Spectral properties and dynamics of the excited state structural relaxation of the ortho analogues of POPOP — Effective abnormally large Stokes shift luminophores

Дорошенко, А. О.; Kirichenko, Alexander; Mitina, V. G.; Ponomaryov, O. A.

doi:10.1016/1010-6030(95)04203-2

Cited by 61 publications

(17 citation statements)

References 15 publications

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“…42,43 Briefly, fluorescence decay curves were recorded every 10 nm in the UV-vis region (370-700 nm) to cover the whole fluorescence decay surface. The data were processed using a procedure incorporated in the Spectral Data Lab software 44 kindly provided by Prof. A.O.…”

Section: Synthesesmentioning

confidence: 99%

Origin of Spectral Features and Acid–Base Properties of 3,7-Dihydroxyflavone and Its Monofunctional Derivatives in the Ground and Excited States

2016

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Comprehensive spectral investigations of 3,7-dihydroxyflavone and its two derivatives, which each contain a methyl-blocked hydroxyl group, reveal complex radiation absorption in the 300-450 nm range and emission in the 370-650 nm range. The absorption and fluorescence characteristics of these compounds depend on the pH/H0 of the water/methanol media, which is caused by the existence of the compounds in various protolytic (cationic, neutral, anionic) and tautomeric forms. Combined analysis of steady-state, time-dependent and fluorescence decay spectral data enabled the identification of the emitting species, determination of their lifetimes with respect to radiative and nonradiative deactivation processes, fluorescence quantum yields, protolytic and tautomeric abilities under various conditions, and acidic dissociation constants of the cationic, neutral, and anionic forms of the compounds. Results of calculations carried out at the DFT and TD DFT levels of theory generally confirmed the experimental findings concerning tautomeric/protolytic transformations and equilibria. Computational methods also provided insight into possible tautomerization pathways. Electronically excited molecules are generally much more susceptible to tautomerization and acidic dissociation than ground-state ones. 3,7-Dihydroxyflavone exhibits distinguishable features among the compounds investigated and can be considered as potential spectral indicator of properties (polarity, hydrophobicity, hydrogen-bonding ability) and acidity/basicity of liquid environments.

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Section: Synthesesmentioning

confidence: 99%

Origin of Spectral Features and Acid–Base Properties of 3,7-Dihydroxyflavone and Its Monofunctional Derivatives in the Ground and Excited States

2016

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“…Generally, enlarged fluorescence Stokes shifts are typical to 1,3,5-triphenyl-substituted pyrazolines and pyrazoles (see section 3.2). Definite excited state structural relaxation processes could be among the reasons of such behavior, which make the initially unplanar unexcited molecule more planar and more conjugated in its fluorescent S 1 -state [56][57][58][59]. This results in additional decrease of the energy of structurally relaxed excited state and corresponding Stokes shift enlargement.…”

Section: Methodsmentioning

confidence: 99%

1,5-Diaryl-3-Benzimidazolyl-2-Pyrazolines and Pyrazoles – Novel Fluorescent Dyes of Pyrazoline Family

Kotlyar¹,

Orlov²,

Grygorovych³

et al. 2017

Chemical Series

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A series of novel aryl derivatives of 2-pyrazoline bearing 2-benzimidazolyl moiety was synthesized via condensation of corresponding chalcones with phenyl hydrazine. Pyrazoles on their background were obtained by the optimized oxidation procedure with manganese dioxide in benzene. Fluorescent characteristics of the title compounds were determined for their solutions in acetonitrile. Quantum-chemical modeling of molecular structure, UV/Vis spectra, electron density redistribution and structural relaxation at electronic excitation resulting in high fluorescence Stokes shifts were conducted as well.

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“…Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 (Doroshenko, 1996(Doroshenko, , 1999(Doroshenko, , 2000b. These molecules are prospective for their practical application as fluorescent probes, labels and chemosensors (Doroshenko, 2002a).…”

Section: Methodsmentioning

confidence: 99%

“…Presence of two bulky heterocyclic substituents in 1,2-positions of the ortho-POPOP central benzene ring results in a significant sterical hindrance. This hindrance is manifested by a prominent non-planarity of ortho-POPOPs both in the crystalline state (Doroshenko, 1994) and in solutions (Doroshenko, 1996(Doroshenko, , 2002a. All the already examined crystal structures of the ortho-analogs of POPOP are characterized by essentially different angles between the planes of the central phenylene and each of the attached heterocyclic rings.…”

Section: Methodsmentioning

confidence: 99%

“…For background to the practical applications of 1,2-bis-(5phenyl-oxazol-2-yl)benzene (ortho-POPOP) analogs (spectroscopic and fluorescence kinetics data), see: Doroshenko et al (1996Doroshenko et al ( , 1999Doroshenko et al ( , 2000aDoroshenko et al ( ,c, 2002a, Kirichenko et al (1998). For related structures, see: Doroshenko et al (1994Doroshenko et al ( , 1997Doroshenko et al ( , 2000bDoroshenko et al ( , 2002b.…”

Section: Related Literaturementioning

confidence: 99%

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5-(4-Fluorophenyl)-2-[2-(5-phenyl-1,3-oxazol-2-yl)phenyl]-1,3-oxazole

et al. 2010

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In the title compound, C24H15FN2O2, the dihedral angles between the central benzene ring and the oxazole rings are 10.7 (6) and 64.1 (5)°. The dihedral angles between the oxazole rings and their pendant rings are 2.0 (3) and 24.3 (2)°. The F atoms are disordered over two sites with occupancies of 0.627 (3) and 0.373 (3) in the phenylene–oxazolyl–phenyl and in oxazolyl–phenyl fragments, respectively. In the crystal structure, molecules are linked through a network of C—H⋯F and weak π–π stacking interactions.

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Spectral properties and dynamics of the excited state structural relaxation of the ortho analogues of POPOP — Effective abnormally large Stokes shift luminophores

Cited by 61 publications

References 15 publications

Origin of Spectral Features and Acid–Base Properties of 3,7-Dihydroxyflavone and Its Monofunctional Derivatives in the Ground and Excited States

Origin of Spectral Features and Acid–Base Properties of 3,7-Dihydroxyflavone and Its Monofunctional Derivatives in the Ground and Excited States

1,5-Diaryl-3-Benzimidazolyl-2-Pyrazolines and Pyrazoles – Novel Fluorescent Dyes of Pyrazoline Family

5-(4-Fluorophenyl)-2-[2-(5-phenyl-1,3-oxazol-2-yl)phenyl]-1,3-oxazole

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