Effects Of Halogen Substituents Research Articles

Effect of Halogen Substituents on Charge Transport Properties of n-type Organic Semiconductors: A Theoretical Study.

Organic semiconductors (OSCs) have received significant attention as promising materials for electronic devices. In this study, we investigate the impact of halogen groups on the charge transport properties of n-type OSC-6,13 bis((triisopropylsilyl)ethynyl)-5,7,12,14-tetraazapentacene (TIPS-TAP). The computed mobilities for TIPS-TAPs substituted with F and Cl exhibit excellent agreement with the experimental values, while the simulation overestimates the electron mobility for TIPS-TAP. Interestingly, the mobility of TIPS-TAP-4F is significantly lower than that of TIPS-TAP-4Cl/Br, despite their similar packing structures. This discrepancy can be attributed to the strong electron-withdrawing effect of fluoride, which reduces the electron transfer integral and increases the reorganization energy. While molecular packing is widely recognized as a dominant factor in charge transport in OSCs, our study highlights the crucial role of electronic effects in charge transport in OSCs. This study provides new insights into the mechanisms underlying charge transport in OSCs.

Photochemical degradation of bisphenol S and its tetrahalogenated derivatives in water

Bisphenol S (BPS), a widely used plasticizer, is known to have potential endocrine disrupting effects to organisms. Its tetrahalogenated derivatives, tetrachlorobisphenol S (TCBPS) and tetrabromobisphenol S (TBBPS), are flame retardants exhibiting high neurodevelopmental toxicity and cytotoxicity. Halogen substitution has been shown to significantly affect the optical and photochemical properties of organic compounds. In this study, we conducted a comparative investigation into the photochemical behaviors of BPS, TCBPS, and TBBPS in aqueous solutions under both laboratory UV and natural sunlight irradiation. Spectroscopic titration results indicated that the pKa of TCBPS (4.16) and TBBPS (4.13) are approximately 3.7 units smaller than that of BPS (7.85), indicating that the halogenated derivatives are mainly present as the phenolate anions under circumneutral conditions. The halogen substituents also cause a significant bathochromic shift in the absorption spectra of TCBPS and TBBPS compared to BPS, leading to the enhanced absorption of sunlight. Meanwhile, TCBPS and TBBPS showed higher quantum yields than BPS, attributed to the "heavy atom" effect of halogen substituents. GCSOLAR modeling predicted half-lives for BPS, TCBPS, and TBBPS in surface water in Nanjing (32°2′7.3′′N, 118°50′21′′E) under noon sunlight in clear mid-autumn days as 810.2, 3.4, and 0.7 min, respectively. Toxicity evaluation suggest potential ecological risks of BPS/TCBPS/TBBPS and their photoproducts to aquatic organisms. Our findings highlight direct photolysis as an important mechanism accounting for the attenuation of tetrahalogenated bisphenols in both sunlit surface waters and UV based water treatment processes.engineered (e.g., UV disinfection) and natural aquatic environments (e.g., surface fresh waters).

Unified chemical synthesis of cephalotaxus diterpenoids: A biosynthetic reversed strategy

In this work, we present the details of the first unified chemical synthesis of cephalotaxus diterpenoids with three distinct carbon skeleton structures. Drawing on our previous synthesis of cephalotane-type C18 dinorditerpenoid and inspired by the proposed biosynthetic synthesis pathway, we formulated a biosynthetic reversed chemical synthetic strategy. This strategy facilitated the conversion of C18 dinorditerpenoid into troponoid-type C19 norditerpenoid and intact cephalotane-type C20 diterpenoid through pivotal one-carbon introduction and ring expansion reactions. In the synthesis of troponoid-type C19 norditerpenoid, we utilized TMSCHN2 as one-carbon unit and meticulously examined the selective regulatory effect of halogen substituents in ring expansion and rearrangement reactions. This endeavor culminated in the successful synthesis of natural product molecules within this subclass, notably including cephinoid H and fortalpinoid C, marking the first chemical total synthesis in this line of research. In the investigation of intact cephalotane-type C20 diterpenoid synthesis, while adhering to the overall synthesis strategy, we initially pursued a ring expansion before carbon introduction approach, which proved unsuccessful. Subsequently, we explored a synthetic route of introducing carbon first and then expanding the ring, leading to a successful outcome and resulting in the first chemical total synthesis of the representative molecule cephanolide E within this subclass. Various challenges such as establishing crucial quaternary carbon stereocenters, selecting appropriate one-carbon units, and controlling ring expansion reactions were effectively addressed throughout this process. Moreover, enantioselective synthesis of natural products within this family was achieved through the development of asymmetric Michael reactions.

Transforming Thermally Activated Delayed Fluorescence to Room-Temperature Phosphorescence through Modulation of the Donor in Charge-Transfer Cocrystals.

A cocrystallization strategy is used through incorporation of 1,2,4,5-tetracyanobenzene (TCNB) as an acceptor with halogen-substituent thioxanthone (TX) derivatives as donors. The resulting cocrystals TT-R (R = H, F, Cl, Br, or I) transform the thermally activated delayed fluorescence emission in the TT-H, TT-F, and TT-Cl cocrystals to room-temperature phosphorescence in the TT-Br and TT-I cocrystals. Definite crystal packing structures demonstrate a 1:1 alternative donor-acceptor stacking in the TT-H cocrystal, a 2:1 alternative donor-acceptor stacking in the TT-F and TT-Cl cocrystals, and a separate stacking of donor and acceptor in the TT-Br and TT-I cocrystals. A transformation law can be revealed that with an increase in atomic number from H, F, Cl, Br, to I, the cocrystals show the structural transformation of the number of aggregated TX-R molecules from monomers to dimers and finally to multimers. This work will facilitate an understanding of the effect of halogen substituents on the crystal packing structure and luminescence properties in the cocrystals.

Effects of halogen atom substitution on luminescent radicals: a case study on tris(2,4,6-trichlorophenyl)methyl radical-carbazole dyads.

A series of halogen-substitute carbazole TTM radicals was synthesized. The effect of halogen substituents on radical luminescence was systematically evaluated. It was found that the well-known heavy atom effect does not work in the emission of radicals and that halogen substitution of the donor carbazole can change the HOMO and alter the absorption and emission wavelengths. In addition, the photostability was found to be improved with respect to TTM but not significantly different from that of closed-shell fluorescent molecules.

Solvent-free MeSO3H-promoted cyclotrimerization of acetophenones, effects of halogen and methoxy substituents on the reaction

Solvent-free MeSO3H-promoted cyclotrimerization of acetophenones, effects of halogen and methoxy substituents on the reaction

Formation of halogenated chloroxylenols through chlorination and their photochemical activity.

Trace organic contaminants usually go through multiple treatment units in a modern water treatment train. Structural modification triggered by pretreatment (e.g., prechlorination) may influence the further transformation and fate of contaminants in downstream units. However, knowledge on this aspect is still limited. In this contribution, we investigated the chlorination of chloroxylenol (PCMX), an antimicrobial agent extensively used during COVID-19 pandemic, and the photoreactivity of its halogenated derivatives. Results indicate that chlorination of PCMX mainly proceeded through electrophilic substitution to give chlorinated products, including Cl- and 2Cl-PCMX. The presence of bromide (Br-) resulted in brominated analogues. Owing to the bathochromic and "heavy atom" effects of halogen substituents, these products show increased light absorption and photoreactivity. Toxicity evaluation suggest that these halo-derivatives have higher persistence, bioaccumulation, and toxicity (PBT) than the parent PCMX. Results of this contribution advance our understanding of the transformation of PCMX during chlorination and the photochemical activity of its halogenated derivatives in subsequent UV disinfection process or sunlit surface waters.

Adsorption dynamics of benzene derivatives onto the surface of hydroxylated silica upon photoexcitation: Effect of halogen and methyl substituents

Adsorption of toxic substances is an important research field. In this work, the adsorption dynamics of halogenated and methylated benzenes onto hydroxylated silica upon photoexcitation has been investigated theoretically. The intermolecular interaction between the hydroxy (OH) group and the π electron density at the center of the benzene ring was also a major subject. In the ground state, the order of calculated adsorption energy was consistent with the OH⋅⋅⋅C bond strengths (SiO2–MeBe > SiO2–DimeBe > SiO2–BrBe > SiO2–ClBe > SiO2–FBe > SiO2–Be), implying this bond to be the major contributor to the adsorption. Upon photoexcitation to the first excited (S1) state by adsorbing shortwave-ultraviolet (UV), the OH⋅⋅⋅C bonds in each complex were strengthened with only the order of the bond strengths of SiO2–DimeBe and SiO2–MeBe reversed relative to the order in the ground state. In contrast to OH⋅⋅⋅C bonds, the OH⋅⋅⋅π bonds were all indicated to weaken upon photoexcitation. The results showed that the order of OH⋅⋅⋅π bond strengths in the S1 state to be SiO2–FBe > SiO2–BrBe > SiO2–DimeBe > SiO2–Be > SiO2–ClBe > SiO2–MeBe. However, the change in the corresponding adsorption energy was inconsistent with the order of OH⋅⋅⋅C bond strengths in the S1 state, due to the degree of weakening of the OH⋅⋅⋅π bond being greater than the degree of strengthening of the OH⋅⋅⋅C bonds. These changes were concluded to be induced by local excitation for each of the six complexes. This work has presented the photophysical dynamics of an adsorbent before and after photoexcitation.

Impacts of Halogen Substitutions on Bisphenol A Compounds Interaction with Human Serum Albumin: Exploring from Spectroscopic Techniques and Computer Simulations.

Bisphenol A (BPA) is an endocrine-disrupting compound, and the binding mechanism of BPA with carrier proteins has drawn widespread attention. Halogen substitutions can significantly impact the properties of BPA, resulting in various effects for human health. Here, we selected tetrabromobisphenol A (TBBPA) and tetrachlorobisphenol A (TCBPA) to investigate the interaction between different halogen-substituted BPAs and human serum albumin (HSA). TBBPA/TCBPA spontaneously occupied site I and formed stable binary complexes with HSA. Compared to TCBPA, TBBPA has higher binding affinity to HSA. The effect of different halogen substituents on the negatively charged surface area of BPA was an important reason for the higher binding affinity of TBBPA to HSA compared to TCBPA. Hydrogen bonds and van der Waals forces were crucial in the TCBPA-HSA complex, while the main driving factor for the formation of the TBBPA-HSA complex was hydrophobic interactions. Moreover, the presence of TBBPA/TCBPA changed the secondary structure of HSA. Amino acid residues such as Lys199, Lys195, Phe211, Arg218, His242, Leu481, and Trp214 were found to play crucial roles in the binding process between BPA compounds and HSA. Furthermore, the presence of halogen substituents facilitated the binding of BPA compounds with HSA.

Complexes of carbon dioxide with methanol and its monohalogen-substituted: Beyond the tetrel bond

This work aims to investigate a significant change in the bonding feature of CO2 complexes that turns from the C∙∙∙O tetrel bond to the OH∙∙∙O hydrogen one due to the effect of halogen-substitution into methanol. The behavior and bonding nature of noncovalent interactions are thoroughly analyzed and discussed. The binding energies were calculated at various methods and extrapolated to the CCSD(T)/CBS. Among DFT-based methods, the B3LYP-D3 is incredibly effective in calculating the binding energy of CH2XOH-CO2 (X = F, Cl, Br) complexes. This work would provide insight into the effect of halogen substituents on the bonding characteristics of noncovalent interactions.

Effect of halogen substituents on polymer membrane hydrophobicity, swelling and transport mechanism: chlorine versus fluorine

While the role of fluorine on mass transport in polymers has been the subject of extensive research efforts, less attention has been paid to the role played by other halogens, such as chlorine. These efforts favored the synthesis of a plethora of perfluoropolymers which, although exhibiting enhanced physical aging resistance relative to conventional hydrocarbon-based polymers, suffer from swelling and plasticization in the presence of hydrocarbons.In this study, we show that the presence of chlorine in perfluoropolymers alters their hydrophobicity while enhancing swelling resistance and size-sieving ability. Model polar vapors, such as methanol and water, and non-polar hydrocarbon vapors were selected for a fundamental transport study in a series of co-polymers of perfluoro(2-methylene-4-methyl-1,3-dioxolane (PFMMD) and chlorotrifluoroethylene (CTFE), namely poly(PFMMD-co-CTFE), exhibiting systematically varied molar amount of CTFE (i.e., chlorine). Fundamental structure-property correlations were developed and possible applications in the field of membrane separations were outlined. Finally, a series of solubility data of chlorinated fluids in polar liquids was discussed to support our conclusions.

Effect of halogen substituents on the intermolecular interactions and magnetic properties of Mn(III) complexes

Six mononuclear Mn(III) complexes with hexadentate Schiff-base ligand, the products of the reaction between a N,N′-bis(3-aminopropyl)ethylenediamine or triethylenetetramine and 5-X-salicylaldehyde have been synthesized: the I− salts of complexes 1–3 exhibit a gradual SCO behavior, [Mn(5-Cl-sal-N-1,5,8,12)]I (1) shows a nearly complete SCO with T1/2 = 125 K, whereas [Mn(5-Br-sal-N-1,5,8,12)]I (2) and [Mn(5-I-sal-N-1,5,8,12)]I (3) show a gradual and incomplete SCO above room temperature. [Mn(5-F-sal-N-1,4,7,10)]I (4) predominantly remains HS state at all temperatures. [Mn(5-I-sal-N-1,5,8,12)]NO3 (5) and [Mn(5-F-sal-N-1,5,8,12)]NO3 (6) show an almost full conversion to the HS state and a more gradual SCO having the T1/2 value of 282 K for 5 and 159 K for 6, respectively.

Quantitative identification of halo-methyl-benzoquinones as disinfection byproducts in drinking water using a pseudo-targeted LC-MS/MS method

Halobenzoquinones (HBQs) as disinfection byproducts (DBPs) in drinking water is prioritized for research due to their prevalent occurrence and high toxicity. However, only fifteen HBQs can be identified among a high diversity using targeted LC-MS/MS analysis in previous studies due to the lack of chemical standards. In this study, we developed a pseudo-targeted LC-MS/MS method for detecting and quantifying diverse HBQs. Distinct fragment characteristics of HBQs was observed according to the halogen substituent effects, and extended to the development of a multiple-reaction-monitoring (MRM) method for the quantification of the 46 HBQs that were observed in simulated drinking water using non-targeted analysis. The fragmentation mechanism was supported by the changes of Gibbs free energy (ΔG), and a linear relationship between the ΔG and the ionization efficiency of analytes was developed accordingly for quantification of these 46 HBQs, 30 of which were lack of chemical standards. It is noted that 29 of the 30 newly-identified HBQs were halo-methyl-benzoquinones (HMBQs), which were predicted to be carcinogens related with drinking-water bladder cancer risk and be more toxic than non-methyl HBQs. Using the new method, twelve HMBQs were detected in actual drinking water samples with concentrations up to 100.4 ng/L, 3 times higher than that reported previously. The cytotoxicity in CHO cells of HMBQs was over 1-fold higher than that of non-methyl-HBQs. Therefore, HMBQs are an essential, highly toxic group of HBQs in drinking water, which deserve particular monitoring and control.

The effects of halogen substituents on structure, stability, and electronic properties of bicyclo[1.1.1]pentanylene at density functional theory

AbstractIn a quest to identify novel bicyclic carbenes, the effects of halogen substituents on the stability and reactivity of singlet (s) and triplet (t) forms of carbenes with one, two, and three carbenic centers (1‐15) are compared and contrasted, at B3LYP/6‐311++G** level of theory. All carbene scrutinized turn out as minima for showing no negative force constant on their energy surfaces. The highest stability (ΔEs‐t) and band gap (ΔEHOMO–LUMO) belongs to carbene 11 (37.36 and 133.45 kcal/mol, respectively) with three carbenic centers. Such higher stabilization attributed to three coordinate covalent bonds with their carbenic centers. The nucleophilicity (N) for each series (1‐5, 6‐10, and 11‐15) appears inverse correlation with our results of chemical potential (μ) values. Also, the N of the carbenic center is decreased due to the higher electronegativity of substituted halogens. In addition, the electrostatic potential (ESP) maps qualitatively confirm the relative N for our bicyclic carbenes.The aim of the present work was to assess the effects of halogen substituents on the stability (ΔEs‐t), ΔΕHOMO–LUMO, N, electrophilicity (ω), and proton affinity (ΔEPA). Finally, our investigation introduces carbene 1s with high stability (ΔEs‐t = 30.38 kcal/mol), N (3.438 eV), and negative ΔEPA (−244.94 kcal/mol) that can be applied as accumulated multidentate ligands.

Investigating phosphorescence capability of halogen-substituted metal-free organic molecules: A theoretical study

The radiative and non-radiative decay processes of five compounds are investigated through a comprehensive computational approach, for the aim of investigating the effect of different halogen substituents to the phosphorescent emission. Their optimal configurations at the ground (S0) and lowest triplet excited (T1) states are obtained and the calculated phosphorescent emission spectra are comparable with the experimental values. For 1,4-di(9H-carbazol-9-yl)benzene (PDCz), the electronic transition is between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), while for the four halides, the electronic transitions are attributed to several molecular orbitals. According to calculations, 9,9′-(2,5-diiodo-1,4-phenylene)bis(9H-carbazole) (PDICz) possesses the largest radiative decay rate constant (kr) and non-radiative decay rate constant (knr), which can be attributed to the strong spin-orbital coupling from the heavy iodine atom. However, the phosphorescent quantum efficiency (Φ) of PDICz is lower than that of 9,9′-(2,5-dibromo-1,4-phenylene)bis(9H-carbazole) (PDBCz), implying that a comprehensive consideration is necessary. Furthermore, by analyzing the vibrational mode, we have confirmed that the reorganization energies are also influenced by the different halogen atoms. While the dominated factor that determines the kr and knr comes from the spin-orbital coupling. We expect that our research findings will be beneficial to the newly designed organic phosphorescent materials in the future.

Probing the Effect of Halogen Substituents (Br, Cl, and F) on the Non-covalent Interactions in 1-(Adamantan-1-yl)-3-arylthiourea Derivatives: A Theoretical Study.

The effect of halogen substituents (X = Br, Cl, and F) on the crystal packing and intra- and intermolecular interactions in four adamantane–thiourea hybrid derivatives is investigated using different theoretical tools. The bromo and chloro derivatives exhibit 3D isostructurality as evident from lattice parameters, molecular conformation, and crystal packing. The density functional theory study suggests that the molecular conformation of the parent (unsubstituted) and fluoro derivatives exhibits a stable low energy anti–syn conformation. In contrast, bromo and chloro derivatives adopt stable and relatively high energy minima on their potential energy surfaces. Hirshfeld surface analysis reveals the effect of halogen substituents on the intermolecular contacts. The halogen atoms mainly reduce the contribution of H···H contacts toward crystal packing. PIXEL energy analysis indicates the strong dimer formed by N–H···S hydrogen bonds in all four structures. It also revealed that a vast number of H···H contacts observed in different dimers of these structures either presented along with other conventional interactions or solely stabilize the dimeric topology. The topological parameters for intermolecular interactions in these structures suggest an intermediate bonding character between shared and closed-shell interactions for N–H···S hydrogen bonds in the parent and chloro derivatives. In contrast, the N–H···S hydrogen bond in other structures is of a closed-shell interaction. Among four derivatives, the fluoro derivative is weakly packed in the solid state based on the PIXEL method’s lattice energy calculation.

Copper(ii) complexes with tridentate halogen-substituted Schiff base ligands: synthesis, crystal structures and investigating the effect of halogenation, leaving groups and ligand flexibility on antiproliferative activities.

To investigate the effect of different halogen substituents and leaving groups and the flexibility of ligands on the anticancer activity of copper complexes, sixteen copper(ii) complexes with eight different tridentate Schiff-base ligands containing pyridine and 3,5-halogen-substituted phenol moieties were synthesized and characterized by spectroscopic methods. Four of these complexes were also characterized by X-ray crystallography. The cytotoxicity of the complexes was determined in three different tumor cell lines (i.e. the A2780 ovarian, HCT116 colorectal and MCF7 breast cancer cell line) and in a normal primary fibroblast cell line. Complexes were demonstrated to induce a higher loss of cell viability in the ovarian carcinoma cell line (A2780) with respect to the other two tumor cell lines, and therefore the biological mechanisms underlying this loss of viability were further investigated. Complexes with ligand L1 (containing a 2-pycolylamine-type motif) were more cytotoxic than complexes with L2 (containing a 2-(2-pyridyl)ethylamine-type motif). The loss of cell viability in A2780 tumor cells was observed in the order Cu(Cl2-L1)NO3 > Cu(Cl2-L1)Cl > Cu(Br2-L1)Cl > Cu(BrCl-L1)Cl. All complexes were able to induce reactive oxygen species (ROS) that could be related to the loss of cell viability. Complexes Cu(BrCl-L1)Cl and Cu(Cl2-L1)NO3 were able to promote A2780 cell apoptosis and autophagy and for complex Cu(BrCl-L1)Cl the increase in apoptosis was due to the intrinsic pathway. Cu(Cl2-L1)Cl and Cu(Br2-L1)Cl complexes lead to cellular detachment allowing to correlate with the results of loss of cell viability. Despite the ability of the Cu(BrCl-L1)Cl complex to induce programmed cell death in A2780 cells, its therapeutic window turned out to be low making the Cu(Cl2-L1)NO3 complex the most promising candidate for additional biological applications.

Heteroleptic enantiopure Pd(ii)-complexes derived from halogen-substituted Schiff bases and 2-picolylamine: synthesis, experimental and computational characterization and investigation of the influence of chirality and halogen atoms on the anticancer activity

To investigate the effect of chirality and different halogen substituents on the anticancer activity, seven enantiomeric pairs of palladium complexes were synthesized and characterized.

X-ray and theoretical investigation of (Z)-3-(adamantan-1-yl)-1-(phenyl or 3-chlorophenyl)-S-(4-bromobenzyl)isothioureas: an exploration involving weak non-covalent interactions, chemotherapeutic activities and QM/MM binding energy

A detailed exploration of crystal packing of two adamantane-isothiourea hybrid derivatives along with a known closely related structure has been performed to delineate the effect of halogen substituents and the role of weak intermolecular interactions in their supramolecular architectures. The adamantane-isothiourea hybrid derivatives used in the present study are (Z)-3-(Adamantan-1-yl)-S-(4-bromobenzyl)-1-phenylisothiourea (1), C24H27BrN2S and (Z)-3-(Adamantan-1-yl)-S-(4-bromobenzyl)-1-(3-chlorophenyl)isothiourea (2), C24H26BrClN2S, characterized by X-ray crystallography. The X-ray structures revealed that the molecular conformation of 1 and 2 are different and stabilized by intramolecular C–H···N interactions. In addition, a short intramolecular H···H contact is formed in 2. The Hirshfeld surface analysis was used to delineate the nature of different intermolecular interactions and their contributions toward crystal packing. The quantitative analysis of strengths of molecular dimers existed in 1 and 2 has been performed using the PIXEL method. The electrostatic potential map clearly revealed nature and strength of σ-holes at Br and Cl atoms. The topological analysis was used to characterize the nature and the strength of various intermolecular interactions including the type I Br···Br contact. Interestingly, all the H–H bonding observed in 1 and 2 show closed-shell in nature. Further, an in-vitro antimicrobial activity studies suggest that the title compounds exhibited potent antibacterial activity against all the tested Gram-positive bacterial strains and Gram-negative Escherichia coli. Compound 2 showed marked anti-proliferative activity against MCF-7 and HeLa cell lines. Communicated by Ramaswamy H. Sarma

Antiproliferative Activities of Diimine-Based Mixed Ligand Copper(II) Complexes.

A series of Cu(diimine)(X-sal)(NO3) complexes, where the diimine is either 2,2'-bipyridine (bpy) or 1,10-phenanthroline (phen) and X-sal is a monoanionic halogenated salicylaldehyde (X = Cl, Br, I, or H), have been synthesized and characterized by elemental analysis and X-ray crystallography. Penta-coordinate geometries copper(II) were observed for all cases. The influence of the diimine coligands and different halogen atoms on the antiproliferative activities toward human cancer cell lines have been investigated. All Cu(II) complexes were able to induce a loss of A2780 ovarian carcinoma cell viability, with phen derivatives more active than bpy derivatives. In contrast, no in vitro antiproliferative effects were observed against the HCT116 colorectal cancer cell line. These cytotoxicity differences were not due to a different intracellular concentration of the complexes determined by inductively coupled plasma atomic emission spectroscopy. A small effect of different halogen substituents on the phenolic ring was observed, with X = Cl being the most highly active toward A2780 cells among the phen derivatives, while X = Br presented the lowest IC50 in A2780 cells for bpy analogs. Importantly, no reduction in normal primary fibroblasts cell viability was observed in the presence of bpy derivatives (IC50 > 40 μM). Mechanistically, complex 1 seems to induce a stronger apoptotic response with a higher increase in mitochondrial membrane depolarization and an increased level of intracellular reactive oxygen species (ROS) compared to complex 3. Together, these data and the low IC50 compared to cisplatin in A2780 ovarian carcinoma cell line demonstrate the potential of these bpy derivatives for further in vivo studies.