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Novel Fluorophores and Their Applications
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Novel Fluorophores and Their Applications

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Photochemistry".

Deadline for manuscript submissions: closed (31 March 2023) | Viewed by 11139

Special Issue Editors

Prof. Dr. Grigory V. Zyryanov

E-Mail Website
Guest Editor
1. I.Ya. Postovsky Insititute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences (IOS UB RAS), 620137 Ekaterinburg, Russia
2. Department of Organic and Biomolecular Chemistry, Ural Federal University, 620062 Ekaterinburg, Russia
Interests: fluorophores; chemosensors; ligands; drug candidates; fluorescence; luminescent lanthanide complexes; luminescence
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Emily V. Nosova

E-Mail Website
Guest Editor
Department of Organic and Biomolecular Chemistry, Ural Federal University, 620062 Ekaterinburg, Russia
Interests: heterocycles; fluorophores; complexes; biologically active compounds; aggregation-induced emission; solvatochromism; pH sensors; ligands

Special Issue Information

Dear Colleagues,

Fluorescence (photoinduced luminescence) is one of the most fascinating properties of organic, inorganic and hybrid compounds, allowing them to be successfully applied as fluorophores of various kinds, chemosensors and probes, dyes and stains, components of OLEDs, OFETs and NLO and photovoltaic devices and so on. This Special Issue of Molecules is aimed at collecting review and research papers dealing with the preparation of novel fluorophores and their applications as fluorescent dyes and stains, chemosensors and probes and materials for molecular electronics/photovoltaics, as well as on theoretical and experimental studies on the fluorescence properties of various fluorophore systems aiming at better understanding fluorescence mechanisms and targeted fluorophore design. We welcome authors to submit their review, mini-review and research articles to this Special Issue.  

Prof. Dr. Grigory V. Zyryanov
Prof. Dr. Emily V. Nosova
Guest Editors

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Keywords

  • fluorophores and fluorescent dyes/stains
  • fluorescence (bio)imaging
  • fluorescence detection/quenching/enhancement
  • aggregation-induced emission
  • solvatochromism
  • NLO-fluorophores
  • local excitation
  • charge and energy transfer
  • DFT analysis of fluorescence processes

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Published Papers (5 papers)

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Research

13 pages, 2695 KiB  
Article
(1-(4-(5-Phenyl-1,3,4-oxadiazol-2-yl)phenyl)-1H-1,2,3-triazol-4-yl)-methylenyls α,ω-Bisfunctionalized 3- and 4-PEG: Synthesis and Photophysical Studies
by Mohammed S. Mohammed, Igor S. Kovalev, Natalya V. Slovesnova, Leila K. Sadieva, Vadim A. Platonov, Grigory A. Kim, Rammohan Aluru, Alexander S. Novikov, Olga S. Taniya and Valery N. Charushin
Molecules 2023, 28(13), 5256; https://doi.org/10.3390/molecules28135256 - 6 Jul 2023
Cited by 2 | Viewed by 1504
Abstract
Two new azaheterocycle-based bolas, such as (1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)-1H-1,2,3-triazol-4-yl)-methylenyls α,ω-bisfunctionalized PEGs, were prepared via Cu-catalyzed click reaction between 2-(4-azidophenyl)-5-(aryl)-oxadiazole-1,3,4 and terminal ethynyls derived from PEG-3 and PEG-4. Due to the presence of two heteroaromatic cores and a PEG linker, these bola molecules are [...] Read more.
Two new azaheterocycle-based bolas, such as (1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)-1H-1,2,3-triazol-4-yl)-methylenyls α,ω-bisfunctionalized PEGs, were prepared via Cu-catalyzed click reaction between 2-(4-azidophenyl)-5-(aryl)-oxadiazole-1,3,4 and terminal ethynyls derived from PEG-3 and PEG-4. Due to the presence of two heteroaromatic cores and a PEG linker, these bola molecules are considered as promising fluorescent chemosensors for electron-deficient species. As a result of a well-pronounced “turn-off” fluorescence response towards common nitro-explosive components, such as 2,4-dinitrotoluene (DNT) and 2,4,6-trinitrotoluene (TNT), hard-to-detect pentaerythritol tetranitrate (PETN), as well as Hg2+ cation was observed. Full article
(This article belongs to the Special Issue Novel Fluorophores and Their Applications)
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21 pages, 14262 KiB  
Article
New TEMPO–Appended 2,2′-Bipyridine-Based Eu(III), Tb(III), Gd(III) and Sm(III) Complexes: Synthesis, Photophysical Studies and Testing Photoluminescence-Based Bioimaging Abilities
by Nataliya V. Slovesnova, Artem S. Minin, Anna V. Belousova, Aleksey A. Ustyugov, Kirill D. Chaprov, Alexey P. Krinochkin, Maria I. Valieva, Yaroslav K. Shtaitz, Ekaterina S. Starnovskaya, Igor L. Nikonov, Anton N. Tsmokalyuk, Grigory A. Kim, Sougata Santra, Dmitry S. Kopchuk, Emiliya V. Nosova and Grigory V. Zyryanov
Molecules 2022, 27(23), 8414; https://doi.org/10.3390/molecules27238414 - 1 Dec 2022
Viewed by 1789
Abstract
Linked to Alzheimer’s disease (AD), amyloids and tau-protein are known to contain a large number of cysteine (Cys) residues. In addition, certain levels of some common biogenic thiols (cysteine (Cys), homocysteine (Hcy), glutathione (GSH), etc.) in biological fluids are closely related to [...] Read more.
Linked to Alzheimer’s disease (AD), amyloids and tau-protein are known to contain a large number of cysteine (Cys) residues. In addition, certain levels of some common biogenic thiols (cysteine (Cys), homocysteine (Hcy), glutathione (GSH), etc.) in biological fluids are closely related to AD as well as other diseases. Therefore, probes with a selective interaction with the above-mentioned thiols can be used for the monitoring and visualizing changes of (bio)thiols in the biological fluids as well as in the brain of animal models of Alzheimer’s disease. In this study, new Eu(III), Tb(III), Gd(III) and Sm(III) complexes of 2,2′-bipyridine ligands containing TEMPO fragments as receptor units for (bio)thiols are reported. The presence of free radical fragments of the ligand in the complexes was proved by using the electronic paramagnetic resonance (EPR) method. Among all the complexes, the Eu(III) complex turned out to be the most promising one as luminescence- and spin-probe for the detection of biogenic thiols. The EPR and fluorescent titration methods showed the interaction of the resulting complex with free Cys and GSH in solution. To study the practical applicability of the probes for the monitoring of AD in-vivo, by using the above-mentioned Eu(III)-based probe, the staining of the brain of mice with amyloidosis and Vero cell cultures supplemented with the cysteine-enriched medium was studied as well as the fluorescence titration of Bovine Serum Albumin, BSA (as the model for the thiol moieties containing protein), was carried out. Based on the results of fluorescence titration, the formation of a non-covalent inclusion complex between the above-mentioned Eu(III) complex and BSA was suggested. Full article
(This article belongs to the Special Issue Novel Fluorophores and Their Applications)
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15 pages, 4886 KiB  
Article
Synthesis and Photophysical Properties of α-(N-Biphenyl)-Substituted 2,2′-Bipyridine-Based Push–Pull Fluorophores
by Ekaterina S. Starnovskaya, Dmitry S. Kopchuk, Albert F. Khasanov, Olga S. Taniya, Igor L. Nikonov, Maria I. Valieva, Dmitry E. Pavlyuk, Alexander S. Novikov, Grigory V. Zyryanov and Oleg N. Chupakhin
Molecules 2022, 27(20), 6879; https://doi.org/10.3390/molecules27206879 - 13 Oct 2022
Cited by 8 | Viewed by 1815
Abstract
A series of new α-(N-biphenyl)-substituted 2,2′-bipyridines were obtained through the combination of the ipso-nucleophilic aromatic substitution of the C5-cyano group, aza-Diels–Alder and Suzuki cross-coupling reactions, starting from 5-cyano-1,2,4-triazines. For the obtained compounds, photophysical and fluorosolvatochromic properties were studied. Fluorophores 3l and [...] Read more.
A series of new α-(N-biphenyl)-substituted 2,2′-bipyridines were obtained through the combination of the ipso-nucleophilic aromatic substitution of the C5-cyano group, aza-Diels–Alder and Suzuki cross-coupling reactions, starting from 5-cyano-1,2,4-triazines. For the obtained compounds, photophysical and fluorosolvatochromic properties were studied. Fluorophores 3l and 3b demonstrated unexpected AIEE activity, while 3a and 3h showed promising nitroexplosive detection abilities. Full article
(This article belongs to the Special Issue Novel Fluorophores and Their Applications)
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Figure 1

16 pages, 11461 KiB  
Article
Push–Pull Derivatives Based on 2,4′-Biphenylene Linker with Quinoxaline, [1,2,5]Oxadiazolo[3,4-B]Pyrazine and [1,2,5]Thiadiazolo[3,4-B]Pyrazine Electron Withdrawing Parts
by Egor V. Verbitskiy, Pascal le Poul, Filip Bureš, Sylvain Achelle, Alberto Barsella, Yuriy A. Kvashnin, Gennady L. Rusinov and Valery N. Charushin
Molecules 2022, 27(13), 4250; https://doi.org/10.3390/molecules27134250 - 30 Jun 2022
Cited by 18 | Viewed by 2455
Abstract
A series of novel V-shaped quinoxaline, [1,2,5]oxadiazolo[3,4-b]pyrazine and [1,2,5]thiadiazolo[3,4-b]pyrazine push–pull derivatives with 2,4′-biphenylene linker were designed and their electrochemical, photophysical and nonlinear optical properties were investigated. [1,2,5]Oxadiazolo[3,4-b]pyrazine is the stronger electron-withdrawing fragment as shown by electrochemical, and [...] Read more.
A series of novel V-shaped quinoxaline, [1,2,5]oxadiazolo[3,4-b]pyrazine and [1,2,5]thiadiazolo[3,4-b]pyrazine push–pull derivatives with 2,4′-biphenylene linker were designed and their electrochemical, photophysical and nonlinear optical properties were investigated. [1,2,5]Oxadiazolo[3,4-b]pyrazine is the stronger electron-withdrawing fragment as shown by electrochemical, and photophysical data. All compounds are emissive in a solid-state (from the cyan to red region of the spectrum) and quinoxaline derivatives are emissions in DCM solution. It has been found that quinoxaline derivatives demonstrate important solvatochromism and extra-large Stokes shifts, characteristic of twisted intramolecular charge transfer excited state as well as aggregation induced emission. The experimental conclusions have been justified by theoretical (TD-)DFT calculations. Full article
(This article belongs to the Special Issue Novel Fluorophores and Their Applications)
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19 pages, 4169 KiB  
Article
Amphipolar, Amphiphilic 2,4-diarylpyrano[2,3-b]indoles as Turn-ON Luminophores in Acidic and Basic Media
by Tobias Wilcke, Alexandru Postole, Marcel Krüsmann, Matthias Karg and Thomas J. J. Müller
Molecules 2022, 27(7), 2354; https://doi.org/10.3390/molecules27072354 - 6 Apr 2022
Cited by 1 | Viewed by 2380
Abstract
A versatile amphiphilic pyrano[2,3-b]indole for halochromic turn-ON luminescence in acidic or basic media is accessed by an insertion-coupling-cycloisomerization and adjusting solubilizing and phenolic functionalities. While almost non-emissive in neutral solutions, treatment with acids or bases like trifluoroacetic acid (TFA) or 1,8-diazabicyclo[5.4.0]undec-7-ene [...] Read more.
A versatile amphiphilic pyrano[2,3-b]indole for halochromic turn-ON luminescence in acidic or basic media is accessed by an insertion-coupling-cycloisomerization and adjusting solubilizing and phenolic functionalities. While almost non-emissive in neutral solutions, treatment with acids or bases like trifluoroacetic acid (TFA) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) reveals distinct luminescence at wavelengths of 540 nm or 630 nm in propan-2-ol, respectively. Turn-ON emission can be detected at pH values as mild as pH = 5.31 or 8.70. Quantum yields in propan-2-ol are substantial for protonated (Φf = 0.058) and deprotonated (Φf = 0.059) species. Photometrically, pKa1 of 3.5 and pKa2 of 10.5 were determined in propan-2-ol. With lipophilic polyether sidechains and hydrophilic protonation and deprotonation sites the molecule can be regarded as amphipolar, which results in good solubility properties for different organic solvents. In aqueous media, an organic co-solvent like propan-2-ol (35%) or tetrahydrofuran (25%) is needed, and the solution can be diluted with pure water without precipitation of the compound. At higher concentrations of water, a turbid solution is formed, which indicates the formation of micellar structures or clusters. With dynamic light scattering we could show that these clusters increase in size with increasing water content. Full article
(This article belongs to the Special Issue Novel Fluorophores and Their Applications)
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