Fluorine Atoms Research Articles

COSMO-RS guided screening of ionic liquids for the separation of fluorinated greenhouse gases R-410A: Delving into anion, cation effects, and hydrogen bond dynamics

Reclamation of high-GWP near-azeotropic refrigerant R-410A (50 wt% R-32 (difluoromethane) + 50 wt% R-125 (pentafluoroethane)) can be an effective way to mitigate the greenhouse effect and achieve a circular economy. Efficient ionic liquids (ILs) as extractants needed to be found for the extractive distillation (ED) separation process of R-410A. Given the numerous combinations of cations and anions in ILs, the discovery of an efficient IL via experimental methods proves to be an exceedingly complex task. In this work, the solubilities of R-32, and R-125 in 840 conventional ILs (comprised of 20 cations and 42 anions) were analyzed based on infinite dilution activity coefficient. The absorption mechanisms of R-32 and R-125 in ILs were elucidated by analyzing excess enthalpy (HE), excess Gibbs free energy (GE)) and surface charge density distribution through COSMO-RS (Conductor-like Screening Model for Real Solvents). Results revealed that HE and GE of the mixture formed by R-125 and most ILs surpassed those of R-32, resulting in higher solubility of R-32 in most ILs compared to R-125. Structural changes of anions and cations had a greater effect on the solubility of R-125 in ILs. It is found for the first time that the existence of a strong hydrogen bond donor region in cations/anions generated intense repulsion with the hydrogen atom in R-125. Furthermore, a large area of weak polarity on the surface of cations/anions was difficult to form an effective charge shield with fluorine atoms in R-125, thus inhibiting the dissolution of R-125. Finally based on the identified interaction sites, combined with melting point and viscosity, some novel functional ILs with high selectivity for R-32 + R-125 were designed and determined for actual separation process. These findings significantly enrich the understanding of the solubility mechanism and provide theoretical guidance for designing new ILs for R-410A reclamation.

Novel thienopyrimidones targeting hepatic and erythrocytic stages of Plasmodium parasites with increased microsomal stability

Based on the structure of a previously identified hit, Gamhepathiopine 1, which showed promising antiplasmodial activity, but poor microsomal stability, several strategies were investigated to improve the metabolic stability of the compounds. This included the introduction of fluorine or deuterium atoms, as well as carbocyclic groups. Among the new compounds, the 2-aminocyclobutyl derivative 5g demonstrated enhanced microsomal stability compared to compound 1, while retaining antiplasmodial activity against erythrocytic and hepatic stages of Plasmodium, without significant cytotoxicity against primary hepatocytes.

Rearrangements of the Radical Cations of 3-Aryl-5-fluoroisoxazoles: Further Evidence for Existence of Benzocyclopropenyl Cation.

The fragmentation reaction of the radical cations of 3-aryl-5-fluoroisoxazoles formed via EI-MS is described. A new rearrangement accompanied by fluorine atom migration is discovered. A mechanistic rationale for the rearrangement supporting the existence of a fluorinated benzocyclopropenyl cation was proposed based on the experimental data and quantum chemical calculations.

Reactions of Halogenated Acetic and Propionic Acids with Fluorine Atoms

Reactions of Halogenated Acetic and Propionic Acids with Fluorine Atoms

Regiocontrol Using Fluoro Substituent on 3,6-Disubstituted Arynes.

The effect of fluoro substituent on the regioselectivity of several reactions of 3,6-disubstituted arynes was studied. These arynes contained another inductively electron-withdrawing substituent other than fluorine. A reasonable degree of regiocontrol was achieved in the (3 + 2) cycloaddition reaction of 3,6-disubstituted aryne containing both fluorine and bromine atoms with benzyl azide. Furthermore, the insertion reaction of aryne into Sn-F σ-bonds and the three-component coupling reaction involving the insertion of aryne into C=O π-bonds also led to the high degree of regiocontrol.

Desorption properties of the R600, R134a and their mixtures in several MOF structures: A molecular dynamics study

The efficiency of organic Rankine cycle is expected to be enhanced via using metal organic heat carriers. Thus, it is important to investigate the properties of organic working fluid in metal organic frameworks (MOFs). In this paper, molecular dynamics method was employed to study the desorption properties of R600, R134a, and their mixtures in MOF-5, IRMOF-16, and MOF-200 structures. The results show that the desorption capacity of pure working fluids are negatively correlated with their molecular size. In mixed refrigerant systems, the desorption of the working medium is competitive, and the higher the proportion of fluorine atoms in the system, the greater the desorption heat in IRMOF-16. It is noteworthy that the behavior of the desorption heat in the other two MOFs is diametrically opposed to this result. The desorption capacity is positively correlated with the average pore size, specific surface area, and porosity of the MOF. The self-diffusion coefficient of the working medium in MOF is inversely proportional to its molecular weight, but directly proportional to its molecular size and to the pore size of MOF.

Unveiling the Potential of Colorless Polyimide‐Derived Laser‐Induced Graphene: A Novel Pathway for Advanced Sensor and Energy Harvester Performance

AbstractThe potential of laser‐induced graphene (LIG), recognized for its distinct attributes in diverse fields, has significantly grown. However, the creation of LIG using colorless polyimide (CPI) films remains unexplored. This research sheds light on the graphitization technique for generating LIG from CPI films via laser techniques, a process validated through ReaxFF simulations. It is also illustrated that CPI integrated with fluorine atoms possesses an elevated porous configuration, rendering it apt for high‐sensitivity, low‐detection limit pressure sensors. The pressure sensor, constructed with LIG derived from CPI, showcases superior performance metrics such as an exceptional sensitivity rate of 60.340 kPa−1 in low‐pressure ranges (1.0–1.5 kPa), prompt response and recovery intervals (27/36 ms), and commendable durability. The sensor's ability is further validated to precisely track human movements. Moreover, the study employs the LIG sourced from CPI as a dielectric‐to‐dielectric triboelectric nanogenerator (TENG), yielding a peak power output of 411.4 mW m−2 under a 40 MΩ load resistance. The CPI‐based LIG offers increased porosity in comparison to traditional LIG, which aids in superior functioning in pressure sensors and TENG devices. This research offers a fresh perspective on the application possibilities of CPI‐sourced LIG, notably in pressure sensors and energy harvesting devices.

An investigation on spectroscopic, wavefunction dependent reactivity, docking and anti-Covid-19 ability of flupentixol dihydrochloride: DFT and MD simulations at different temperatures

A detailed vibrational analysis of flupentixol dihydrochloride (FDC) is performed by Density Functional Theory (DFT) calculations. Wavefunction reactivity properties and Atoms In Molecules (AIM) analysis are also performed. There is enormous O1-H1B…Cl1, N1-H1A…Cl1 and C9-H9A…F3B intermolecular hydrogen bonding in FDC. Electrons were resonated on the aromatic rings without any interference with aliphatic moiety of both highest occupied molecular orbital (HOMO) and in least unoccupied molecular orbital (LUMO) which is due to participation of fluorine atom intermolecular hydrogen bonding with adjacent C–H. The electron localization function (ELF) shows under populated N-C single bonds of ring A owing to the strong electron withdrawing effect of nitrogen atoms. SARS-CoV-2 main protease with FDC had energy −80 kcal/mol. With the help of molecular dynamics (MD), radial distribution functions (RDF) are calculated to identify the most critical interaction with water molecules.

N-Heterocyclic Carbenes with Polyfluorinated Groups at the 4- and 5-Positions from [3 + 2] Cycloadditions between Formamidinates and cis-1,2-Difluoroalkene Derivatives.

We herein report the formation of fluorinated N-heterocyclic carbenes (NHCFs) that bear fluorine atoms at the 4- and 5-positions of the imidazol-2-ylidene ring. Treatment of sodium N,N'-bis(aryl)formamidinates with tetrafluoroethylene followed by the addition of LiBF4 induced a [3 + 2] cycloaddition to afford 4,5-difluorinated imidazolium salts, which served as the precursors for 4,5-difluorinated NHCs. A key feature of this procedure is its applicability to other perfluorinated compounds, which enabled us to incorporate polyfluorinated functional groups at 4- and 5-positions on the imidazol-2-ylidene skeleton. Thus, employing octafluorocyclopentene and hexafluorobenzene led to the formation of 4,4,5,5,6,6-hexafluoro-1,3-diaryl-3,4,5,6-tetrahydrocyclopenta[d]imidazolium (CypIPrF·HBF4) and 4,5,6,7-tetrafluoro-1,3-diarylbenzimidazolium (BIPrF·HBF4) salts, respectively. A thorough NMR analysis of these NHCFs, their selenium adducts, and their tricarbonyl nickel complexes, (NHCF)Ni(CO)3, demonstrated that the fluorine substituents, contrary to expectations, tend to act as electron donors owing to the considerable positive mesomeric effect, while the perfluorocyclopentene-fused and tetrafluorobenzo-fused rings are pure electron acceptors due to their strong negative inductive effect. The unique and increased π-accepting character of the perfluorocyclopentene-fused and tetrafluorobenzo-fused NHCFs in both stoichiometric and catalytic reactions is further demonstrated by employing (NHCF)Ni(CO)3 and (NHCF)AuCl species, respectively. Moreover, an analysis of the % buried volume (%Vbur) values clearly suggests that the modification of the NHC backbone with polyfluorinated groups can drastically alter the electronic properties of the NHC ligand without substantially changing its steric properties. Our experimental results were further corroborated by a series of computational calculations.

Synthesis and Biological Evaluation of Benzothiazolyl-pyridine Hybrids as New Antiviral Agents against H5N1 Bird Flu and SARS-COV-2 Viruses.

A novel series of benzothiazolyl-pyridine hybrids 8a-h and 14a-e were produced from the reaction of enamine derivative 4 with each of the arylcyanoacetamides 5a-h and cyanoacetohydrazides 9a-e. The new products were characterized by spectral techniques (IR, 1H NMR, 13C NMR, and MS). Biological evaluation of 8a-h and 14a-e in vitro against H5N1 and SARS-COV-2 viruses showed that several compounds had significant activity. Compounds 8f-h, which contain fluorine atoms, have better activity against H5N1 and anti-SARS-CoV-2 viruses than the other compounds included in this study. Compound 8h has a trifluoromethyl group at position-3 of the phenyl ring and exhibits a high activity against H5N1 virus with 93 and 60% inhibition at concentrations of 0.5 and 0.25 μmol/μL, respectively, among the tested compounds, and it also showed anti-SARS-CoV-2 virus with a half-maximum inhibition rate of 3.669 μM, among the remaining compounds. The mechanism of action of 8f-h, which is expected to be repurposed against COVID-19, was investigated. The results showed that the compounds have virucidal effects at different stages of the three mechanisms of action. Furthermore, compounds 8f-h were found to possess CoV-3CL protease inhibitory activities with IC50 values of 544.6, 868.2, and 240.6 μg/mL, respectively, compared to IC50 = 129.8 μg/mL of the standard drug lopinavir. Interestingly, compounds 8f-h also showed high inhibitory activity against the H5N1 virus as well as the SARS-CoV-2 virus. Moreover, compounds 8f-h fit admirably into the active site of the SARS-CoV-2 main protease (PDB ID: 6LU7) using the molecular docking Moe software 2015.10.

Complete Peripheral Fluorination of the Small‐Molecule Acceptor in Organic Solar Cells Yields Efficiency over 19 %

AbstractDue to the intrinsically flexible molecular skeletons and loose aggregations, organic semiconductors, like small molecular acceptors (SMAs) in organic solar cells (OSCs), greatly suffer from larger structural/packing disorders and weaker intermolecular interactions comparing to their inorganic counterparts, further leading to hindered exciton diffusion/dissociation and charge carrier migration in resulting OSCs. To overcome this challenge, complete peripheral fluorination was performed on basis of a two‐dimensional (2D) conjugation extended molecular platform of CH‐series SMAs, rendering an acceptor of CH8F with eight fluorine atoms surrounding the molecular backbone. Benefitting from the broad 2D backbone, more importantly, strengthened fluorine‐induced secondary interactions, CH8F and its D18 blends afford much enhanced and more ordered molecular packings accompanying with enlarged dielectric constants, reduced exciton binding energies and more obvious fibrillary networks comparing to CH6F controls. Consequently, D18:CH8F‐based OSCs reached an excellent efficiency of 18.80 %, much better than that of 17.91 % for CH6F‐based ones. More excitingly, by employing D18‐Cl that possesses a highly similar structure to D18 as a third component, the highest efficiency of 19.28 % for CH‐series SMAs‐based OSCs has been achieved so far. Our work demonstrates the dramatical structural multiformity of CH‐series SMAs, meanwhile, their high potential for constructing record‐breaking OSCs through peripheral fine‐tuning.

Complete Peripheral Fluorination of the Small-Molecule Acceptor in Organic Solar Cells Yields Efficiency over 19 .

Due to the intrinsically flexible molecular skeletons and loose aggregations, organic semiconductors, like small molecular acceptors (SMAs) in organic solar cells (OSCs), greatly suffer from larger structural/packing disorders and weaker intermolecular interactions comparing to their inorganic counterparts, further leading to hindered exciton diffusion/dissociation and charge carrier migration in resulting OSCs. To overcome this challenge, complete peripheral fluorination was performed on basis of a two-dimensional (2D) conjugation extended molecular platform of CH-series SMAs, rendering an acceptor of CH8F with eight fluorine atoms surrounding the molecular backbone. Benefitting from the broad 2D backbone, more importantly, strengthened fluorine-induced secondary interactions, CH8F and its D18 blends afford much enhanced and more ordered molecular packings accompanying with enlarged dielectric constants, reduced exciton binding energies and more obvious fibrillary networks comparing to CH6F controls. Consequently, D18:CH8F-based OSCs reached an excellent efficiency of 18.80 %, much better than that of 17.91 % for CH6F-based ones. More excitingly, by employing D18-Cl that possesses a highly similar structure to D18 as a third component, the highest efficiency of 19.28 % for CH-series SMAs-based OSCs has been achieved so far. Our work demonstrates the dramatical structural multiformity of CH-series SMAs, meanwhile, their high potential for constructing record-breaking OSCs through peripheral fine-tuning.

Dinuclear Gold-Catalyzed para-Selective C-H Arylation of Undirected Arenes by Noncovalent Interactions.

The regioselectivity of C-H functionalization is commonly achieved by directing groups, electronic factors, or steric hindrance, which facilitate the identification of reaction sites. However, such strategies are less effective for reactants such as simple monofluoroarenes due to their relatively low reactivity and the modest steric demands of the fluorine atom. Herein, we present an undirected gold-catalyzed para-C-H arylation of a wide array of monofluoroarenes using air-stable aryl silanes and germanes at room temperature. A high para-regioselectivity (up to 98 : 2) can be realized by utilizing a dinuclear dppm(AuOTs)2 (dppm=bis(diphenylphosphino)methane) as the catalyst and hexafluorobenzene as the solvent. This provides a general and practical protocol for the concise construction of structurally diverse para-arylated monofluoroarenes through C-H activation manner. It features excellent functional group tolerance and a broad substrate scope (>80 examples). Besides, this strategy is also robust for other simple monosubstituted arenes and heteroarenes. Our mechanistic studies and theoretical calculations suggest that para-C-H selectivity arises from highly electrophilic and structurally flexible dinuclear Ar-Au(III)-Au(I) species, coupled with noncovalent interaction induced by hexafluorobenzene.

Novel strategy for reducing the minimum miscible pressure in a CO2–oil system using nonionic surfactant: Insights from molecular dynamics simulations

Effective CO2-oil miscibility is a vital factor in optimizing oil production during CO2 flooding and enhancing CO2 storage capacity. This research investigates the impact of various surfactants, temperatures, and pressures on CO2-oil interfacial tension (IFT) through experimental measurements. It also evaluates the reduction in minimum miscible pressure (MMP). Subsequently, molecular dynamics (MD) simulations analyze gas-liquid miscibility, focusing on relative concentration, interaction energy, radial distribution function (RDF), and miscibility degree (Dmix). Results indicate that introducing a compound nonionic surfactant SF significantly reduces IFT and MMP, achieving an impressive 19.59% MMP reduction. Moreover, SF inclusion boosts Dmix by 8.57%, reflecting enhanced miscibility. The highest absolute value of average interaction energy (EInter) is observed, primarily driven by van der Waals interactions. SF's augmented CO2 coordination number contributes to improved Dmix and reduced MMP. SF's nonpolar groups react with CO2, reducing asymmetric forces between phases and lowering IFT. Electronegative fluorine atoms in SF interact with electron-deficient carbon atoms in CO2, heightening CO2 solubility. Elevated system pressure or reduced temperature amplifies EInter, the coordination number, and subsequently enhances Dmix. Experimentally measured MMP results closely align with MD simulations, with an average relative error of 4.63%. This study elucidates CO2-oil miscibility mechanisms on experimental and molecular scales, offering a promising avenue for future CO2 flooding research.

New Molecular Design, Step-Saving Synthesis, and Applications of Indolocarbazole Core-Based Oligo(hetero)arenes.

In this work, we have successfully synthesized 15 new examples (LLA01-06; LinLi01-10) of small-molecule hole-transporting materials (HTM) using the less explored indolocarbazole (ICbz) as core moiety. Different from previously reported ICbz HTMs, LinLi01-10 exhibit new molecular designs in which 3,4-ethylenedioxythiophene (EDOT) units are inserted as crucial π-spacers and fluorine atoms are introdcued into end-group molecules. These substantially improve the materials solubility and device power conversion efficiencies (PCEs) while fabricated in perovskite solar cells (PSC). More importantly, LinLi01-10 are generated by a sustainable synthetic approach involving the use of straightforward C-H/C-Br couplings as key transformations, thus avoiding additional synthetic transformations including halogenation and borylation reactions called substrate prefunctionalizations usually required in Suzuki reactions. Most HTM molecules can be purified simply by reprecipitations instead of conducting column chromatography. In contrast to LLA01-06 without additional EDOT moieties, PSC devices using LinLi01-10 as hole-transport layers display promising PCEs of up to 17.5%. Interestingly, PSC devices employing seven of the LinLi01-10 as hole-transport molecules, respectively, are all able to show an immediate >10% PCE (t = 0) without any device oxidation/aging process that is necessary for the commercial spiro-OMeTAD based PSCs.

Synthesis and Antiphytopathogenic Activity of Novel Oxazolidine-2,4-diones Bearing Phenoxypyridine Moiety.

In the present study, we conducted optimization of pyramoxadone and synthesized a series of novel oxazolidinediones. Antifungal assays showed that these compounds exhibited moderate to excellent antifungal activity against various pathogens. Further SAR analysis revealed that the introduction of substituents to the benzene ring of the phenoxy group or the inclusion of bulky groups, such as tert-butyl, on the aniline moiety, had a detrimental effect on the activity. However, the inclusion of fluorine atoms in the aniline moiety significantly enhanced the antifungal efficacy. Notably, compound 2-4 displayed significantly higher activity compared to both pyramoxadone and famoxadone against R. solani, B. cinerea, S. sclerotiorum, and P. oryzae, where it demonstrated EC50 values of 1.78, 2.47, 2.33, and 2.23 μg/mL, respectively. Furthermore, compound 2-4 exhibited potent protective and curative effects against the tomato gray mold in vivo. A mechanistic investigation revealed that compound 2-4 significantly impacted the mycelial morphology, inhibited spore germination, and impeded mycelial respiration, ultimately leading to the inhibition of pathogenic fungus growth. These findings indicate that compound 2-4 has the potential to serve as a cyt bc1 inhibitor and should be further investigated for development.

On the relativistic effects on 19F nuclear magnetic resonance chemical shifts in the presence of iodine atoms

In this paper, the influence of the relativistic effects on 19F NMR chemical shifts has been thoroughly investigated in diverse fluorine compounds containing one or more iodine atoms. It was found that the magnitude of the relativistic correction to fluorine shielding constant strongly depends on the arrangement of iodine atom(s) in molecule relative to the fluorine atom under consideration. Thus, specific cases were found where the relativistic corrections to fluorine shielding constants reached at as much as 6–8 ppm, causing noticeable changes in the corresponding fluorine chemical shifts. In general, the relativistic corrections to fluorine shielding constants were found to vary in the range of 0–3 % of their nonrelativistic values.

High-Performance Nonfused Electron Acceptor with Precisely Controlled Side Chain Fluorination.

Modification of the molecular packing of nonfullerene acceptors through fluorination represents one of the most promising strategies to achieve highly efficient organic solar cells (OSCs). In this work, three nonfused electron acceptors, namely, DTCBT-Fx (x = 0, 5, 9) with precisely controlled amounts of fluorine atoms in the side chains are designed and synthesized, and the effect of side chain fluorination is systematically studied. The results demonstrate that the light absorption, energy levels, molecular ordering, and film morphology could be effectively tuned by precisely controlling the side chain fluorination. DTCBT-F5 with an appropriate fluorine functionalization exhibits suitable miscibility with the donor polymer (PM6), leading to diminished charge recombination and improved charge carrier mobility. Consequently, a promising power conversion efficiency of 12.7% was obtained for DTCBT-F5-based solar cells, which outperforms those OSCs based on DTCBT-F0 (11.4%) and DTCBT-F9 (11.6%), respectively. This work demonstrates that precise control of the fluorine functionalization in side chains of nonfused electron acceptors is an effective strategy for realizing highly efficient OSCs.

The influence of Al2O3 concentration on the NaYF4 crystallization in oxyfluoride glass–ceramics

AbstractThe influence of Al2O3 addition on the precipitation of NaYF4 crystals in oxyfluoride glasses has been investigated through the thermal, structural, and optical characterization of the parent glasses and corresponding glass–ceramics (GCs). The high‐resolution transmission electron microscopy analysis of the GC with 5 mol% of Al2O3 shows the presence of phase‐separated droplets about 69 nm in size containing several NaYF4 nanocrystals with the diameter of about 10–15 nm. Raman and magic angle spinning nuclear magnetic resonance (MAS‐NMR) spectroscopy were used to examine the structural changes attributed to the addition of Al2O3. The 19F MAS‐NMR analysis indicated that fluorine atoms are present in different chemical environments (Na–F, Na–Si–F, Na–Al–F, and NaYF4). The increasing amount of Al2O3 reduces the crystallization of NaYF4 phase due to the increased fraction of fluorine bound in Na–Al–F environments. The visible luminescence investigation of the glasses and GCs demonstrated that the intensity of Er3+ ions emission transitions in the GCs was higher than that of the parent glass. This difference was attributed to the presence of Er3+ ions bound in NaYF4 crystalline phase. Further evidence that the Er3+ ions were present in NaYF4 phase was provided by the fact that the excited level Er3+:4S3/2 lifetime was increased in GCs as compared to parent glass.

SYNTHESIS AND PROPERTIES OF NEW 1-HYDRAZINOCARBONYLMETHYL-7-BROMO-5-PHENYL-3-ARYLYDENE-1,2-DIHYDRO-3H-1,4-BENZODIAZEPIN-2-ONES

It is known that 1,4-benzodiazepines have neurotropic properties. Previously, we synthesized a series of 3-arylidene-1,2-dihydro-3H-1,4-benzdiazepin-2-ones 11-18 and showed that they exhibit significant analgesic activity. They also show significant affinity for central benzodiazepine receptors and TSPO receptors CNS. With this in mind, we have previously modified the series of 3-arylidene-1,2-dihydro-3H-1,4-benzodiazepin-2-ones by alkylation of 3-arylidene-1,2-dihydro-3H-1,4-benzodiazepin-2-ones with monobromoacetic acid methyl ester to the first position of the 1,4-diazepine ring to obtain 1-methoxycarbonylmethyl-7-bromo-5-phenyl-3-arylidene-1,2-dihydro-3H-1,4-benzodiazepin-2-ones 19-26, which showed pronounced analgesic activity. The aim of this work is to synthesize and study the affinity for CBR and TSPO receptors 1-hydrazinocarbonylmethyl-7-bromo-5-phenyl-3-arylidene-1,2-dihydro-3H-1,4-benzodiazepin-2-ones 27-31, which have not been previously described in the literature. Compounds 27-31 were synthesized as a result of the reaction of 1-methoxycarbonylmethyl-7-bromo-5-phenyl-3-arylidene-1,2-dihydro-3H-1,4-benzodiazepin-2-ones 19-26 with hydrazine hydrate while stirring the components in ethanol. The yields of the reaction products were 65-92%. It was shown that the hydrazinolysis technique used provides high yields of the target compounds. The structure of the synthesized compounds was confirmed by mass spectrometry and 1H NMR spectroscopy. The affinity of the synthesized compounds to the central benzodiazepine receptors CNS (CBR) and TSPO receptors CNS was studied. The affinity of compounds 27-31 was determined in vitro by radioligand analysis by their ability to displace the commercial radioligands [3H] flumazenil and [3H]PK11195 from their specific binding sites in the GABAA receptor complex and TSPO receptors of the synaptic and the mitochondrial fractions of the rat brain membranes, respectively. Compound 27 displaces the commercial [3H]flumazenil radioligand from its specific binding sites in the GABAA receptor complex by 80.1%, and simultaneously exhibits a very low affinity for TSPO receptors. Derivative 27 is the most potent CBR ligand among the investigated compounds and it is a promising compound for pharmacological research. It has been established that in the synthesized series of 3-fluorobenzylidene derivatives, varying the position of the fluorine atom in the benzylidene fragment leads to change affinity for TSPO receptors. It has been established that the para- position of the fluorine atom in the 3-benzylidene radical of the 1,4-benzodiazepin-2-one molecule is the most important descriptor that determines their affinity for the TSPO receptors. These data agree with the data available in the literature on the effect of the position of chlorine and bromine atoms in the 3-benzylidene radical of the 1,4-benzodiazepin-2-one molecule on the affinity for the TSPO receptors. It was found that the main structural fragment that determines the affinity of binding of 3-benzylidene derivatives to TSPO receptors is the presence of electronegative substituents in the para-position of the benzylidene fragment: para–Hal>>оrtho–Hal>meta–Hal (affinity for TSPO) (Hal= Br, F) Thus, the expediency of further study of this class of compounds is shown.