Resonance Energy Transfer Emission Observed in Cocrystal of N,N′-Bis(3-imidazol-1-ylpropyl)naphthalenediimide with Cinnamic Acid

Tarai, Arup; Baruah, Jubaraj B.

doi:10.1002/slct.201702214

Cited by 4 publications

(5 citation statements)

References 44 publications

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“…In our case the angle between the two planes is 37° (Fig 2b). Our recent study and other reports suggest that π‐systems without a stacking arrangement between aromatic rings of the donor and acceptor counterparts are suitable for showing fluorescence emission that appear at much different wave lengths from the emission of the individual fluorophores. We find that the compound pyrbenth does not have π‐stacking interactions in its packing pattern which are reflected from the anlaysis of the centroid to centroid distances among the rings that are parallel with respect to each other in the lattice.…”

Section: Resultsmentioning

confidence: 63%

“…Pyrene derivatives are utilised as biological probes as certain one of them shows fluorescence emission through Forster resonance energy transfer . Our interest has been on the interplay of weak interactions to generate interesting photoluminescence properties have suggested us that in solid state crystal packing pattern which lacks π‐stacking among donors or acceptors or their combinations can cause resonance energy transfer to show emission at a longer wavelength . On the other hand, it is a known fact that intramolecular charge transfer emission process may be quenched or enhanced by specific oxidation state of particular metal ion and such process was demonstrated to distinguish fluorophoric positional isomers .…”

Section: Introductionmentioning

confidence: 99%

“…[26] Our interest has been on the interplay of weak interactions to generate interesting photoluminescence properties have suggested us that in solid state crystal packing pattern which lacks p-stacking among donors or acceptors or their combinations can cause resonance energy transfer to show emission at a longer wavelength. [27] On the other hand, it is a known fact that intramolecular charge transfer emission process may be quenched or enhanced by specific oxidation state of particular metal ion and such process was demonstrated to distinguish fluorophoric positional isomers. [28] It is also an established fact that when wavelength of emission of a donor overlaps with the fluorescence emission of acceptor there is like to have resonance energy transfer to shift the emission to longer wavelength from the emission wavelength of individual components.…”

Section: Introductionmentioning

confidence: 99%

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Emission of Pyrene Connected to Benzothiazole Unit via Resonance and Intramolecular Charge Transfer

2018

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The compound 2‐(pyren‐1‐yl)benzo[d]thiazole has two independent fluorescent components connected directly through C−C bond; each component has fluorescence emission at comparable wavelengths. Fluorescence emission of this compound in solution is completely different from the fluorescence emission observed from solid sample. Solid sample of the compound shows emission at 555 nm with a large Stoke's shift 180 nm; this emission is attributed to resonance energy transfer between donor and acceptor components. Compound in solution shows intramolecular charge transfer emissions at 425 nm and 443 nm; such emissions in solution of the compound are quenched on addition of water; whereas these emissions are enhanced by stannic ions. The reasons for quenching of emission by water are studied by 1H NMR experiments, fluorescence emission decay study and micro‐calorimetric titrations.

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Section: Resultsmentioning

confidence: 63%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Emission of Pyrene Connected to Benzothiazole Unit via Resonance and Intramolecular Charge Transfer

2018

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“…Modulation of fluorescence of naphthalimide derivatives can be caused by interacting with ions and neutral molecules . We have been studying molecular recognitions, ion recognitions and conformational aspects of imide containing compounds that have nitrogen based heterocyclic units attached through flexible tethers . Those studies have been carried out with a philosophy that a flexible tether either keeps away or brings close to a fluorophore from an interacting group located at a remote site.…”

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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“…The emission quenching were observed in the salts nitro‐phenolic compounds with different fluorescent heterocycles . Hence, less significant host dependent emission quenching shown by a particular nitrophenolic compound with different imidazole tethered imide hosts suggested an intermolecular quenching mechanism.…”

Section: Resultsmentioning

confidence: 99%

Photophysical Properties of Phthalimide and Pyromellitic Diimide Tethered Imidazolium Nitrophenolate Salts

Singh

Baruah

2019

ChemistrySelect

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Structural aspects of the salt of 2-(3-(1H-imidazol-1-yl)propyl) isoindoline-1,3-dione (L 1 ) with 2,4,6-trinitrophenol as well as the salts of N,N'-bis(3-imidazol-1-yl-propyl)-pyromelliticdiimide (L 2 ) with 2,4-dinitrophenol (H24dnp) and 2,4,6-trinitrophenol (H246tnp) are reported along with the solid and solution studies on the photophysical properties of these salts. The fluorescence emission of the L 1 and L 2 are quenched by H24dnp and H246tnp both in solid and in solution. In solution the L 1 has comparable binding constant with H24dnp and H246tnp but the relative ability to quench the fluorescence emission of L 1 by H24dnp is less than the quenching abilities of the H246tnp. These two nitrophenols independently do not distinguish the L 1 from L 2 but the extent of quenching caused independently by the H24dnp or H246tnp on L 1 or L 2 make them easily distinguishable. Addition of water quenches the fluorescence emission of L 1 and L 2 ; but the addition of water to solution of the nitrophenolate salts result in the recovery of fluorescence emissions from the quenched states. The salts in solid state have short emission life-times. The PET effect prominently caused by mineral acids on L 1 or L 2 is not observed in the nitrophenolate salts. In solid state the O-π interactions contributed to stacking of the aromatic in the 2,4,6-trinitrophenolate salt of L 2 , hence it is non-fluorescent.

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Resonance Energy Transfer Emission Observed in Cocrystal of N,N′-Bis(3-imidazol-1-ylpropyl)naphthalenediimide with Cinnamic Acid

Cited by 4 publications

References 44 publications

Emission of Pyrene Connected to Benzothiazole Unit via Resonance and Intramolecular Charge Transfer

Emission of Pyrene Connected to Benzothiazole Unit via Resonance and Intramolecular Charge Transfer

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

Photophysical Properties of Phthalimide and Pyromellitic Diimide Tethered Imidazolium Nitrophenolate Salts

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