Laboratory "Chemistry and molecular photonics of dipyrromethene dyes and luminophores"

Research department: Development of physical chemistry approaches and methods in the study of multicomponent supramolecular, molecular and ion-molecular systems as promising materials

Scientific trac: Chemistry and molecular photonics of dipyrromethene luminophores.

The scientific track includes developments in the field of synthesis, experimental and theoretical studies of the physicochemical properties of dyes and luminophores based on ligands and coordination compounds of dipyrromethenes with p- and d-elements in condensed media.

Particular attention is paid to the study of the influence of structural and solvation effects, supramolecular complex formation on the spectral and luminescent characteristics of dipyrromethene compounds, as well as the search for multifunctional chromophores and fluorescent markers, sensors (for ions, low and high molecular weight compounds), and the development of protocols for their implementation in the fields of bioimaging, fluorescent sensing, proteomics, diagnostics, photodynamic therapy, including antibacterial applications, and theranostics.

The main directions of group members' scientific activities include

  • Molecular design of luminophores based on dipyrromethenes and related structures

       Dr. of Chemical Science, Prof., Chief Researcher Berezin Mikhail Borisovich

The relationship between molecular design and the practical properties of synthetic analogs of bilin pigments, which are products of natural porphyrin catabolism, is under study. New methods for synthesizing ligands of dipyrromethenes, bisdipyrromethenes, and their coordination compounds with p- and d-elements, including BF2-dipyrromethenes (BODIPY), are being developed as they are considered the most promising and versatile among known luminophores classes.

Methodological aspects of the rational synthesis of symmetrically and asymmetrically substituted dipyrromethene luminophores with two or more chromophoric BODIPY domains are being explored. The study includes investigations into structural isomerism, significant spectral characteristics, photo- and thermal stability parameters of oligo-derivatives of BODIPY ligands and their complexes. These parameters depend on the nature of substituents in the pyrrole rings and meso-spacers, including aryl, alkyl, carboxy, thio, amino-alkyl, and halogen atoms.

  • Control of aggregation and photophysical functions of BODIPY luminophores in solutions and thin films

       Candidate of Chemical Science, Senior Researcher Antina Lyubov Anatolevna

In thin films, at the interface surface, in water, and in binary water-organic mixtures, we observe intense aggregation of hydrophobic BODIPY luminophores, leading to dramatic changes in their spectral properties compared to dilute solutions in organic solvents. To enhance the efficiency of using BODIPY dyes in biomedicine, optics, and electronics, we are developing methods to control BODIPY aggregation in aqueous-organic mixtures, polymer composites, and Langmuir-Schaeffer thin films through targeted functionalization of the molecular structure of the luminophores.

  • Non-covalent supramolecular systems based on BODIPY and single-walled carbon nanotubes (SWCNTs)

        Candidate of Chemical Sciences, Senior Researcher Antina Lyubov Anatolevna

Non-covalent supramolecular systems based on BODIPY and single-walled carbon nanotubes (SWCNTs) with an absorption/emission range extended from the UV to the IR region have been obtained. Systems of this kind are of particular interest as laser radiation limiters, components of organic shutters, frequency-tunable lasers operating in the near visible and IR regions of the spectrum, etc.

  • Nanostructured delivery systems for theranostics BODIPY for fluorescence diagnostics and photodynamic therapy

        Candidate of Chemical Sciences, Senior Researcher Antina Lyubov Anatolevna                 

        Candidate of Chemical Sciences, Junior Researcher Kalyagin Aleksandr Alekseevich

One of the primary challenges associated with the use of most BODIPY dyes in biomedicine is their high hydrophobicity. To address this issue, nanosized carriers and delivery systems for BODIPY luminophores are being developed. The encapsulation of BODIPY dyes into micelles of the biocompatible amphiphilic block copolymer Pluronic® F127 and into organometallic coordination polymers (e.g., Zif-8) is employed to create nanostructured systems with an optimal combination of spectral characteristics in aqueous and physiological environments. These materials are currently under testing as theranostics for fluorescent diagnostics, anticancer treatment, and antimicrobial photodynamic therapy.

  • Fluorescent sensors based on zinc(II) bis(dipyrromethenate)s for medical diagnostics

       Candidate of Chemical Sciences, Senior Researcher Ksenofontov Alexander Andreevich

Successful solution of modern problems of fluorescence sensing in various fields of science and technology, including environmental and medical-analytical monitoring, requires the creation of new highly sensitive, selective and cost-effective express methods for detecting in vitro and in vivo in solutions and gas mixtures of micro- and ultra-microquantities of toxic and biologically significant analytes, including aromatic organic compounds, amines, alcohols, diuretics, steroids, amino acids, etc.

New promising multifunctional fluorescent sensors based on zinc(II) coordination compounds with tetradentate bis(dipyrromethene) ligands (H2L) have been developed.

The mechanism of the spectral response of the sensors has been established, based on the effect of quenching their fluorescence due to supramolecular complex formation with molecules of analytes of various natures.

It is shown that the results obtained can be translated into the practical plane of such promising areas as:

  1. fluorescent detection of N-, O-electron-donor and aromatic compounds in organic media and gas mixtures;
  2. fluorescent determination of loop diuretics in organic and physiological fluids;
  3. development of photovoltaic systems based on zinc(II) bis(dipyrromethenate)s with C60 and C70 fullerenes.

  • Fluorescent probes for marking hydrophobic and hydrophilic zones of blood transport proteins

        Candidate of Chemical Sciences, Senior Researcher Ksenofontov Alexander Andreevich

Fluorescent probes based on BODIPY have been obtained for visualization of blood transport proteins.

  • Two-channel conjugates based on BODIPY and other types of dyes

       Candidate of Chemical Sciences, Senior Researcher Ksenofontov Alexander Andreevich

Two-channel conjugates of BODIPY with other types of dyes, capable of absorbing and emitting light simultaneously in several regions of the spectrum, have been obtained. These features provide more comprehensive information about biological objects and processes and are also important for multiplexing — the simultaneous detection of several analytes in a sample and the complex monitoring of multiple biomolecular interactions. Additionally, some of the synthesized conjugates can serve as theranostics. For example, BODIPY conjugates with cyanine dyes are characterized by simultaneous absorption and fluorescence in the green and red regions of the spectrum, as well as antibacterial activity.

  • Development of a new class of chromofluorogenic sensors of biologically active and toxic metal ions based on dipyrromethene chelate ligands

       Candidate of Chemical Sciences, Researcher Bumagina Natalya Anatolyevna

The estimation of heavy metal ion content is one of the most crucial tasks in biochemistry, ecology, and various industries. Addressing this challenge involves the development of effective sensors and reliable methods for the rapid detection of trace amounts of metal ions. Using mono- and bis(dipyrromethene)s, we are actively working on the development of new selective chemosensors for colorimetric and fluorescent determination of metal ions in both organic and aqueous media. We study how the molecular structure of these chemosensors influences the selectivity and sensitivity of analyte detection through comprehensive theoretical and experimental investigations of the thermodynamics and spectral responses of complexation reactions between chromophore ligands and metal cations. We are also developing methods for the qualitative and quantitative determination of cations in solutions, including rapid analysis, spectrofluorimetric techniques, and extraction-spectrophotometric approaches. We substantiate the practical applicability of dipyrromethene sensors for analyzing metal cations in natural and waste waters as well as biorelevant media.

  • BODIPY biomarkers and theranostics for fluorescence diagnostics and photodynamic therapy

       Candidate of Chemical Sciences, Senior Researcher Guseva Galina Borisovna

In the context of biochemistry and biomedicine, we are actively developing new multifunctional fluorescent boron(III)dipyrromethene dyes (BODIPY). These dyes are designed to have an optimal combination of fluorescence characteristics, photo- and pH-stability, as well as an affinity for cellular organelles, hydrophobic and hydrophilic compounds, and biological media. Our research focuses on identifying BODIPY dyes that can easily penetrate cell membrane lipid layers and selectively stain microbial cell organelles, including Gram-positive and Gram-negative bacteria and pathogenic fungi.

Additionally, our exploratory research extends to the development of effective theranostics using BODIPY conjugates with monoterpenoids and other medicinal compounds. We are actively addressing the challenge of structural modification to achieve optimal fluorescence and singlet oxygen generation indicators, biocompatibility (cytotoxicity), and the treatment of infections caused by antibiotic-resistant strains of microorganisms. These endeavors involve the utilization of fluorescent diagnostics and antimicrobial photodynamic therapy.

  • New photosensitizers based on halogen-substituted dipyrromethates of d- and p-elements for photodynamic antibacterial and anticancer therapy

            Candidate of Chemical Sciences, Researcher Lapshina Ekaterina Nailovna                                           Candidate of Chemical Sciences, Senior Researcher Guseva Galina Borisovna

Dipyrromethene dyes containing 'heavy' bromine or iodine atoms in their structure offer a significant advantage in the effective generation of singlet oxygen (1O2), making them promising sensitizers for photodynamic antibacterial and anticancer therapy. To harness this potential, we are developing molecular design strategies aimed at obtaining halogen-substituted dipyrromethates of d- and p-elements that combine effective 1O2 generation and other reactive oxygen species with high photostability and low cytotoxicity.

Our research includes comprehensive studies on the influence of molecular structural features and medium properties on the spectral and luminescent characteristics, singlet oxygen generation efficiency, photostability, lipophilicity, and pH stability of iodine- and bromine-substituted boron(III) and zinc(II) dipyrromethates. Additionally, in collaboration with colleagues from Kazan Federal University, we are investigating cytotoxicity, permeability through cell lipid layers, and photodynamic activity.

 

Projects and grants:
  • РНФ 23-23-00206, «Тераностические агенты на основе бор(III)дипиррометеновых димеров и мицеллярные системы их целевой доставки для ранней диагностики и лечения раковых заболеваний».
  • 075-15-2021-579, Компьютерный синтез химических соединений с заданными свойствами ("Мегагрант").
  • РФФИ 20-43-370011, Разработка водорастворимых 3D-архитектур на основе металлоорганических каркасов (MOК) для точечной доставки бор(III)дипиррометеновых (BODIPY) люминесцентных маркеров, зондов и агентов фотодинамической терапии. 2020 – 2023 г.г.
  • РНФ 20-63-47-026, Новые подходы к снижению устойчивости микроорганизмов к антибиотикам при смешанных инфекциях: поиск новых антимикробных субстанций на основе полусинтетических тиотерпеноидов, характеристика молекулярных мишеней и механизмов действия, разработка эффективной системы доставки антимикробных агентов и ее визуализация с помощью конъюгатов с BODIPY-люминофорами. 2020 – 2023 г.г.
  • МК-197.2021.1.3, Разработка новых флуоресцентных зондов гидрофобных областей глобулярных белков на основе структурно-модифицированных бор(III)дипиррометенатов (BODIPY).2021 – 2022 г.
  • РФФИ 19-33-60052, Новые фотосенсибилизаторы на основе галогензамещенных дипиррометенатов бора(III) и цинка(II) для фотодинамической инактивации микроорганизмов: развитие фундаментальных основ и аспектов практического применения. 2019 – 2022 г.г.
  • РФФИ 19-33-90115, Новые флуоресцентные сенсоры кислородсодержащих соединений на основе bis (BODIPY) люминофоров. 2019 – 2021 г.г.
  • РФФИ 18-29-04016, Железосодержащие самоорганизующиеся координационные полимеры для материалов нового поколения с термо- и фотоуправляемыми магнитными свойствами. 2018 – 2021г
  • РФФИ_мк 18-29-06008, Влияние сверхкритического растворителя на полиморфизм нанокристаллических форм биологически активных соединений в полимерной матрице. 2018-2021
  • 18-33-20218 мол_а_вед, Бордипиррины и бис(дипирринаты) цинка как флуоресцентные сенсоры на стероидные гормоны. 2018 – 2020 г.г.
  • 18-33-00031 мол_а, Новые флуоресцентные сенсоры на основе бис(дипиррометенатов) цинка(II) для детектирования диуретиков и их метаболитов в физиологических жидкостях. 2018 – 2019 г.г.
  • 16-33-00582 мол_а, Новые флуоресцентные хемосенсоры на основе бис(дипирринатов) цинка(II) для детектирования бензола, толуола и ксилолов в воздухе и жидких средах.
  • РФФИ 16-33-00611 мол_а, Функциональная модификация BODIPY красителей для направленного регулирования характеристик их спектрально-люминесцентных, генерационных, термических и фотохимических свойств в растворах и твердой фазе. 2016–2017 г.г.
  • 15-43-03081 р_центр_а, Новые высокочувствительные хемосенсоры на основе бис(дипирринатов) цинка(II) для флуоресцентного анализа токсичных аминов и кислородсодержащих аналитов. 2015–2017 г.г.
Antina Elena Vladimirovna
Head of Laboratory
Doctor of сhemical sciences
professor
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Antina Lyubov Anatolyevna
Senior Researcher
Phd in chemistry
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Berezin Mikhail Borisovich
Chief Researcher
Doctor of сhemical sciences
professor
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Bocharov Pavel Sergeevich
Intern Researcher
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Bumagina Natalya Anatolyevna
Researcher
Phd in chemistry
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Guseva Galina Borisovna
Senior Researcher
Phd in chemistry
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Kalyagin Aleksandr Alekseevich
Junior Researcher
Phd in chemistry
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Ksenofontov Alexander Andreevich
Senior Researcher
Phd in chemistry
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Lapshina Ekaterina Nailovna
Researcher
Phd in chemistry
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Vyugin Anatoly Ivanovich
Chief Researcher
Doctor of сhemical sciences
professor
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Обзоры:

  1. Antina  E.V., Kuznetsova R.T., Antina L.A., Guseva G.B., Dudina N.A., V'yugin A.I., Solomonov A.V.  New luminophors based on the binuclear helicates of d-METALS with BIS(DIPYRRIN)S  // Dyes and Pigments. ‒ 2015. ‒ V. 113, № 20. – P. 664–674.
  2. Antina E.V., Bumagina N.A. Tetraaryl-substituted aza-BODIPY: synthesis, spectral properties, and possible applications (microreview)  // Chemistry of Heterocyclic Compounds. ‒ 2017. ‒ V. 53, №  1. – P. 39–41.
  3. Antina E.V., Bumagina N.A., V'yugin A.I., Solomonov A.V. Fluorescent indicators of metal ions based on dipyrrоmethene platform  // Dyes and Pigments. ‒ 2017. ‒ V. 136, № 17. – P. 368–381.
  4. Antina E.V., Bumagina N.A, Berezin M.B.  Bis(dipyrromethene)s as a new class of highly efficient chromo-fluorogenic ligands  // Dyes and Pigments. ‒ 2021. ‒ V. 195. – Art. 109656.
  5. Antina E.V., Berezin M.B., V’yugin A.I., Guseva G.B., Bumagina N.A., Antina L.A., Ksenofontov A.A., Nuraneeva E.N., Kalyagin A.A., Bocharov P.S. , Lukanov M.M., Krasovskaya Z.S., Kalinkina V.A., Dogadaeva S.A. Chemistry and Practical Application of Dipyrromethene Ligands, Salts, and Coordination Compounds as Optical Sensors for Analytes of Various Nature (A Review) // Russian Journal of Inorganic Chemistry. ‒ 2022. ‒ V. 67, № 3. – P. 321–337.
  6. Antina E., Bumagina N., Marfin Y., Guseva G., Nikitina L., Sbytov D., Telegin F. BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment // Molecules. ‒ 2022. ‒ V. 27, № 4. – P. 1396.
  7. Bumagina N.A., Antina E.V., Ksenofontov A.A., Antina L.A., Kalyagin A.A., Berezin M.B. Basic structural modifications for improving the practical properties of BODIPY  // Coordination Chemistry Reviews. ‒ 2022. ‒ V. 469, № 4. – Art. 214684.

Статьи:

  1. Bumagina N.A., Antina E.V., Berezin M.B., Kalyagin A.A. Influence of structural and solvation factors on the spectral-fluorescent properties of alkyl-substituted BODIPYs in solutions  // Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. ‒ 2017. ‒ V. 173. –  P. 228–234.
  2. Bumagina N.A., Antina E.V., Sozonov D.I. Off-on fluorescent sensor based on the bis(2,4,7,8,9-pentamethyldipyrrolylmethene-3-yl)methane for detection of Cd 2+ and Hg 2+ cations  // Journal of Luminescence. ‒ 2017. ‒ V. 183. – P. 315–321.
  3. Ksenofontov A.A., Guseva G.B., Antina E.V., Nuraneeva E.N «Оn-off» fluorescent sensors for aromatic analytes based on zinc(II) bis(dipyrromethenate)s // Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. ‒ 2017. ‒ V. 173. – P. 222–227.
  4. Ksenofontov A.A., Guseva G.B., Antinа E.V., Khodov I.A., Vyugin A.I. Zinc(II) bis(dipyrromethenate)s crystal solvates with dimethyl sulfoxide Composition, stability and spectral-luminescent properties // Sensors and Actuators B: Chemical. ‒ 2017. ‒ V. 251. – P. 858–868.
  5. Bumagina N.A., Kritskaya A.Y., Antina E.V., Berezin M.B., V’yugin A.I. Effect of Alkyl, Aryl, and meso-Aza Substitution on the Thermal Stability of BODIPY  // Russian Journal of Inorganic Chemistry. ‒ 2018. ‒ V. 63, № 10. – P. 1326–1332.
  6. Nuraneeva E.N., Antina E.A., Guseva G.B., Berezin M.B., V'yugin A.I.   Effects of halogen substitution on the photostability and thermal degradation of boron(III), zinc(II) and cadmium(II) dipyrrinato complexes // Inorganica Chimica Acta. ‒ 2018. ‒ V. 482. – P. 800–806.
  7. Kritskaya A.Y., Bumagina N.A, Antina E.V., Ksenofontov A.A., Berezin M.B., Semeikin A.S. Synthesis and Photochemical Properties of 2,3;5,6-bis(cyclohexano)-BODIPY . // Journal of fluorescence. ‒ 2018. ‒ V. 28, №.1. – P. 393–407.
  8. Antina L.A., Ksenofontov A.A., Kalyagin A.A., Antina E.V., Berezin M.B., Khodov I.A. Luminescent properties of new 2,2-, 2,3- and 3,3-CH2-bis(BODIPY)s dyes: Structural and solvation effects // Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. ‒ 2019. ‒ V. 218. – P. 308–319.
  9. Ksenofontov A.A., Antina E.V., Guseva G.B., Berezin M.B., Antina L.A., Vyugin A.I.Prospects of applications of fluorescent sensors based on zinc(II) and boron(III) bis(dipyrromethenate)s  // Journal of Molecular Liquids. ‒ 2019. ‒ V. 274. – P. 681–689.
  10. Ksenofontov A.A., Bocharov P.S., Antina E.V. Interaction of tetramethyl-substituted BODIPY dye with bovine serum albumin: Spectroscopic study and molecular docking // Journal of Photochemistry and Photobiology A: Chemistry. ‒ 2019. ‒ V. 368. – P. 254–257.
  11. Ksenofontov A.A., Stupikova S.A., Bocharov P.S.,. Lukanov M.M, Ksenofontova K.V., Khodov I.A., Antina E.V. Novel fluorescent sensors based on zinc(II) bis(dipyrromethenate)s for furosemide detection in organic media // Journal of Photochemistry and Photobiology A: Chemistry. ‒ 2019. ‒ V. 382. – Art. 111899.
  12. Kuznetsova R.T., Aksenova I.V., Prokopenko A.A., Pomogaev V.A., Antina E.V., Berezin M.B., Antina L.A., Bumagina N.A. Photonics of boron(III) and zinc(II) dipyrromethenates as active media for modern optical devices // Journal of Molecular Liquids. ‒ 2019. ‒ V. 278. – P. 5–11.
  13. Antina L.A., Ksenofontov A.A., Kalyagin A.A., Bocharov P.S., Kharitonova N.V., Kazak A.V., Antina E.V., Berezin M.B.  The influence of alkylation on the photophysical properties of BODIPYs and their labeling in blood plasma proteins  // Journal of Molecular Liquids. ‒ 2020. ‒ V. 304. – Art. 112717.
  14. Ksenofontov A.A., Lukanov M.M., Antina E.V. Fluorescent detection of loop diuretics by sensors based on zinc(II) bis(dipyrromethenate)s  // Dyes and Pigments. ‒ 2020. ‒ V. 179. – Art. 108389.
  15. Nuraneeva E.N., Guseva G.B., Antinа E.V., V'yugin A.I.Influence of structural factors and medium properties on the fluorescence of alkyl and halogen substituted zinc(II) dipyrromethenates // Journal of Molecular Liquids. ‒ 2020. ‒ V. 298, № 5. – Art. 112026.
  16. Antina L.A., Berezin M.B.  Effect of polar protic solvents on the photophysical properties of bis(BODIPY) dyes // Journal of Molecular Liquids. ‒ 2021. ‒ V. 337. – Art. 116416.
  17. Antina L.A., Ksenofontov A.A., Kazak A.V., Usol’tseva N.V., Antina E.V., Berezin M.B.  Effect of ms-substitution on aggregation behavior and spectroscopic properties of BODIPY dyes in aqueous solution, Langmuir-Schaefer and poly(methyl methacrylate) thin films // Colloids and Surfaces A: Physicochemical and Engineering Aspects. ‒ 2021. ‒ V. 618. – Art. 126449.
  18. Ksenofontov A.A., Lukanov M.M., Bichan N.G., Khodov I.A., Kudryakova N.O., Ksenofontova K.V., Antina E.V. Non-covalent supramolecular systems with photoinduced electron transfer based on zinc bis(dipyrromethenate)s and C60  // Dyes and Pigments. ‒ 2021. ‒ V. 185, № 29. – Art. 108918.
  19. Nuraneeva E.N., Guseva G.B., Antina E.V. Formation and thermal stability of supramolecular complexes of dibromosubstituted zinc(II) dipyrromethenate with ethanol and N,N – dimethylformamide // Thermochimica Acta. ‒ 2021. ‒ V. 699. – Art. 178911.
  20. Nuraneeva E.N., Guseva G.B., Antina E.V.  A New «off-on» Fluorescence Zinc Ion Sensors Based on Iodo- and Bromosubstituted Dipyrromethenes  // Journal of fluorescence. ‒ 2021. ‒ l. 31, iss. 2. – P. 415–425.
  21. Antina L.A., Bumagina N.A., Kalinkina V.A., Lukanov M.M., Ksenofontov A.A., Kazak A.V., Berezin M.B., Antina E.V. Aggregation behavior and spectroscopic properties of red-emitting distyryl-BODIPY in aqueous solution, Langmuir-Schaefer films and Pluoronic® F127 micelles  // Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. ‒ 2022. ‒ V. 278. – Art. 121366.
  22. Antina L.A., Kalyagin A.A., Ksenofontov A.A., Pavelye R.S., Lodochnikova O.A., Islamov D.R., Berezin M.B., Antina E.V. Effects of ms-aryl substitution on the structure and spectral properties of new CH(Ar)-bis(BODIPY) luminophores  // Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. ‒ 2022. ‒ V. 265. – Art. 120393.
  23. Berezin M.B., Dogadaeva S.A., Antina E.V., Lukanov M.M., Ksenofontov A.A., Semeikin A.A. Design and physico-chemical properties of unsymmetrically substituted dipyrromethenes and their complexes with boron(III) and zinc(II)  // Dyes and Pigments. ‒ 2022. ‒ V. 202. – Art. 110215.
  24. Bumagina N.A., Antina E.V., Krasovskaya Z.S., Berezin M.B., Ksenofontov A.A. , Vyugin A.I., Semeikin A.S. Dipyrromethene chromo-fluorogenic chemosensors for quantitative detection and express analysis of Zn2+ ions /  // Journal of Molecular Liquids. ‒ 2022. ‒ V. 345, № 4. – Art. 117834.
  25. Guseva G.B., Antina E.V., Berezin M.B., Ksenofontov A.A., Bocharov P.S., Smirnova A.S., Pavelyev R.S., Gilfanov I.R., Pestova S.V. , Izmest'ev E.S., Rubtsova S.A., Kayumov A.R., Kiselev S.V., Azizova Z.R., Ostolopovskaya O.V., Efimov S.V., Klochkov V.V., Khodov I.A., Nikitina L.E.  Conjugate of meso-carboxysubstituted-BODIPY with thioterpenoid as an effective fluorescent probe: Synthesis, structure, spectral characteristics, and molecular docking  // Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. ‒ 2022. ‒ V. 268. – Art. 120638.
  26. Guseva G.B., Nuraneeva E.N., Berezin M.B., Antina E.V.   Effect of meso-substituents and solvent on the photo- and thermal stability of BODIPY dyes // Journal of Photochemistry and Photobiology A: Chemistry. ‒ 2022. ‒ V. 423, №  1. – Art. 113620.
  27. Ksenofontov  A.A., Bocharov P.S., Ksenofontova K.V., Antina E.V.  Water-Soluble BODIPY-Based fluorescent probe for BSA and HSA detection // Journal of Molecular Liquids. ‒ 2022. ‒ V. 345. – Art. 117031.
  28. Ksenofontov A.A., Lukanov M.M., Bocharov P.S. Can machine learning methods accurately predict the molar absorption coefficient of different classes of dyes? // Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. ‒ 2022. ‒ V. 279. – Art. 121442.
  29. Ksenofontov  A.A., Lukanov M.M., Bocharov P.S., Berezin M.B., Tetko I.V.   Deep neural network model for highly accurate prediction of BODIPYs absorption // Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. ‒ 2022. ‒ V. 267, Pt 2. – Art. 120577.
  30. Nuraneeva E.N., Antina E.V., Guseva G.B., Berezin M.B., V'yugin A.I.   Effects of halogen substitution on the photostability and thermal degradation of boron(III), zinc(II) and cadmium(II) dipyrrinato complexes // Inorganica Chimica Acta. ‒ 2018. ‒ V. 482. – P. 800–806.
  31. Nuraneeva E.N., Guseva G.B., Antina E.V., V'yugin A.I. Influence of structural and solvation factors on the photodestruction and efficiency of singlet oxygen generation by luminophores based on iodo- and bromosubstituted zinc(II), cadmium(II) and boron(III) dipyrromethenates  // Journal of Photochemistry and Photobiology A: Chemistry. ‒ 2022. ‒ V. 426, № 7. – Art. 113789.
  32. Nuraneeva E.N., Guseva G.B., Antina E.V., Lodochnikova O.A., Islamov D.R., Nikitina L.E.  Influence of structural and solvation factors on spectral properties and lipophilicity of iodo- and bromosubstituted zinc(II), cadmium(II) and boron(III) dipyrromethenates  // Dyes and Pigments. ‒ 2022. ‒ V. 201. – Art. 110202.
Spektrofluorimetr SM 2203
type:Infrared Spectrometers / Spectrophotometers
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