Influence of polarity of medium on fluorescence characteristics of alkylaminobenzophenones

Kotsyuba, T. S.; Granchak, V. M.; Dilung, I. I.; Kondilenko, V. P.

doi:10.1007/bf02764741

Cited by 3 publications

(6 citation statements)

References 5 publications

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“…In solutions containing water percentages up to 40%, a gradual increase in a green fluorescence peak at around 555 nm was apparent (excitation ≈430 nm). This enhanced fluorescence is likely a result of polarity‐dependent solvent effects; this interpretation is consistent with the gradual redshift of the emission spectra . Solvent polarity‐dependent fluorescence emission modulations have been reported .…”

Section: Methodssupporting

confidence: 86%

Crystallization‐Induced Emissive Invisible Ink

Zerby

Malka

Bhattacharya

et al. 2019

Advanced Optical Materials

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Section: Methodssupporting

confidence: 86%

Crystallization‐Induced Emissive Invisible Ink

Zerby

Malka

Bhattacharya

et al. 2019

Advanced Optical Materials

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“…In the excited state the maximum dipole moment (8.41 D) characterizes a conformer with one change in a torsion angle (C 1 -C 2 -C 3 -O 4 ) to 90°a nd the twist structure for both amino groups. The value of the dipole moment obtained, 8.41 D, is in complete agreement with our experimental estimation of the dipole moment of the excited state of MK (10.1 D [5]). …”

supporting

confidence: 88%

“…the bands for the transition to the first S pp state (340-355 nm [4]) for MK shows practically no effect of the medium. Hence it is impossible to explain all the variety of the spectral phenomena of MK, starting from Fig.…”

mentioning

confidence: 91%

“…The quantum yield and the position of the fluorescence bands depends on many factors: polarity of the medium, presence of traces of water, etc. MK does not fluoresce in such non-polar solvents as hexane and cyclohexane [4,5]. The increase in the polarity of the medium shifts the fluorescence bathochromic into 400-600 nm region which is accompanied with an increase in the intensity of the fluorescence.…”

mentioning

confidence: 94%

“…However it is known that MK can fluoresce [4,5]. The quantum yield and the position of the fluorescence bands depends on many factors: polarity of the medium, presence of traces of water, etc.…”

mentioning

confidence: 98%

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Conformational Mobility of 4,4′-Bisdimethyl-Aminobenzophenone in the Excited State

Shcherban¹,

Granchak

Сахно³

et al. 2005

Theor Exp Chem

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Quantum-chemical calculations on various conformational states of the molecule of Michler's ketone have been carried out by semi-empirical and non-empirical methods (HyperChem 7.0 suite of programs and Gaussian 98). The influence of solvation on the relative levels of different orbital types and on the spin states of the molecule has been examined. The possibility of the TICT process occurring in polar media, which may have an important effect on the spectral characteristics of Michler's ketone, has been investigated.Key words: Michler's ketone, the TICT process, solvation energy, the PM3 method.Benzophenone and its amino-derivatives are used in industry as additives in polymerization mixtures as photo-initiators of polymerization. One example of this class of chromophore is 4,4¢-bisdimethylaminobenzophenone (also known as Michler's ketone, (MK)):the reactivity and spectral characteristics of which have been the subjects of a number of experimental studies [1-6]. Interpretation of the results of these studies has been proposed in terms of the formation of several conformers in the ground state and structural relaxation of the molecule on excitation, or the creation on excitation of a TICT state (twisted intramolecular charge transfer, i.e., a twisted state with intramolecular charge transfer). Literature results [3] may also indicate the formation of complexes of MK with solvent molecules.The problem of determining the nature of the luminescence and establishing the nature of the effect of a solvent on it also exists for other conformationally mobile molecules containing amino groups. One method for solving this problem is to use quantum-chemical analysis of the spectral properties of the chromophores. In particular, the results of such calculations indicate that the TICT state arises in the chromophores. But there are papers (e.g., see [7]) in which calculations do not confirm that the TICT process occurs in excited molecules, which the experimenters attribute a highly polar structure. Similar calculations have not yet been carried out for MK. In this study we have carried out quantum-chemical calculations on the energetic parameters of MK, the results of which have been compared with spectral data. 1980040-5760/05/4103-0198

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Hydrazine functionalized probes for chromogenic and fluorescent ratiometric sensing of pH and F−: experimental and DFT studies

Chowdhury

Mondal

Roy

et al. 2017

Photochem Photobiol Sci

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Two novel hydrazine based sensors, BPPIH (N,N-bis(perfluorophenyl)isophthalohydrazide) and BPBIH (N,N-bis(perfluorobenzylidene)isophthalohydrazide), are presented here. BPPIH is found to be a highly sensitive pH sensor in the pH range 5.0 to 10.0 in a DMSO-water solvent mixture with a pK value of 9.22. Interesting optical responses have been observed for BPPIH in the above mentioned pH range. BPBIH on the other hand turns out to be a less effective pH sensor in the above mentioned pH range. The increase in fluorescence intensity at a lower pH for BPPIH was explained by using density functional theory. The ability of BPPIH to monitor the pH changes inside cancer cells is a useful application of the sensor as a functional material. In addition fluoride (F) selectivity studies of these two chemosensors have been performed and show that between them, BPBIH shows greater selectivity towards F. The interaction energy calculated from the DFT-D3 supports the experimental findings. The pH sensor (BPPIH) can be further interfaced with suitable circuitry interfaced with desired programming for ease of access and enhancement of practical applications.

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Influence of polarity of medium on fluorescence characteristics of alkylaminobenzophenones

Cited by 3 publications

References 5 publications

Crystallization‐Induced Emissive Invisible Ink

Crystallization‐Induced Emissive Invisible Ink

Conformational Mobility of 4,4′-Bisdimethyl-Aminobenzophenone in the Excited State

Hydrazine functionalized probes for chromogenic and fluorescent ratiometric sensing of pH and F−: experimental and DFT studies

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