Twisted conformations in complexes of N-(3-imidazol-1-yl-propyl)-1,8-naphthalimide and fluorescence properties

Nath, Jayashree; Baruah, Jubaraj B.

doi:10.1039/c4qi00028e

Cited by 18 publications

(14 citation statements)

References 59 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In solution, the salts of the imidanap have much different fluorescence emission features from those ones observed from the respective solid samples (Figure ). Conventional fluorescence emission shown by naphthalimide derivatives is observed in imidanap, it shows an emission at 377 nm ( Φ F =0.36) in acetonitrile upon excitation at 320 nm. This emission is photo‐induced electron transfer (PET) OFF state due to the participation of the lone‐pair of electrons on the nitrogen atom of imidazole.…”

Section: Resultsmentioning

confidence: 99%

“…A large numbers of receptors possess lone‐pair of electrons on nitrogen atom of a heterocyclic unit located at a remote site. In such examples fluorescence emission operating through photo‐induced electron transfer are affected by protonation or hydrogen bond formation or by complex formation with metal ions . Modulation of fluorescence of naphthalimide derivatives can be caused by interacting with ions and neutral molecules .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

2018

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

2018

View full text Add to dashboard Cite

show abstract

“…The 2‐(3‐(1H‐imidazol‐1‐yl)propyl)isoindoline‐1,3‐dione (L 1 ) and N,N′‐bis(3‐imidazol‐1‐yl‐propyl)‐pyromelliticdiimide (L 2 ) were synthesized and characterized by reported procedure. The binding abilities of the two compounds were determined in solution by using isothermal calorimetric study.…”

Section: Resultsmentioning

confidence: 97%

Photophysical Properties of Phthalimide and Pyromellitic Diimide Tethered Imidazolium Nitrophenolate Salts

Singh

Baruah

2019

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…Aromatic-imide derivatives are useful to study different π-stacking interactions, − and the impact imparted by such interactions greatly affects the photoluminescence properties of fluorphores in solids. − The progress of aggregation induced emissions in solids has made the emission properties of solids very interesting. − The conformations guided by a substituent contributing to twisted intramolecular charge transfer in aggregates have made significant progress to tune fluorescence emission in self-assembled systems. − Scientists from different backgrounds are focusing attention on tuning signal transductions of naphthalimide derivatives due to their ease in handling and available literature . In a packing pattern, stacking among naphthalimide rings changes significantly in a naphthalimide bearing ligand coordinated to metal ions from corresponding stacking of the free ligand. − The π–π and C–H···O interactions arising due to the naphthalenediimide unit are utilized to modulate the dynamic process in interlocked systems. , Stacking patterns of naphthalimide in ionic derivatives also change with anions. , Depending on coformers in cocrystals and solvent in solvates of naphthalimides, the stacking patterns vary. − The dipolar nature of naphthalimide influences π-stacking, contributing to fluorescence emission in the solid state. , Some of the π-stacking interactions among naphthalimide rings are shown in Figure a. We felt that introducing a pyridyl-amide group that possesses an additional nitrogen atom containing ring would enhance the impact of such a study through modulation of the orientation of the amide group.…”

Section: Introductionmentioning

confidence: 99%

Changing π-Interactions and Conformational Adjustments of N-(Isonicotinylhydrazide)-1,8-naphthalimide by Hydration and Complexation Affect Photophysical Properties

Tarai

Baruah

2017

Crystal Growth & Design

Self Cite

View full text Add to dashboard Cite

Noncovalent self-assemblies of different forms of a 1,8-naphthalimide derivative N-(isonicotinylhydrazide)-1,8-naphthalimide adopt different conformational adjustments due to the interplay of weak interactions. In such assemblies stacking interactions significantly contribute to direct the orientations of tether, which also influenced packing patterns. Effects of weak noncovalent interactions are reflected in the physicochemical properties of solvate and metal complexes of this naphthalimide derivative. Dual fluorescence emissions were observed from hydrate and silver complex of N-(isonicotinylhydrazide)-1,8-naphthalimide, which was not observed in anhydrous form of the compound. These results are compared with fluorescence emission study performed with solution of N-(isonicotinylhydrazide)-1,8-naphthalimide. Aggregation induced fluorescence emission of a solution in DMSO was caused by adding water. This emission in solution occurred at a much different emission wavelength than the emission observed from the hydrated sample in the solid state. It is also established that the aggregation induced fluorescence of N-(isonicotinylhydrazide)-1,8-naphthalimide caused by adding water to a solution of the compound in dimethyl sulfoxide can be quenched by different nitro-phenols.

show abstract

Twisted conformations in complexes of N-(3-imidazol-1-yl-propyl)-1,8-naphthalimide and fluorescence properties

Abstract: A series of complexes of N-(3-imidazol-1-yl-propyl)-1,8-naphthalimide (L) with divalent ions of manganese, cobalt, zinc, cadmium and mercury are structurally characterized.

Cited by 18 publications

References 59 publications

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

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

Changing π-Interactions and Conformational Adjustments of N-(Isonicotinylhydrazide)-1,8-naphthalimide by Hydration and Complexation Affect Photophysical Properties

Contact Info

Product

Resources

About