Single-crystal X-ray Diffraction Research Articles

Leveraging Ligand Desymmetrization to Enrich Structural Diversity of Zirconium Metal-Organic Frameworks for Toxic Chemical Adsorption.

The discovery of metal-organic frameworks (MOFs) with novel structures provides significant opportunities for developing porous solids with new properties and enriching the structural diversity of functional materials for various applications. The rational design of building units with specific geometric conformations is essential to direct the construction of MOFs with unique properties. Herein, we leverage a ligand desymmetrization approach to construct a series of new MOFs. A flexible tetratopic carboxylate ligand with a tetrahedral geometry was designed and assembled with a Zr6 cluster, generating four Zr-based MOF structures: NU-2600, NU-2700, NU-2800, and NU-1802, in which the ligand configurations and Zr6 cluster connectivities can be controlled by varying solvents and modulators during synthesis. Except for NU-1802, these represent entirely new topologies. Notably, NU-1802 exhibits structural flexibility, with up to a 74% reduction in the unit cell volume as confirmed by single-crystal X-ray diffraction studies. Given their microporous structures, we studied the adsorption behaviors of n-hexane and 2-chloroethyl ethyl sulfide to explore the structure-property relationships of these MOFs. Overall, this work highlights ligand desymmetrization as a powerful method to enrich MOF structural diversity and access complex MOFs with non-default topologies suitable for applications such as toxic gas capture.

Modulating the Supramolecular Assembly of α-Cyclodextrin and Anderson-type Polyoxometalate through Covalent Modifications.

A series of unprecedented supramolecular complexes of covalently modified Anderson-type polyoxometalates (POMs) and α-cyclodextrins (α-CDs) have been obtained and characterized in solid state by single-crystal X-ray diffraction, and in aqueous solution using various techniques including 1H DOSY, 2D NOESY 1H NMR, isothermal titration calorimetry (ITC), and electrospray ionization time-of-flight mass spectroscopy (ESI-TOF-MS). It has been demonstrated that the supramolecular assembly process can be modulated by different covalent modification modes of the Anderson POMs, giving rise to a new type of POM/α-CD complexes featuring organic-inorganic pseudo-rotaxane structures, which are in good contrast to those of POM/γ-CD with poly-rotaxane type structures. Moreover, it is delighted to find that these pseudo-rotaxanes of POM/α-CD exhibit stable chirality in aqueous solution, which has not been accomplished in previously reported POM/γ-CD assemblies.

Frustrated Radical Pairs: From Fleeting Intermediates to Isolable Species.

We present the design and comprehensive investigation of stable para-substituted triarylamine-2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) radical ion pairs (RIPs) generated via single-electron transfer (SET). We quantified the degree of SET in both solution and solid phases, utilising a suite of spectroscopic techniques including IR, EPR, NMR, and single-crystal X-ray diffraction (SC-XRD). Our findings reveal that the extent of SET is significantly influenced by the nature of the substituents (MeO > tBu > Br) and the polarity of the solvent (MeCN > DCM > toluene). The radical ion pair [(pMeOPh)3N]•+[DDQ]•- was unambiguously identified using EPR and UV-vis spectroscopy, and its structure was confirmed by SC-XRD. Detailed analysis indicates an open-shell singlet ground state with a thermally accessible triplet state, as corroborated by EPR, magnetic susceptibility measurements, and DFT calculations. This study offers crucial insights into the mechanistic pathways of RIP formation and tuning both in solution and solid states, laying the groundwork for future exploration of their reactivity and potential applications.

HOST-GUEST INTERACTIONS FACILITATED BY CHALCOGEN BONDING WITHIN SELENADIAZOLE FUNCTIONALISED PORPHYRIN NANOTUBES.

The structural rigidity of tetrakis(4-pyridyl)porphyrin (TPyP) has been utilised to prepare a robust novel porous coordination polymer of composition Cd2(TPyP)(sez)2 (TPyP = 5,10,15,20-tetra(4-pyridyl)porphyrin, sez = 1,2,5-benzoselenadiazole-5-carboxylate). The coordination polymer may be described as a hexagonal porphyrin nanotube (PNT) and has the potential to bind guest molecules through chalcogen bonding. Single crystal X-ray diffraction (SCXRD) data indicate an internal pore diameter ~9 Å which represents ~35% of the crystal volume. Immersion of the PNTs in solvents such as DMSO and CS2 result in the incorporation of these molecules within the nanotubes with chalcogen bonding between host and guest. The crystallographic guest-inclusion investigations are complemented by solid-state 77Se, 13C, 113Cd and 2H NMR studies which provide insights into dynamic behaviour. The porosity of the crystals was further explored using gas adsorption experiments, indicating the reversible uptake of CO2, CH4, H2 and N2. Structure-function relationships are clearly established from complementary crystallographic, NMR and adsorption investigations.

Structural and Photophysical Differences in Crystalline Trigonal Planar Copper Iodide Complexes with 1,2-Bis(methylpyridin-2-yl)disilane Ligands.

We synthesized trigonal planar Cu(I) iodide complexes with 1,2-bis(methylpyridin-2-yl)disilane ligands L1-L4 and investigated how the substitution position of the methyl group on the pyridine ring in σ-π conjugation affects their structure and physical properties. The structures were characterized by NMR, elemental analysis, and single-crystal X-ray diffraction. In the crystalline state, the methylpyridyl groups of CuIL1-CuIL3 were coordinated with Cu(I) in an anticlinal conformation relative to the Si-Si σ bond, whereas those of CuIL4 were coordinated with Cu(I) in a synperiplanar conformation relative to the Si-Si σ bond. The conformational difference in the crystalline state was influenced by the N-Cu-N bite angle and the emission wavelength. CuIL1-CuIL3 exhibited blue-green emission (λem: 476-494 nm), and CuIL4 exhibited green-yellow emission (λem: 512 nm) with high emission quantum yields (Φ: 0.59-0.86) in the crystalline state at 293 K. These Cu(I) complexes exhibited thermally activated delayed fluorescence from the S1 state at 293 K and phosphorescence from the T1 state at 77 K in the crystalline state. The optical properties in the crystalline state were discussed by DFT and TD-DFT calculations. These complexes also displayed aggregation-induced emission in THF-water solution (fw > 80%), although they did not show emission in dehydrated THF.

Combination of Ambient and High-Temperature Beryllium Nitride Motifs in W2Be4N5 and W4Be8N9.

Compounds of transition metals and beryllium have a wide range of applications, from everyday tools to high tech applications. Remarkably, no single ternary beryllium nitride with a transition metal is known. Here, we report on the synthesis and properties of the first transition metal nitridoberyllates, namely W2Be4N5 and W4Be8N9. Both compounds were synthesized in a high-temperature high-pressure approach from Be3N2 and W, using azide generated N2 as an oxidizing agent. The crystal structures, consisting of alternating layers of WN6 trigonal prisms and BeN4 tetrahedra, were elucidated by single-crystal X-ray diffraction (sc-XRD). The separating nitridoberyllate layers show either ambient temperature (α-Be3N2 type) or high temperature (β-Be3N2 type) motifs. W2Be4N5 was further corroborated by infrared (IR), nuclear magnetic resonance (NMR) and UV-VIS spectroscopy and vibrating sample magnetometry (VSM) measurements. The latter revealed a mixed valence with an intermediate oxidation state of 3.5 for the W atoms. Both, the synthesis of the first transition metal nitridoberyllates and the synthesis approach using elemental W pave the way to a new field of nitride chemistry.

Fluorinated Squareimines for Molecular Sieving of Aromatic over Aliphatic Compounds.

The development of more energy-efficient separation technologies is essential. Especially the separation of cyclic aliphatic hydrocarbons from their aromatic counterparts remains a significant challenge due to azeotrope formation and similar physical properties, often requiring energy-intensive processes. Herein, we introduce a novel class of electron-deficient macrocycles with a unique rectangular structure to optimise π···π interactions within the pore, enabling the highly selective molecular sieving of aromatic compounds from mixtures. Utilising dynamic covalent imine chemistry, the squareimine NDI2F42-based crystalline functional material is directly obtained from the reaction mixture in a single self-assembly step in high yields of 84%, alongside the larger NDI2F82 congener, which can be obtained in 69% yield. In vapour sorption and diffusion experiments, NDI2F42 demonstrates rapid adsorption kinetics with selectivities of 97:3 for benzene over cyclohexane and 93:7 for toluene over methylcyclohexane, while single-crystal and powder X-ray diffraction studies confirm that the selectivity is primarily governed by directed π···π interactions.

Crystal structure of AlPCl8

The crystal structure of aluminium phosphorus chloride (systematic name: phosphorus tetrachloride tetrachloridoaluminate), (PCl4)[AlCl4] or AlPCl8, was determined and refined using single-crystal X-ray diffraction data. The compound crystallizes in the orthorhombic space group Pbcm. The asymmetric unit comprises one Al atom, one P atom, and five Cl atoms. The structure is characterized by isolated AlCl4 and PCl4 tetrahedra, isostructural with FePCl8 and GaPCl8.

Studies on the synthesis, crystal structures, biological activities and molecular docking of novel natural methylxanthine derivatives containing piperazine moiety.

A series of novel methylxanthine Mannich base derivatives containing substituted piperazine groups were synthesized through Mannich reaction. The structures of these new compounds were confirmed by NMR, HRMS or elemental analyses, and X-ray single crystal diffraction. Bioassay results showed that some of the compounds exhibit favorable fungicidal and insecticidal potentials. Particularly, compounds IIk, IIq, IIs and compounds If, IIk against Physalospora piricola and Rhizoctonia cerealis, respectively, were comparable with Azoxystrobin and Chlorothalonil; compound Ik exhibited higher potency than Triflumuron against Plutella xylostella L., suggesting its potential as a lead compound for further development in insecticidal applications. Despite possessing weak herbicidal activities, the target compounds, especially the methylxanthine S-Mannich base derivatives I displayed remarkable inhibitory activities toward ketol-acid reductoisomerase (KARI); compounds Ib, If, and Ik which had Ki values of 2.41-8.08 µmol/L can be novel potent KARI inhibitors for deeper exploration. The SARs were analyzed in detail. The molecular docking studies on the highly active inhibitors with KARI provided possible binding modes between inhibitor and the target enzyme. The physicochemical parameter predictions indicated that compounds Ik, IIk, IIq and IIs have "druglike structure" features. The research results in this article may bring a new inspiration to the extensive explorations on new methylxanthine derivatives in pesticide area.

Syntheses, structures and characterization of noncentrosymmetric MZnPO4 (M = K, NH4).

Two phosphates, KZnPO4 and NH4ZnPO4, were successfully synthesized using a solid-state reaction method and characterized via single-crystal X-ray diffraction. Both of their structures feature a three-way skeleton composed of isolated PO4 and ZnO4 tetrahedra, with K+/NH4+ cations occupying the spaces within the frameworks to balance charges. These compounds are isostructural and crystallize in the noncentrosymmetric P63 space group. Their structures were compared, revealing that non-centrosymmetric (NCS) KZnPO4 and NH4ZnPO4 exhibit second harmonic generation (SHG) responses of 0.4 × KDP and 1 × KDP, respectively. Furthermore, by combining the electronic structure and SHG density calculations, we examined the effects of ZnO4 tetrahedra on the SHG response of KZnPO4 and NH4ZnPO4.

Structural nature of pyroelectric effect revisited: Experimental and theoretical studies of synthetic Ni,Al - rich tourmaline

Tourmaline, the first pyroelectric material discovered, is also a promising borosilicate material with non-linear optical and luminescence properties, high thermal stability, high hardness and variable chemical composition. The structural nature of pyroelectricity in tourmaline is a subject of scientific debate since it requires precise structural studies and measurements at elevated temperatures. Here, an in situ high temperature single-crystal and powder X-ray diffraction studies (up to ∼1000 °C) and the direct pyroelectric measurements (up to ∼200 °C) of synthetic Ni, Al-rich tourmaline were performed. The pyroelectric coefficient was calculated from the structural data. The results demonstrate that polyhedra XO9, YO6 and ZO6 exert the greatest influence on the pyroelectric effect. The pyroelectric coefficient of tourmaline is practically independent of boron-oxygen triangles and silicon-oxygen tetrahedra. The primary pyroelectric coefficient of tourmalines could be calculated from single crystal structural data. This study contributes to the synthesis of tourmalines with the required pyroelectric properties and may be used for the study of the nature and properties of other pyroelectric materials.

Characterization of a New Insecticidal Benzothiazole Derivative from Aspergillus sp. 1022LEF against the Fall Armyworm, Spodoptera frugiperda (Lepidoptera: Noctuidae).

The fall armyworm Spodoptera frugiperda is considered one of the most destructive crop pests, posing a significant threat to food and crop security. In this study, we conducted a chemical investigation of the endophytic fungus Aspergillus sp. 1022LEF, leading to the identification of a previously unreported benzothiazole derivative, 6-(2-hydroxyethyl)benzo[d]thiazol-4-ol (HBT). Its structure was unambiguously characterized using extensive spectroscopic methods, including 1D and 2D NMR data, HRESIMS data, and single-crystal X-ray diffraction analysis. The insecticidal assay revealed that HBT possessed remarkable activity against S. frugiperda with an LC50 value of 0.24 mg/mL. Further transcriptomic and proteomic analyses revealed that HBT induced mortality in S. frugiperda by impeding DNA replication and protein synthesis, influencing mitochondria-mediated autophagy, and perturbing hormone synthesis, thereby disrupting the fundamental biosynthetic processes. HBT demonstrated high activity in controlling S. frugiperda, which highlighted its potential use as a lead in the development of biopesticides.

Synthesis, Crystal Structure, Spectroscopic Characterization, In Vitro and In Silico Molecular Docking Studies of Benzyl Tetrazole-N-Isobutyl Acetamide Hybrid

Background: Tetrazole-based compounds are of significant interest due to their potential pharmacological applications. The current study focuses on the synthesis and analysis of such a compound. Objective: This research aims to synthesize the title compound N-(3-methyl-1-phenyl-2-(1Htetrazol- 1-yl) butyl) acetamide, analyze its crystal structure, perform computational studies, and evaluate its potential pharmacological activities and it’s in silico and in vitro supports, specifically antidiabetic and anti-inflammatory properties. Methods: The title compound, C14H19N5O, was synthesized, and its crystal structure was confirmed using single-crystal X-ray diffraction analysis by default parameters. Density Functional Theory (DFT) calculations were performed using the Gaussian 09W software package with the B3LYP/6-311++G (d,p) method to optimize the compound's structure and calculate its HOMOLUMO energy gap, Molecular Electrostatic Potential (MEP), and Mulliken charge distribution. In vitro, antidiabetic and anti-inflammatory activities were assessed and compared with standard drugs by using reported protocols. Additionally, molecular docking studies were conducted with enzymes related to diabetes and inflammation with default parameters, and Auto-Dock 4.2 software was used. Results: The X-ray diffraction analysis confirmed the crystal structure, and the Density Functional Theory (DFT) calculations provided insights into the molecular properties of the compound. Molecular docking experiments with relevant enzymes further supported the significant antidiabetic and anti-inflammatory activities demonstrated in the in vitro tests. Conclusion: The synthesized tetrazole-based compound exhibits promising antidiabetic and antiinflammatory activities, supported by both experimental and theoretical studies, suggesting its potential for further pharmacological investigation.

Cs3LiGe4, One Compound with Two Complementary Structural Descriptions: Isolated [Ge4]4- Tetrahedral Clusters Coordinated by Li+ and Cs+ Cations or One-Dimensional [LiGe4]3- Polyanions Packed within a Matrix of Cs+ Cations?

Reported are the synthesis and structural characterization of Cs3LiGe4, the first structurally characterized lithium-containing cesium germanide. Single-crystal X-ray diffraction data indicate that Cs3LiGe4 crystallizes in an orthorhombic crystal system with the space group Cmcm (no. 63, Person symbol oS32) with unit cell parameters a = 6.950(2) Å, b = 15.503(3) Å, and c = 9.919(2) Å and V = 1068.65(4) Å3. The structure consists of [Ge]44- tetrahedral clusters with the Li atoms positioned in such a way that polyanionic [LiGe]43- chains could be considered as well. Electronic structure calculations indicate an intrinsic semiconductor with a band gap of 0.76 eV. To understand the nuances of the chemical bonding, position-space techniques based on the quantum theory of atoms in molecules, the electron localizability indicator, and their basin intersections were employed confirming the covalent character of the Ge-Ge bonding. The strong polarity of the interactions between [Ge]44- and the surrounding lithium and cesium cations suggests to interpret these as mainly ionic, further supporting the most basic structure rationalization [Cs+]3[Li+][Ge]44-, following the Zintl-Klemm concept. The electron localizability indicator topology affirms the striking similarities between [Ge]44- and molecular As4 tetrahedra in yellow arsenic, further supporting Klemm's pseudoatom concept on a quantum chemical basis.

R2Pt7MnP4-x (R = Ca, Eu): Intrinsic heterostructures based on a combination of AuCu3- and CaBe2Ge2-type fragments with chemically switchable magnetic interplay

Two quaternary phosphide platinides, Eu2Pt7MnP2.96 (I4/mmm, a = 4.0453(7) Å, c = 26.745(4) Å, V = 437.67(17) Å3, Z = 2, R1 = 0.0262, wR2 = 0.0527) and Ca2Pt7MnP3.02 (I4/mmm, a = 4.0027(5) Å, c = 26.735(5) Å, V = 428.34(14) Å3, Z = 2, R1 = 0.0280, wR2 = 0.0673) were synthesized as single crystals and bulk samples, their crystal structures were established from single-crystal X-ray diffraction data and confirmed by powder diffraction and elemental analysis. The compounds crystallize in the tetragonal system, and represent heterostructures built from the alternating layers of AuCu3- and CaBe2Ge2-type fragments. Both compounds are metallic based on the DFT calculations. Chemical bonding analysis reveals a pattern of covalent and ionic interactions within each compound. Magnetic measurements show both compounds to be ferromagnetic, and reveal an interplay between europium and manganese magnetic lattices, indicative of an exchange bias effect.

Rational Design of Crystalline and Enantiomerically Pure Helicenes with Open-Shell Singlet Ground States.

Helicene diradical derivatives have attracted widespread attentions because of their unique magnetic and chiroptoelectronic properties, however, crystalline and enantiomerically pure forms of helicene diradicals are extremely rare. Herein, we describe the rational design and synthesis of o-quinone functionalized helicene diradicals with crystalline enantiomerical purity. Diradical dianion salt Rac-3K and its enantiomers P/M-3K were obtained by reduction of corresponding precursors Rac-3 and P/M-3 with two equivalent potassium graphite in THF in the presence of (di)benzo-18-crown-6. Neutral dioxoborocyclic helicene diradicals (Rac-3B and P/M-3B) were produced by reactions of Rac-3 or P/M-3 with chlorobis(perfluorophenyl)borane (B(C6F5)2Cl. Crystal structures of compounds Rac-3K, Rac-3B and P/M-3K were obtained by single crystal X-ray diffraction. Their open-shell singlet state ground states were confirmed by electron paramagnetic resonance (EPR) spectroscopy, superconducting quantum interference device (SQUID) measurements and theoretical calculations. Their chiroptical properties were investigated by the electronic circular dichroism (ECD) spectroscopy. This work provides the first examples of enantiopure helicene diradical dianions and boron-containing helicene diradicals.

Osmaborane Clusters with B4 and B5 Rings Stabilized in the Coordination Sphere of {OsLn} (Ln = η5-C5Me5 or H2(PPh3)2).

New synthetic routes have been developed to synthesize osmaborane clusters featuring B4 and B5 rings in the coordination spheres of osmium. Thermolysis of [Os(PPh3)3Cl2], 1 in the presence of excess of [BH3·THF] led to the formation of [Os(PPh3)2H2(η4-B4H8)], 2 along with [HOs(PPh3)2B5H10], 3. Cluster 2 features a planar tetraborane ring coordinated to an osmium center in an η4 fashion. Cluster 3 can be considered an osmium analogue of hexaborane(10), in which the osmium center is situated at the base of the pentagonal pyramid geometry. In a different synthetic protocol, we have carried out the metathesis reaction of [Cp*OsBr2]2 (Cp* = η5-pentamethylcyclopentadienyl), 5 with [LiBH4·THF] followed by thermolysis in the presence of [BH3·THF] that generated [Cp*Os(η5-B5H10)], 6. Cluster 6 has a planar pentaborane ring that is stabilized in the coordination sphere of osmium, making it a boron analogue of osmocene. Clusters 2 and 6 are the first examples of structurally characterized planar B4 and B5 rings, respectively, that are stabilized in the coordination sphere of osmium. All the synthesized molecules were characterized using multinuclear NMR and IR spectroscopy, mass spectrometry, and single crystal X-ray diffraction analyses. Theoretical calculations were carried out to visualize the electronic structures and bonding scenarios in 2 and 6.

Synthesis and Characterization of Lithium Pyrocarbonate (Li2[C2O5]) and Lithium Hydrogen Pyrocarbonate (Li[HC2O5]).

The anhydrous pyrocarbonate and the first hydrogen pyrocarbonate Li[HC2O5] have been synthesized in a laser-heated diamond anvil cell at moderate pressures ( GPa). The structures of the two compounds have been obtained from single crystal X-ray diffraction data. Raman spectroscopy and DFT calculations have been employed to further characterize their structure-property relations. The present results significantly enlarge the group of inorganic pyrocarbonates by the discovery of the hydrogenated pyrocarbonate anion Li[HC2O5]-. In the structure of Li[HC2O5] there is a symmetric O-H-O arrangement at high pressures, which converts to a conventional O-H O hydrogen bond upon pressure release.

Three new members of the hakite series, Cu6(Cu4Me2+2)Sb4Se13: hakite-(Cd), hakite-(Fe) and hakite-(Zn) from the Bytíz deposit, uranium and base-metal Příbram ore district, Czech Republic

Abstract Hakite-(Cd), hakite-(Fe) and hakite-(Zn) are new minerals belonging to the tetrahedrite group and forming, along with hakite-(Hg), the hakite series. They have been discovered in samples collected from the Bytíz deposit, in the uranium and base-metal Příbram ore district, Central Bohemia, Czech Republic. They occur as anhedral grains, up to 300 μm in size, in a calcite gangue, associated with clausthalite, cadmoselite, hakite-(Hg) [for hakite-(Cd)], berzelianite, bukovite, bytízite, crookesite, chaméanite, eskebornite, příbramite, the not yet approved giraudite-(Hg) and giraudite-(Cu), hakite-(Hg), umangite, chalcopyrite, tetrahedrite-(Zn) and a new Cu–As selenide [for hakite-(Fe) and -(Zn)]. The three new species are black, with a metallic lustre. Mohs hardness is ca. 3½–4; calculated density is 6.019 (Hak-Cd), 6.011 (Hak-Fe) and 6.081 g.cm–3 (Hak-Zn). In reflected light, they are isotropic, pale grey with bluish (Hak-Cd) or brownish (Hak-Fe and Hak-Zn) shades. Empirical formulae of hakite-(Cd), hakite-(Fe), and hakite-(Zn) are Cu9.71Ag0.24Cd1.51Hg0.43Zn0.03(Sb3.94As0.13)Σ4.07Se11.35S1.57, Cu10.11Ag0.18Fe0.81Zn0.50Hg0.26(Sb3.72As0.41)Σ4.13Se12.65S0.12, and Cu10.03Ag0.24Zn0.61Fe0.53Hg0.45(Sb3.55As0.60)Σ4.15Se12.82S0.08, respectively. These formulae correspond to the end-member formulae Cu6(Cu4Cd2)Sb4Se13 (Hak-Cd), Cu6(Cu4Fe2)Sb4Se13 (Hak-Fe), and Cu6(Cu4Zn2)Sb4Se13 (Hak-Zn). All these new members of the hakite series are cubic, I $\bar{4}$ 3m, Z = 2, with unit-cell parameters a = 10.8860(6) Å, V = 1290.0(2) Å3 (Hak-Cd); a = 10.7983(4) Å, V = 1259.12(14) Å3 (Hak-Fe); and a = 10.8116(14) Å, V = 1263.8(5) Å3 (Hak-Zn). These species are isotypic with the other members of the tetrahedrite group, and their crystal structures have been refined on the basis of single-crystal X-ray diffraction data down to R1 values of 0.0230 (Hak-Cd), 0.0254 (Hak-Fe), and 0.0302 (Hak-Zn). These structural data allow us to describe the S-to-Se partitioning in hakite-series minerals and to understand the mechanisms avoiding too short Me–Se distances in these selenides.

Enzyme (α-Glucosidase, α-Amylase, PTP1B & VEGFR-2) Inhibition and Cytotoxicity of Fluorinated Benzenesulfonic Ester Derivatives of the 5-Substituted 2-Hydroxy-3-nitroacetophenones

The prevalence of small multi-target drugs containing a fluorinated aromatic moiety among approved drugs in the market is due to the unique properties of this halogen atom. With the aim to develop potent antidiabetic agents, a series of phenylsulfonic esters based on the conjugation of the 5-substituted 2-hydroxy-3-nitroacetophenones 1a–d with phenylsulfonyl chloride derivatives substituted with a fluorine atom or fluorine-containing (-CF3 or -OCF3) group were prepared. Their structures were characterized using a combination of spectroscopic techniques complemented with a single-crystal X-ray diffraction (XRD) analysis on a representative example. The compounds were, in turn, assayed for inhibitory effect against α-glucosidase, α-amylase, protein tyrosine phosphatase 1 B (PTP1B) and the vascular endothelial growth factor receptor-2 (VEGFR-2) all of which are associated with the pathogenesis and progression of type 2 diabetes mellitus (T2DM). The antigrowth effect of selected compounds was evaluated on the human breast (MCF-7) and lung (A549) cancer cell lines. The compounds were also evaluated for cytotoxicity against the African Green Monkey kidney (Vero) cell line. The results of an in vitro enzymatic study were augmented by molecular docking (in silico) analysis. Their ADME (absorption, distribution, metabolism and excretion) properties have been evaluated on the most active compounds against α-glucosidase and/or α-amylase to predict their drug likeness.