Specific optical signalling of anions via intramolecular charge transfer pathway based on acridinedione fluorophore

Thiagarajan, Viruthachalam; Ramamurthy, P.

doi:10.1016/j.jlumin.2007.01.003

Cited by 27 publications

(19 citation statements)

References 45 publications

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“…The binding constant was estimated to be 3275 m À1 from the linear relationship obtained in the Benesi-Hildebrand plot [19] (Figure 2). 4 À , H-bonded complex of F À shows the red shift in the absorption maximum, but the deprotonation of the thiourea NH leads to the formation of a new peak, which is confirmed by observing similar peak on the addition of HO À ( Figure S5a).…”

Section: Resultssupporting

confidence: 55%

“…On complete complexation of 1 with AcO À shows a single exponential decay with the lifetime of 5.68 ns ( Figure S9). Whereas in the presence of H 2 PO 4 À , such a complete complexation is not observed. Even after the addition of higher concentrations of H 2 PO 4 À , the fluorescence decay was found to be triexponential with the lifetime of 0.35 ns (6.0 %), 2.81 ns (7.8 %) and 4.67 ns (86.2 %) ( Figure S10).…”

Section: Resultsmentioning

confidence: 90%

“…Even after the addition of higher concentrations of H 2 PO 4 À , the fluorescence decay was found to be triexponential with the lifetime of 0.35 ns (6.0 %), 2.81 ns (7.8 %) and 4.67 ns (86.2 %) ( Figure S10). This clearly indicates that the H-bonding interaction of H 2 PO 4 À with the thiourea receptor is relatively weak, when compared to F À and AcO À . Therefore the free ADDTU 1 exists in the system in addition to the H-bonded complex of 1.H 2 PO 4 À .…”

Section: Resultsmentioning

confidence: 94%

“…The reaction mixture was diluted with water (100 mL) and allowed to stand overnight; the tetraketone 1 a was collected by filtration, dried and recrystallized from methanol to yield pure 1 a (5.36 g, 94 %). 3,6,4,6,7,9, www.chemeurj.org…”

Section: -Methoxybenzylidene Bisdimedone (1 A)mentioning

confidence: 99%

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Fluorescence Spectroscopic Evidence for Hydrogen Bonding and Deprotonation Equilibrium between Fluoride and a Thiourea Derivative

Ashokkumar

Ramakrishnan

Ramamurthy

2010

Chemistry A European J

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Interaction of anions with thiourea-linked acridinedione fluorophore was studied by absorption, (1)H NMR, steady-state and time-resolved fluorescence techniques. Addition of AcO(-) and H(2)PO(4)(-) shows a genuine H-bonded complex with thiourea receptor; whereas, F(-) shows stepwise H-bonding and deprotonation of thiourea NH as confirmed by (1)H NMR titration. Free receptor 1 shows emission maximum at 418 nm; whereas, H-bonded complex of 1·F(-) shows a new redshifted emission maximum at 473 nm and the deprotonated 1 exhibits an emission peak at 502 nm. Presence of these three different emitting species was probed by 3D emission spectroscopic studies. Equilibrium between the free receptor 1, 1·F(-) H-bonded complex and deprotonated 1 was confirmed by time-resolved fluorescence studies. Time-resolved area normalised emission spectra (TRANES) of 1 in the presence of F(-) shows two isoemissive points at 456 and 479 nm between time delays of 0-0.5 ns and 1-20 ns, respectively, due to the existence of three emitting species in equilibrium. Observation of such an equilibrium based on fluorescence spectroscopic studies further proves the earlier reported absorption and (1)H NMR spectroscopic studies of H-bonding and deprotonation processes and also illustrates the dynamics of anion-receptor interactions.

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Section: Resultssupporting

confidence: 55%

Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 94%

Section: -Methoxybenzylidene Bisdimedone (1 A)mentioning

confidence: 99%

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Fluorescence Spectroscopic Evidence for Hydrogen Bonding and Deprotonation Equilibrium between Fluoride and a Thiourea Derivative

Ashokkumar

Ramakrishnan

Ramamurthy

2010

Chemistry A European J

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“…Generally, the design of fluorescent chemosensors is mainly based on photoinduced electron/energy transfer (PET) [8], metal-ligand charge transfer (MLCT) [9], intramolecular charge transfer (ICT) [10], excimer/exciplex formation [11], guest-induced changes in the rigidity of the host molecules [12][13][14] and so on. Currently, the development of fluorescent anion receptors is an active field in supramolecular chemistry due to its high sensitivity and simplicity [15].…”

Section: Introductionmentioning

confidence: 99%

A turn-on fluorescent anion receptor based on N,N′-di-β-naphthyl-1,10-phenanthroline-2,9-diamide

Shao

Qiao

Lin

et al. 2008

Journal of Luminescence

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Head‐to‐Tail Intermolecular Hydrogen Bonding of OH and NH Groups with Fluoride

2011

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To explore the anion-recognition ability of the phenolic hydroxyl group and the amino hydrogen, we synthesized three different acridinedione (ADD) based anion receptors, 1, 2 and 3, having OH, NH, and combination of OH and NH groups, respectively. Absorption, emission and (1)H NMR spectral studies revealed that receptor 1, having only a phenolic OH group, shows selective deprotonation of the hydroxyl proton towards F(-), which results in an "ON-OFF"-type signal in the fluorescence spectral studies. Receptor 2, which only has an amino hydrogen, also shows deprotonation of the amino hydrogen with F(-), whereas receptor 3 (having both OH and NH groups) shows head-to-tail intermolecular hydrogen bonding of OH and NH groups with F(-) prior to deprotonation. The observation of hydrogen bonding of the OH and NH groups in a combined solution of 1 and 2 with F(-) in a head-to-tail hetero-intermolecular fashion, and the absence of head-to-head and tail-to-tail intermolecular hydrogen bonding in 1 and 2 with F(-), prove that the difference in the acidity of the OH and NH protons leads to the formation of an intermolecular hydrogen-bonding complex with F(-) prior to deprotonation. The presence of this hydrogen-bonding complex was confirmed by absorption spectroscopy, 3D emission contour studies, and (1)H NMR titration.

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Specific optical signalling of anions via intramolecular charge transfer pathway based on acridinedione fluorophore

Cited by 27 publications

References 45 publications

Fluorescence Spectroscopic Evidence for Hydrogen Bonding and Deprotonation Equilibrium between Fluoride and a Thiourea Derivative

Fluorescence Spectroscopic Evidence for Hydrogen Bonding and Deprotonation Equilibrium between Fluoride and a Thiourea Derivative

A turn-on fluorescent anion receptor based on N,N′-di-β-naphthyl-1,10-phenanthroline-2,9-diamide

Head‐to‐Tail Intermolecular Hydrogen Bonding of OH and NH Groups with Fluoride

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