ZINC(II) COMPLEXES WITH 2,1,3-BENZOTHIADIAZOLE AND 2-PHENYLBENZOTHIAZOLE DERIVATIVES: SYNTHESIS, STRUCTURE AND PHOTOPHYSICAL PROPERTIES тема диссертации и автореферата по ВАК РФ 00.00.00, кандидат наук Пылова Екатерина Константиновна

• Пылова Екатерина Константиновна
• кандидат наук
• 2025

Оглавление диссертации кандидат наук Пылова Екатерина Константиновна

Table of content

List of abbreviations

Introduction 7 Literature review

Chapter 1.1.1: General information about 2,1,3-benzothiadiazole and its properties

Chapter 1.1.2: 4-amino-2,1,3-benzothiadiazole derivatives: synthesis and properties

Chapter 1.1.2.1: Organic derivatives of NH2-btd

Chapter 1.1.2.2: Metal-organic complexes with NH2-btd derivatives 31 Chapter 1.2: 2-(2'-aminophenyl)benzothiazole and its derivatives: synthesis and

properties

Chapter 1.2.1: Organic derivatives of NH2-pbt

Chapter 1.2.2: Metal-organic complexes with NH2-pbt derivatives

Chapter 1.3: Conclusion

Results and discussion

Chapter 2: Coordination of Zn(II) halides to native NH2-btd and NH2-pbt 55 Chapter 2.1.1: Syntheses and characterization of Zn(II) halide complexes with NH2-btd 55 Chapter 2.1.2: Syntheses and characterization of Zn(II) halide complexes with NH2-pbt

Chapter 2.2.1: Luminescent properties of Zn(II) halide complexes with NH2-btd

Chapter 2.2.2: Luminescent properties of Zn(II) halide complexes with NH2-pbt

Chapter 2.3: Conclusion

Chapter 3: Coordination of Zn(II) to amidine derivatives of NH2-btd and NH2-pbt

Chapter 3.1.1: Synthesis and characterization of new amidine ligands

Chapter 3.1.2: Synthesis and characterization of amidinate Zn(II) chloro complexes

Chapter 3.1.3: Synthesis and characterization of amidinate Zn(II) ethyl complexes

Chapter 3.2: Luminescent properties of amidinate Zn(II) complexes

Chapter 3.3: Conclusion

Chapter 4: Visible-light photocatalysis with NH2-pbt derivatives

Chapter 4.1: Introduction to EnT

Chapter 4.1.1: Mechanism and applications of TTEnT

Chapter 4.1.2: TTEnT in [2+2] photocycloadditions

Chapter 4.2.1: Results

Chapter 4.2.2: Scope exploration with NH2-pbt as photosensitizer

Chapter 4.2.3: Mechanistic studies

Chapter 4.3: Conclusion

Summary of results and conclusions

Experimental part

References

Введение диссертации (часть автореферата) на тему «ZINC(II) COMPLEXES WITH 2,1,3-BENZOTHIADIAZOLE AND 2-PHENYLBENZOTHIAZOLE DERIVATIVES: SYNTHESIS, STRUCTURE AND PHOTOPHYSICAL PROPERTIES»

Introduction

Luminescence is the emission of light from atoms, ions or molecules in the ultraviolet (UV), visible, or near infrared (NIR) region of the electromagnetic spectrum. This process occurs when these particles undergo an electronic transition from an excited state to the ground state.1-3 Luminescent materials have firmly entered the life of modern society, playing a key role in a wide range of light-based technologies. From OLED screens4-6 and lighting systems7 to safety signal technology,8 chemical sensors,9,10 solar cells,8 information storage,8 photovoltaic applications,11,12 photocatalysis,8,13 optical thermometry,8 bioimaging/biosensing,8,9,14,15 disinfection,1 anti-counterfeiting,8,16 photodynamic therapy,17-20 and agriculture applications,1,21 these materials are everywhere around us. Current research is oriented towards the development of new materials to enhance the efficiency, operational lifetimes, and performance of the devices. In addition, in order to reduce the environmental impact, sustainable processes and the use of abundant and harmless metals are sought after. Among the latter, zinc is increasingly employed in material sciences due to its low-cost, availability and low-toxicity and will be the focus of this PhD work.22-28 Among the goals to achieve are strong white light emission, high contrast of OLED devices, higher quantum yields, and avoiding issues like material degradation, luminescence quenching, and technical problems in large-scale industrial production. Researchers create new compounds by searching the right balance between the properties of known fluorophores and introduction of new functional groups, using different donor and acceptor sequencies and so on. While organic compounds have attracted significant attention in this field,29 the development of light-emitting materials also involves a wide range of other elements from the periodic table (Figure 1). There are many examples of metal-organic compounds and frameworks, for which luminescence is explained via several different mechanisms depending on the electronic structure of the central atom and the ligands.17,30-34 The luminescence of s- and p-metal complexes is typically characterized by a ligand-to-ligand charge transfer mechanism (LLCT), while the luminescence of transitional metal complexes occurs via one of four pathways: metal-centered (MC) transition, metal-to-ligand charge transfer (MLCT), intraligand (IL) transition, or ligand-to-metal-charge-transfer (LMCT).9,35 The understanding of the luminescence mechanisms in each particular case helps to specifically design materials. Overall, the mentioned challenges in light technology encourage the development of new compounds and the investigation of their photophysical properties. This PhD research focuses on designing and characterizing novel photoactive ligands and metal-organic complexes with potential luminescent applications.

Figure 1 - The Periodic Table: selected elements that play a role in luminescent materials (adapted from reference32)

The relevance of the research

In this context, the chemistry of sulfur-nitrogen heterocyclic compounds is currently actively being developed. Notable examples include derivatives of 2,1,3-benzothiadiazoles (btd) and 2-phenylbenzothiazoles (pbt), which will be the focus of this PhD thesis (Figure 2). The simplicity of their synthesis and their many modification possibilities, through the introduction of various substituents into the btd and pbt frameworks, have provided numerous derivatives36-41 with different electronic and photophysical properties.42'43 These compounds have therefore practical implications in many fields of material sciences, for example, they can be used as components of

organic light emitting diodes (OLEDs), organic field-effect transistors (OFED), sensitive sensors,57-59 fluorescent imaging probes,60 dyes,61,62 or solar cells.63-67 Moreover, such compounds have also found applications as fungicides68 or catalysts. 69-71 Besides purely organic derivatives of btd and pbt, their corresponding transition-metal complexes have also attracted interest for several industrial application.72-76

S 2

N

btd

6' 5'

3 2- 3-pbt

Figure 2 - The numbering of atoms in the btd and pbt compounds

H2N 2'-NH2-pbt

From a coordination chemistry perspective, 4-amino-2,1,3-benzothiadiazole (NH2-btd) and 2-(2'-aminophenyl)benzothiazole (NH2-pbt) are particularly interesting derivatives (Figure 2). The presence of the amino group at C4 (btd) or C2' (pbt) in combination with the heterocyclic structure accounts for diverse coordination modes of these compounds, which can be monodentate, chelate or chelate-bridging. Coordination compounds of various compositions have already been described, featuring central metal atoms such as Ni2+, Cu+, Zn2+, Ag+, Cd2+, Re+, and Ir3+, with NH2-btd or NH2-pbt as one of the ligands in their coordination spheres.43,77-81 Moreover, NH2-btd and NH2-pbt can be modified as primary amines to access new organic derivatives, which are interesting as ligands in transition metal complexes and for their photophysical properties. The proximity of the amino group to the conjugated heterocyclic system accounts for the non-covalent interactions in the structure of these compounds (n-n stacking82, inter/intra-molecular hydrogen bonds83), providing intriguing photophysical properties, including aggregation-induced emission (AIE)84,85 or excited state intramolecular proton transfer (ESIPT).83,86,87

Thereby, the design of effective methods for synthesizing novel coordination compounds with fluorophore ligands and the study of their structure, especially, the determination of main structure types, will contribute to improve the understanding of fundamental information about the coordination chemistry of NH2-btd, NH2-pbt and their derivatives. These heterocyclic amines are known to possess photoluminescent properties in the visible-light spectrum range. Synthesizing new derivatives with various substituents (donor/acceptor) would enable to vary/optimize the photoluminescence maxima and their intensities.41,72 Moreover, through complex formation between the ligand and the metal ion, the intensity and position of the emission maximum can vary significantly depending on the nature of the central metal atom. This work focuses on Zn(II) complexes, which are known to exhibit interesting properties, such as mechanochromic features, luminescence, antitumor and antimicrobial activity, antioxidant power and catalytic behavior.88-95 From our point of view, Zn(II) metal-organic compounds are therefore quite perspective as luminescent materials. The emission of Zn complexes is typically characterized by intraligand transitions, since the Zn2+ has a completely filled outer electron shell 3d10. In addition, the luminescence quantum yield of the coordination compounds is usually enhanced compared to the proligands due to an increase in the rigidity of the organic core and a decrease in luminescence quenching by thermal vibrations or photoinduced proton transfer. Studying the photophysical properties of these coordination compounds and identifying composition-structure-property relations, as well as photocatalytic properties is a fundamental task.

State of the art

Over recent years, the chemistry of NH2-btd and their derivatives has been the subject of considerable research and development and continues to be a central point of innovative research.41 Moreover, the coordination chemistry of NH2-btd is highly diverse, due to the ability of this ligand to coordinate in monodentate, chelate, and bridging modes. It was further found, that the photophysical properties of metal-organic complexes of various metals with the same ligand, including d10-ions, exhibit unpredictable changes96,97 (i.e. bands of absorption and emission) that are challenging to explain even through quantum chemical calculations.98 Whereas some Zn(II) complexes have already been reported with this ligand,82,99 a systematic study of the composition-structure-property relation of halide coordination compounds with the same fluorophore has not been conducted for neither NH2-btd or NH2-pbt. The halide substitution is established to affect both the structure of Zn(II) coordination compounds100 and their photophysical properties.101-103

In contrast to NH2-btd, NH2-pbt usually coordinates in a chelating mode via N3-N2' atoms. Several complexes of Co(II),104 Ni(II),79 Re(I),78,80 and Re(V)105 with NH2-pbt have been described. Among them, fluorescence properties have been studied only for [Re(CO)3(NH2-pbt)Cl], which emits in the visible region.80 To date, the coordination chemistry of NH2-pbt is in its early stages and there is a lack of information on the luminescent properties of its metal-organic complexes as well as on the influence of different halide ligands to the photophysical properties of complexes. Therefore, the first part of this work focuses on the study of a series of Zn2+ halide complexes with NH2-btd or NH2-pbt ligands and the impact of halide ion substitution in complexes of similar composition on their luminescent properties.

The design of new ligands based on NH2-btd or NH2-pbt via introduction of additional phosphorus, oxygen, or nitrogen atoms (Figure 3) has been shown to provide more complex coordination to metal centers and influences the chemical behavior of these compounds.72,75,82,99,106,107 The variety of structural scaffolds and coordination modes significantly impacts on the photophysical properties of metal-organic complexes.

A plethora of amidinate ligands are known in the literature, providing access to transition-metal and f-element complexes with numerous applications in catalysis.110-114 A second part of this work will describe the synthesis, luminescence properties and coordination chemistry of amidinate derivatives of ArNCNHR type based on NH2-btd and NH2-pbt (Ar - an aromatic substituent, R - btd or pbt) which have not yet been reported in the literature.

Photocatalytic properties of pbt-derivatives, especially of transition metal complexes, have already been reported (Figure 4),62,70,115-117 including reactions involving triplet-triplet energy transfer (EnT). EnT plays an important role in organic chemistry as it can provide access to various processes, such as cycloadditions, homolytic o-bond cleavage reactions, E/Z isomerization, and deracemization.118 To date, very few data exist on the triplet energies of organic pbt-derivatives and no applications in photocatalysis have been established.117,119 In the last part of this work, through a combined experimental and theoretical approach, new insights in the photophysical properties of various 2-amino-pbt derivatives was obtained and these compounds were then explored as organic photocatalysts in [2+2] cycloaddition reactions.

Main aim of the research

The main aim refers to developing methods for the synthesis of zinc(II) complexes with 4-amino-2,1,3-benzothiadiazole and 2-(2'-aminophenyl)benzothiazole and their amidine derivatives, and to study the structure, luminescent and photocatalytic properties of the resulting compounds.

The objectives of the research

In order to achieve the aim, the following tasks have been formulated: 1) synthesis of various zinc halide coordination compounds with NH2-btd and NH2-pbt ligands;

Figure 4 - Selected examples of photosentisers based on pbt derivatives-

,115-117

2) synthesis of new amidines derived from NH2-btd and NH2-pbt (ArNCNHR: Ar = Ph, Mes; R = btd, pbt);

3) synthesis of Zn complexes incorporating the new amidinate ligands;

4) study of the structure and photoluminescent properties of the obtained Zn-based compounds;

5) exploration of catalytic properties of the obtained compounds in a [2+2]photocycloaddition process.

Novelty of the research

The novelty of the research is to address a fundamental scientific challenge: the synthesis of novel photoactive amidine proligands based on 4-amino-2,1,3-benzothiadiazole and 2-(2'-aminophenyl)benzothiazole, the synthesis of new Zn(II) complexes with NH2-btd and NH2-pbt, amidines based on these amines, as well as in the determination of the structures of the synthesized compounds and the study of their photophysical and photocatalytic properties. A series of zinc complexes was synthesized by reacting NH2-btd or NH2-pbt with zinc halides. The molecular [Zn(NH2-btd)2Hah] or polymeric [Zn(NH2-btd)2Hah] (Hal = Br, I) complexes were obtained depending on the NH2-btd and ZnHah initial ratio (Figure 5). The NH2-btd exhibits different coordination modes in these compounds, which influence their luminescent properties. Reactions of NH2-pbt with zinc halides resulted in the formation of complexes [Zn(NH2-pbt)Hah] (Hal = Cl, Br, I), which were isolated in several phase forms: as [Zn(NH2-pbt)Hah] (Hal = Cl, Br, I; in case of bromo and iodo complexes two polymorphic modifications were obtained) or in the form of co-crystals [Zn(NH2-pbt)Hah]2NH2-pbt (Hal = Cl, Br) (Figure 5). NH2-pbt exhibits chelate coordination via N atoms of heterocycle and amino-group in all cases.

[Zn(NH2-btd)2Br2] [Zn(NH2-pbt)Hal2]

Hal = Cl, Br, I

Figure 5 - Some examples of synthesized Zn-complexes described in this work

Amidines (ArNCNHR) based on NH2-btd and NH2-pbt were synthesized for the first time (Figure 6): PhNCNHbtd, MesNCNHbtd, PhNCNHpbt and MesNCNHpbt. The complexes with amidinate ligands (ArNCNR)- were prepared by two methods. The treatment of ZnEt2 or ZnCh in the presence of KH with corresponding amidines afforded [Zn(ArNCNbtd)Et]2 and [Zn(ArNCNpbt)Et] or

[Zn(ArNCNR)Cl]2, respectively. The structures of new compounds were established by single-crystal X-ray diffraction (Figure 6), and their photophysical properties were studied.

At = Ph, Mes [Zn^CN^Cl^ [Zn(MesNC№bt)Et]

Figure 6 - Synthesized amidines and new Zn complexes described in this work

In light of the few data about applications of pbt derivatives in photocatalysis, especially via EnT mechanisms,117 we have studied the photocatalytic properties of synthesized complexes and organic derivatives in [2+2] photocycloaddition reactions. New tunable organic photosensitizers based on 2-(2'-aminophenyl)-benzothiazole (NH2-pbt) were developed which catalyze [2+2] photocycloaddition reactions of unsaturated acyl imidazoles with styrene. To the best of our knowledge, this is the first application of NHR-pbt derivatives in photocatalysis. The catalytic activity of pbt derivatives was studied with respect to the functional group at C2' and the influence of ESIPT processes. NH2-pbt was employed as a commercially available photosensitizer to synthesize 19 cyclobutane products (Scheme 1) in moderate to good yields with good functional group tolerance.

R1 O

N

I

■N

0=Ar O = H, Alk, Ar

+

(10 equiv.) O = H, Alk, Ar

NHrpbt (20 mol%)

DCM, RT, 21 h blue LED

R1 O

Rj = Me, nBu, Ph

Scheme 1 - [2+2]photocycloaddition catalyzed by NH2-pbt

Theoretical and practical significance

This work provides new insights into the coordination chemistry of Zn(II) with btd- and

pbt-derived ligands. It presents fundamental information on the methods for synthesizing zinc

complexes with NH2-btd, NH2-pbt, and derived amidine ligands, as well as details on the

coordination modes and photophysical properties of these complexes. The dependence of the

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structure of metal-organic compounds derived from NH2-btd and NH2-pbt in the row of zinc chloride, bromide, and iodide series was shown. Moreover, the structure of chloro and ethyl zinc complexes with amidinate ligands were studied. The structural data obtained from this research have been deposited in the Cambridge Crystallographic Database (CCD). Additionally, the stability of mesityl chloro complexes in the presence of atmospheric water was demonstrated. The study highlights the dependence of photoluminescent properties on the mode of ligand coordination, offering a deeper understanding of the luminescent behavior of Zn(II) complexes. For the first time, the tunable nature of pbt derivatives as a catalyst in the [2+2] photocycloaddition reaction of cinnamoyl methylimidazole with styrene was demonstrated. Optimal conditions for the NH2-pbt-catalyzed reaction were identified, and range of cyclobutane products were synthesized.

Defense proposals

- Methods for the synthesis of zinc complex compounds with NH2-btd and NH2-pbt;

- Methods for the synthesis of amidines based on NH2-btd and NH2-pbt and coordination compounds of Zn(II) with them;

- Results concerning the structural features and luminescence properties of the synthesized compounds;

- Optimal conditions for the [2+2] photocycloaddition reaction catalyzed by NH2-pbt through mechanistic studies as well as scope exploration.

Dissertation research methodology and methods

This work is fundamental research in the field of synthetic coordination chemistry and photocatalysis, involving experimental and theoretical studies. In addition to the synthesis of coordination compounds of known ligands, new amidines with fluorophore groups have been obtained, characterized and applied in Zn coordination chemistry. The obtained compounds were isolated as solid phases and characterized by a series of physicochemical methods: X-ray diffraction and X-ray phase analysis (SCXRD and PXRD), elemental analysis (C, H, N, S), IR and NMR spectroscopy. The photophysical properties in solid phases have been studied using diffuse reflectance spectroscopy and luminescence methods, including the determination of excited state lifetimes and quantum yields. In the photocatalysis part of this work, all new organic compounds were characterized via high resolution mass spectrometry (HRMS) and NMR spectroscopy. In addition to optimization studies of [2+2] photocycloaddition reaction catalyzed though pbt derivatives and the scope determination, DFT calculations were employed for describing the interaction of substrate-photocatalyst, S^S0 transitions and T1 level of photocatalysts.

Degree of validity of research findings

The reliability of the research is confirmed based on a combination of physical and physicochemical analysis data. Furthermore, the consistency of the results obtained by various independent methods ensures the reliability of the results. The majority of the results of the work were published in refereed scientific journals, which indicates that the results were recognized as reliable by third-party researchers.

Approbation of the thesis work

The studies of this thesis were presented at 3 international conferences: 58th International Scientific Student Conference (Novosibirsk, 2020); International summer school-conference for young scientists "CS2fE-2022" (France, 2022); 3rd International Symposium "Noncovalent Interactions in Synthesis, Catalysis, and Crystal Engineering" (Novosibirsk, 2024).

Publications

On the topic of the dissertation, 3 articles were published in international journals included in the list of those recommended by the Higher Attestation Commission of the Russian Federation for the publication of dissertation research results and indexed in the international scientific citation system Web of Science.

1) Pylova, E.K.; Khisamov, R.M.; Bashirov, D.A.; Sukhikh, T.S.; Konchenko, S.N. The effect of halides and coordination mode of 4-amino-2,1,3-benzothiadiazole on the luminescence properties of its Zn complexes. CrystEngComm, 2022, 24, 8256-8265, https://doi.org/10.1039/D2CE01215D;

2) Sukhikh, T.S.; Kolybalov, D.S.; Pylova, E.K.; Konchenko, S.N. Luminescent Zn Halide Complexes with 2-(2-Aminophenyl)benzothiazole Derivatives. Inorganics, 2022, 10, 138, https://doi.org/10.3390/inorganics10090138;

3) Pylova, E.K.; Lasorne, B.; McClenaghan, N.; Jonusauskas, G.; Taillefer, M.; Konchenko, S.N.; Prieto, A.; Jaroschik, F.; Chemistry - A European Journal, 2024, 30, 68, 1-7, https://doi .org/10.1002/chem.e202401851.

Personal contribution of the author

The author conducted all the syntheses of amidine proligands, coordination compounds and starting materials for studying photocatalytic properties as well as the preparation of samples for all types of studies used in the thesis. In addition, all IR spectra, quantum-chemical calculations in the Gaussian 16 program package and a part of the photophysical experiments (on Agilent Cary 60 and Agilent Cary Eclipse spectrometers) were carried out personally. The planning of the work

15

and setting of research objectives were carried out in collaboration with the supervisors. The analysis and preparation for publication of the research results were conducted in collaboration with the supervisors and co-authors of the articles.

Relevance to specialty 1.4.1 Inorganic chemistry (Novosibirsk University)

This thesis corresponds to the following fields of research 1.4.1. Inorganic chemistry (chemical sciences): Section 1 "Basic principles of obtaining objects of inorganic chemistry research and materials based on them", Section 2 "Design and synthesis of new inorganic compounds and highly pure substances with specified properties", Section 5 "The relationship between composition, structure and properties of inorganic compounds. Inorganic nanostructured materials", Section 7 "Processes of complexation and reactivity of coordination compounds, reactions of coordinated ligands".

Thesis volume and structure

The thesis is presented on 170 pages and contains 79 figures, 25 tables, 37 schemes. There are introduction, literature review, results and discussions, summary of results and conclusions, experimental part and references.

Literature review

The chemistry of heterocyclic compounds is one of the main areas of the chemical industry and is involved in nearly all fields of modern life. The developed compounds have significant contributions in molecular and cellular biology, medicine, aerospace technologies, optoelectronic technologies, solar cells, dyes, and the chemistry of other functional materials.120 Both 2,1,3-benzothiadiazole (btd) and 2-(phenyl)benzothiazole (pbt) are important chromophores, contributing to their utilization in these applications. The chemistry of organic derivatives of btd and pbt is a well-studied area, that continues to be actively researched, and it is closely related to studying their photophysical properties. A SciFinder search shows that there are approximately 13000 known btd compounds with an amino groupa and over 5000 methodologies of their syntheses. Most btd-based organic compounds have been synthesized for use in optoelectronic devices due to the intrinsic electron-acceptor properties46,121123 of the btd fragment. Comparable data for pbt are more modest: approximately 4500 amino derivativesa and about 1500 synthesis methods are described in the literature. These synthetic ways include the use of microwave or photochemical radiation, reactions under low/high pressure, high temperature, or dark conditions, in solid state, or through electrochemical processing, among many others. It is not feasible to describe such a huge volume of information in one review, so this chapter will focus only on the chemistry of derivatives containing amino groups at the C4 (btd) and C2' (pbt) positions. The numbering of atoms in btd and pbt, as used in the literature and in this review, is shown in the introduction (Figure 2). For simplicity, we use the abbreviations NH2-btd and NH2-pbt for 4-amino-2,1,3-benzothiadiazole and 2-(2'-aminophenyl)benzothiazole, respectively.

This review presents information on the synthetic methods of these heterocycles and their coordination compounds. Additionally, it describes some of their physical properties and information on practical applications.

Заключение диссертации по теме «Другие cпециальности», Пылова Екатерина Константиновна

Summary

This PhD manuscript describes the synthesis and structural characterization of zinc(II) coordination complexes bearing 2,1,3-benzothiadiazole (btd) and 2-phenylbenzothiazole (pbt) derivatives in order to gain a better understanding on the factors that govern their photophysical properties. The first chapter provides a literature overview on the synthesis of 4-amino-btd (NH2-btd) and 2-(2'-aminophenyl)-pbt (NH2-pbt) derivatives, their coordination chemistry and their applications related to their luminescence properties, for example as sensors for various ions. In chapter two, the coordination of various Zn(II) halides (Cl, Br, I, OTf) to NH2-btd or NH2-pbt ligands is described showing a significant difference in coordination behaviour in solid state. All new structures were determined by single-crystal X-ray diffraction, the molecular [Zn(NH2-btd)2Hal2] or polymeric [Zn(NH2-btd)2Hal2] (Hal = Br, I) complexes were obtained depending on the NH2-btd and ZnHal2 initial ratio. The NH2-btd exhibits different coordination modes in these compounds, which influences their luminescent properties. Reactions of NH2-pbt with zinc halides resulted to formation of [Zn(NH2-pbt)Hal2] (Hal = Cl, Br, I), which were isolated in the several phase forms: as [Zn(NH2-pbt)Hal2] (Hal = Cl, Br, I; in case of bromo and iodo complexes two polymorphic modifications were obtained) or in the form of co-crystals [Zn(NH2-pbt)Hal2]2NH2-pbt (Hal = Cl, Br). In case of Zn(OTf)2, two NH2-pbt were introduced into the zinc coordination sphere [Zn(NH2-pbt)2(OTf)2]. NH2-pbt exhibits chelate coordination via N atoms of heterocycle and amino-group in all cases. In the following chapter three, new Zn(II) amidinate complexes are reported derived from mixed amidine ligands bearing two different aromatic moieties, one phenyl or mesityl group and one btd or pbt unit. Two synthetic pathways towards these new Zn(II) complexes have been developed. Salt metathesis employing Zn chlorides and potassium amidinate provided dinuclear complexes, whereas protolysis of the amidine using diethylzinc afforded a dinuclear amidinate zinc ethyl complex, if ligand contains btd moiety, or a monomeric amidinate zinc ethyl complex, if ligand contains pbt fragment. The luminescence properties of all complexes have been investigated, showing a significant influence upon ligand coordination. The final chapter four details an explorative study on the use of the new compounds in photocalysis. It was found that NH2-pbt acts as an efficient organic photosensitizer in the visible-light [2+2] photocycloaddition reaction of various styrenes and dienes with cinnamoyl-derivatives. Some mechanistic understanding has been obtained by a combined experimental and theoretical approach.

Список литературы диссертационного исследования кандидат наук Пылова Екатерина Константиновна, 2025 год

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