Luminescence studies of o-hydroxy p-amino and p-dimethylamino methyl benzoate

Aleksiejew, Marek; Heldt, J.

doi:10.1016/j.jlumin.2007.12.036

Cited by 17 publications

(4 citation statements)

References 35 publications

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“…1 and Table 2 ). It has been shown [ 7 , 8 ] that the calculated S 0 → S 1 transition in the studied compounds is described by the same linear combination of HOMO and LUMO one electron π-orbital transitions (only with different composition) as the S 0 ( 1 A ) → S 1 ( 1 L b ) band of benzene and MB (methyl benzoate). Additionally, the strong peak located at 211 nm (47,400 cm −1 ) for II and at 215 nm (46,500 cm −1 ) for III (see Fig.…”

Section: Resultsmentioning

confidence: 91%

“…1 and Table 2 ). Despite the fact that the theoretical calculations suggest only one transition in the long-wavelength absorption spectrum in THF solution the long-wavelength band consists of two transitions pictured by Gaussian profiles [ 7 , 8 ], possessing maxima at 304.9 nm and 291.3 nm for I, 309.9 nm and 288.2 nm for II and 318.7 nm and 299.3 nm for III, respectively. It is important to note here that these two transitions undergo an energy-level reversal of the charge transfer and normal electronic transitions upon the environment change from vapour phase to the solvents [ 8 , 22 – 24 ].…”

Section: Resultsmentioning

confidence: 97%

“…Since our earlier papers [ 7 , 8 ] concern spectroscopic studies of methyl p-dimethylaminobenzoate and its ortho derivatives, it is very interesting to study the influence of the H + ion concentration on the steady-state absorption and fluorescence spectra of methyl p-dimethylaminobenzoate (I) and its o-methoxy (II), o-hydroxy (III) derivatives. The chemical structures of compounds of interest are given in Scheme 1 .…”

Section: Introductionmentioning

confidence: 99%

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Influence of Prototropic Reactions on the Absorption and Fluorescence Spectra of Methyl p-dimethylaminobenzoate and Its Two Ortho Derivatives

et al. 2011

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The influence of prototropic reactions on the spectral characteristics of methyl p-dimethylaminobenzoate (I) and its o-methoxy (II) and o-hydroxy (III) derivatives has been studied using steady-state spectroscopic technique and quantum-chemical calculations. This study concerns the solvent-induced shift of the absorption, locally excited (LE) and intramolecular charge transfer (ICT) fluorescence bands in the neat tetrahydrofuran (THF) and its hydrochloric acid solutions at different HCl concentrations. On the basis of the experimental results and quantum-chemical calculations, it was shown that in a hydrochloric acid solution the studied molecules exist as a mixture of neutral, mono-, and dicationic forms. Additionally, the results of spectroscopic measurements were used to calculate, according to the Benesi-Hildebrand method, the equilibrium constants of protopropic reactions in the ground, S0, and excited, S1, states. Our findings predestine molecules I and II to be used as acid fluorescence probes in a region of 0–2.5 M of [H+] concentrations.

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Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

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Influence of Prototropic Reactions on the Absorption and Fluorescence Spectra of Methyl p-dimethylaminobenzoate and Its Two Ortho Derivatives

et al. 2011

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“…In this paper, we mainly selected two derivatives with different substituents (PASE: p -aminosalicylic acid methyl ester and PDASE: p -dimethylaminosalicylic acid methyl ester) as research objects to explore the intrinsic relationship between ICT and IPT. A series of experiments have studied the spectral properties of these molecules in different polar solvents and the conformational changes between the ground state ( S 0 ) and excited state ( S 1 ). ,,,− For example, Gormin and Kasha experimentally observed three different fluorescence emissions starting from the common initial singlet excited state of 2-hydroxy-4-dimethylaminobenzoic acid methyl ester . At present, research studies on these derivatives were mainly focused on experiments. , However, the theoretical details of the proton transfer reaction mechanism of these molecules in aqueous solvents and the relationship between IPT and ICT have been reported rarely.…”

Section: Introductionmentioning

confidence: 99%

Effects of Twisted Intramolecular Charge Transfer Behavior on Excited-State Intramolecular Proton Transfer Reactions of Methyl Benzoate Derivatives in Water Solution

et al. 2022

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Many methyl benzoate derivatives were found to show intramolecular charge transfer (ICT), intramolecular proton transfer, and other properties, which have extensive applications in lasing media, metal ion sensors, active materials, and fluorescence probe fields. However, the intrinsic relationship and reaction mechanism between the excited-state intramolecular proton transfer (ESIPT) and ICT between methyl benzoate derivatives with different substituents have not been explained. In this paper, the density functional theory and time-dependent density functional theory methods were used to study the ESIPT and ICT behaviors of p-aminosalicylic acid methyl ester and p-dimethylaminosalicylic acid methyl ester in water and obtain the intrinsic interaction between the two behaviors. The bond parameters, infrared spectra, reduced density gradient scatter plots, and topological analyses of these two molecules in the ground state and excited state were analyzed to confirm the enhancement of the excited-state intramolecular hydrogen bonds (IHBs). The simulated absorption and fluorescence spectra of these molecules agreed well with the experimental values. Based on the optimized structure, we also plotted the natural transition orbitals, electron density difference maps, and frontier molecular orbitals (FMOs), which showed the changes of the charge distribution of these molecules intuitively upon photoexcitation. In addition, we also found that the degree of IHB enhancement with −N(CH3)2 substituents was less than that with −NH2, reflecting an inhibition effect of twisted intramolecular charge transfer (TICT) on ESIPT reaction. This conclusion was confirmed by our calculated potential energy curves. This work may better deepen the comprehension of the intrinsic relationship between ESIPT and TICT behavior and sequentially provide better theoretical guidance for the synthesis of fluorescent molecules related to these two behaviors.

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An Acid‐Responsive Single Trichromatic Luminescent Dye That Provides Pure White‐Light Emission

et al. 2017

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A novel acid‐responsive single trichromatic luminescent dye capable of emitting pure white light (WL) is reported. A newly designed p‐phenylene‐bridged bipyrrole bearing N‐alkylimino groups (1 a) specifically provides WL emission upon mixing with trifluoroacetic acid (TFA) in a CH2Cl2 solution. The emission originates from the trichromatic luminescent behavior of 1 a upon protonation of the imino groups. The blue‐light‐emitting 1 a exhibits dramatic color changes in fluorescence to orange and green upon mono‐ and diprotonation, respectively, providing a wide emission band in the range of λ=400–800 nm that provide WL when the compound is in a dynamic equilibrium between the three states. The sample also exhibits low self‐absorption of the emitted light and a high fluorescence quantum yield upon excitation with UV light.

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Luminescence studies of o-hydroxy p-amino and p-dimethylamino methyl benzoate

Cited by 17 publications

References 35 publications

Influence of Prototropic Reactions on the Absorption and Fluorescence Spectra of Methyl p-dimethylaminobenzoate and Its Two Ortho Derivatives

Influence of Prototropic Reactions on the Absorption and Fluorescence Spectra of Methyl p-dimethylaminobenzoate and Its Two Ortho Derivatives

Effects of Twisted Intramolecular Charge Transfer Behavior on Excited-State Intramolecular Proton Transfer Reactions of Methyl Benzoate Derivatives in Water Solution

An Acid‐Responsive Single Trichromatic Luminescent Dye That Provides Pure White‐Light Emission

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