-separation distances among the centroids of the phenazine rings. Also, 2,7-dihydroxynaphthalene formed a clip-like cocrystal with phenazine, which encapsulated an additional molecule of phenazine. This cocrystal also provided chain-like parallel arrangements of the phenazine molecules. The emission and quantum yields of the cocrystals were determined by the integrating sphere method, which indicated that only the cocrystal of phenazine with 2,7-dihydroxynaphthalene showed monomer-like emission of phenazine and the rest of the cocrystals were in a quenched state. In the solution phase, quenching of the emission of hydroxynaphthalene was observed when phenazine was added to an independent solution of 2,7-dihydroxynaphthalene or another hydroxynaphthalene. However, when hydroxybenzenes were added to a solution of phenazine, fluorescence enhancements of phenazine occurred due to photo-electron transfer. Fig. 1 (a) Some possible hydrogen-bonded assemblies of phenazine with aromatic diols and (b) structures of phenazine and different organic aromatic diols used in this study.33404 | RSC Adv., 2019,9,[33403][33404][33405][33406][33407][33408][33409][33410][33411][33412] This journal is

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“…Rylenes belongs to a class of compounds that are comprised of frameworks of naphthalene units linked at peri ‐positions. In this class of compounds π‐interactions influence various physical and chemical properties . Among them the naphthalimide containing compounds are inherently dipolar π‐systems which stack among themselves or stacks with other aromatic π‐systems that are either electron rich or electron deficient .…”

Section: Introductionmentioning

confidence: 99%

Changes in Emission Properties by π‐Stacking and Conformation Adjustment of an Imidazole‐Tethered Naphthalimide Derivative

2018

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Solid state self-assemblies of 2,4-dinitrophenolate, 2,4,6-trinitrophenolate salts of N-(3-imidazol-1-yl-propyl)-1,8-naphthalimide (abbreviated as imidanap) have distinguishable p-stacking patterns, each stack influences fluorescence emission causing fluorescence quenching. It is found that the solid sample of nitrate or bromide salt of imidanap retains fluorescence properties of the parent compound. Photo-induced electron transfer process in solution gets prominence upon interactions of imidanap with hydrobromic as well as nitric acid but in the nitrophenolate salts the effect of p-interactions over-ride the effect of protonation of imidazole to change intensity of fluorescence emission. DFT calculations using B3LYP functional with 6-31 + G (d,p) as basis set have revealed LUMO in the imidanap and in the respective nitrophenolate salts are localized on the naphthalimide unit whereas HOMO in each case is localization differently over the rings other than the naphthalimide ring. Studies based on 1 H NMR suggest that water causes conformation adjustments of imidanap by forming hydrogen bonds. This enhances photo-induced electron transfer (PET) emission of the imidanap until a limiting concentration of water is reached, beyond which increase in amount of water causes quenching of emission. The PET-ON state of imidanap generated by addition of water to an acetonitrile solution is quenched by 2,4,6-trinitrophenol due to charge-transfer interactions.

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Cyclic aromatic imides as a potential class of molecules for supramolecular interactions

Abstract: Prospects of stacking interactions of imides beneficial to generation of new soft materials are projected by analysing examples of primary building blocks that provide a basis for understanding at the molecular level.

Cited by 22 publications

References 182 publications

Influence of the aromatic surface on the capacity of adsorption of VOCs by magnetite supported organic–inorganic hybrids

Influence of the aromatic surface on the capacity of adsorption of VOCs by magnetite supported organic–inorganic hybrids

Stacking among the clips of the poly-aromatic rings of phenazine with hydroxy-aromatics and photophysical properties

Changes in Emission Properties by π‐Stacking and Conformation Adjustment of an Imidazole‐Tethered Naphthalimide Derivative

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