Intramolecular Charge Transfer Interactions Research Articles

Acyl hydrazone-based reversible optical switch for reporting of cyanide ion in industrial wastewater samples

The anion binding property of a series of easily synthesizable, isonicotine acid hydrazide based optical switches were studied in the semi-aqueous environment. Irrespective to the position of the hydrazide units, all three compounds show color change (as well as turn-off fluorescence response) with CN− ion, presumably due to hydrogen bonding triggered intramolecular charge transfer interaction. The compound with phenanthroline as the signaling unit, shows effective E Z isomerization with substantial amount of kinetically stable Z-isomer in the equilibrium, stabilized by intramolecular hydrogen bonding. This compound showed a 1:1 binding interaction with CN− ion due to its ‘U’ shaped conformation. On the other hand, compound with two isoniazid hydrazide moieties at 1,4-positions, shows 1:2 interaction with CN− ions. Further, the probe molecules were utilized for the detection of CN− ions in water samples collected from different natural resources. Low-cost portable optical kit based on reusable paper strips were designed for rapid, on-location detection purpose.

An ultrasensitive fluorescent breath ammonia sensor for noninvasive diagnosis of chronic kidney disease and helicobacter pylori infection

Breath ammonia detection has been a significant non-invasive approach for disease diagnosis. However, the reported methods for breath ammonia detection suffer from high cost, time-consuming, complex operation, or low selectivity. Fluorescence analysis as an alternative method has not been introduced in the detection of breath ammonia due to its insufficient sensitivity. In this work, a rationally designed strategy is proposed to improve the sensitivity of fluorescence sensors by increasing the amount of recognition site and enhancing the brightness of the solid-state fluorescence in sensor molecule. Briefly, three curcumin (CUR) derivatives BFCUR, MBFCUR and MBFCURM with D-π-A-π-D conjugated system were synthesized. Compared with the other two control molecules MBFCUR and MBFCURM, whose phenol groups at one or both ends of BFCUR were protected by a methyl group, BFCUR has two response sites, thus, two intramolecular charge transfer (ICT) interactions occurred after exposure to ammonia, suggesting the improved sensitivity. Moreover, the large steric hindrance of boron trifluoride in BFCUR can prevent the π-π stacking of molecules and endow BFCUR with bright solid-state fluorescence. BFCUR was subsequently loaded into electrospun nanofibers (ENFs) with high specific surface area, which further improved the detection sensitivity. The obtained BFCUR-loaded ENFs sensor (denoted as BFCUR-ENF) exhibited ultra-low LOD of 22 ppb for ammonia. BFCUR-ENF is successfully applied to breath ammonia detection in healthy volunteers, patients with chronic kidney disease (CKD) and Helicobacter pylori (H. pylori) infection, demonstrating its great application potentials. Taken together, the first fluorescent sensor for breath ammonia detection was successfully constructed for noninvasive diagnosis of CKD and H. pylori.

Synthesis of Crystalline Fluoro-Functionalized Imines, Single Crystal Investigation, Hirshfeld Surface Analysis, and Theoretical Exploration.

This investigation is focused on the synthesis of two halo-functionalized crystalline Schiff base (imine) compounds: (E)-2-methoxy-6-(((3-(trifluoromethyl)phenyl)imino)methyl)phenol (MFIP) and (E)-1-(((2-fluorophenyl)imino)methyl)naphthalen-2-ol (FPIN) by the condensation reaction of substituted benzaldehydes and substituted aniline. The crystal structures of MFIP and FPIN were determined unambiguously by single-crystal X-ray diffraction (SC-XRD) studies. Intermolecular interactions and the role of fluorine atoms in the stabilization of the crystal packing are explored for both compounds using Hirshfeld surface analysis. Accompanied with experimental studies, quantum chemical calculations were also performed for comprehensive structure elucidation at the M06/6-311G(d,p) level of theory. A comparison of experimental and density functional theory results for geometrical parameters exhibited excellent agreement. Interestingly, Frontier molecular orbitals and natural bond orbital (NBO) findings revealed that intramolecular charge transfer and hyper-conjugation interactions had played a significant role to stabilize the molecules. Both compounds exhibited a relatively larger value of hardness with a smaller global softness, which, as proposed by the SC-XRD and NBO study, shows a higher stability. Nonlinear optical (NLO) findings showed that FPIN manifested a larger value of linear polarizability (<a> = 293.06 a.u.) and second-order hyperpolarizability (<γ> = 3.31 × 105 a.u.) than MFIP (<a> = 252.42 and <γ> = 2.08 × 105 a.u.) due to an extended conjugation. The above-mentioned findings of the entitled compounds may play a crucial role in NLO applications.

K+ Ion-Doped Mixed Carbon Nitride: A Daylight-Driven Photocatalyst and Luminophore for Enhanced Chemiluminescence.

Photocatalytic production of reactive oxygen species from O2 at the interface of the photocatalyst is significant to convert luminous energy like daylight into chemical energy and could be momentous for a reactive oxygen species-based chemiluminescence system. Herein, we synthesized a novel K+ ion-doped tri-s-triazine/triazine mixed carbon nitride (MCN), in which K+ ions were intercalated into the layers in a bridging manner. After a mild daylight treatment for 30 min, the MCN suspension could produce long-lifetime reactive oxygen species and further directly produce intense and stable chemiluminescence emission in the presence of luminol. In particular, the chemiluminescence intensity was 780 times that of H2O2-luminol, and MCN could be recycled several times in the chemiluminescence system. The mechanism results revealed a large number of reactive oxygen species that were generated from O2 on the surface of MCN through a temperate photocatalytic process. In the theoretical calculation, the charge density of N interacting with K+ ions was significantly more negative than that at the corresponding position in graphitic carbon nitride, which was beneficial to the adsorption and activation of oxygen, and the narrower band gap suggested that the doping of K+ ions was conducive to the intramolecular charge transfer interaction. Then, the long-lifetime reactive oxygen species triggered the conversion of luminol into an excited-state intermediate, which further transferred energy to MCN, producing strong chemiluminescence emission. The K+ ion-doped MCN might conduct as an efficient photocatalyst for reactive oxygen species generation, recyclable catalysts, and luminophores in the photoinduced chemiluminescence system.

Synthesis, structural, vibrational, molecular docking and nonlinear optical studies of (E)-N′-(2,3-dimethoxybenzylidene)-4-fluorobenzohydrazide

Organic nonlinear optical single crystals of (E)-N′-(2,3-dimethoxybenzylidene)-4-fluorobenzohydrazide (DMB-FBH) were synthesized and grown using slow evaporation crystallization from ethanol solution. The single crystal X-ray diffraction scattering revealed that the DMB-FBH crystallised in the tetragonal crystal system with a centro symmetric space group of I 41/a. The crystallographic bond lengths and bond angles were compared with the values generated from optimized molecular geometry based on quantum chemical calculations. The functional group vibrations were identified theoretically by density functional theory with B3LYP 6–311 G (d,p) basis set using Gaussian 09 software package and their vibrations were compared with the experimental FT-IR spectra. The UV-visible and the fluorescence emission spectra of the DMB-FBH in aqueous solutions were recorded. The HOMO-LUMO energy level pictogram addressed the intramolecular charge transfer (ICT) interaction between donor and acceptor moieties and their impact on the energy gap was determined. Different interactions such as O···H, N···H, C···C and C···H in DMB-FBH were quantified via fingerprint plots and these results were compared with that of similar structure. The detailed molecular docking simulation was carried out with M. tuberculosis protein [PDB ID:2 × 22]. The third order nonlinear optical susceptibility (χ3) of DMB-FBH was confirmed experimentally by Z-scan method and their conversion efficiency was higher than the other hydrazones derivatives. In short, this work discusses the crystal structure, identification and quantification of the molecular interactions, thermal, antimycobacterial and optical properties of new hydrazone derivative.

Realization of Single-Phase White-Light-Emitting Materials with Time-Evolution Ultralong Room-Temperature Phosphorescence by Coordination Assemblies.

Two Cd-based supramolecular coordination polymers, [Cd3(CzIP)3(DMF)2] (1) and [Cd2(CzIP)2(DMF)4] (2), were synthesized by using 5-(carbazol-9-yl) isophthalate (CzIP) as ligands. These two compounds exhibit multiple luminescence emissions; apart from fluorescence, time- and temperature-dependent ultralong phosphorescence (RTP) were also achieved under room conditions. Significantly, compound 1 has a long-lived afterglow of 0.93 s at 545 nm under ambient conditions. Compound 2 shows nearly pure white-light emission with CIE coordinates of (0.33, 0.33) via the dual emission of fluorescence and phosphorescence. It has come to our attention that it is the first example of a luminescent coordination polymer with single-phase white-light emission and color-evolution RTP. In addition, the long-lived RTP materials can be used in time-dependent anticounterfeiting and white-light-emitting diodes. Experimental and singlet and triplet state calculations indicate that both C-H···π interaction and inter- and intramolecular charge transfer interactions could be beneficial to the emission of ultralong RTP.

Density functional theoretical study, spectroscopic characterization and molecular docking of the diuretic drug, spironolactone, adsorbed on AuNPs surface and in-vitro studies based on anticancer activity studies against A549 lung cancer cell line

In this study, the geometry, intramolecular charge transfer interactions, and harmonic vibrational frequencies of the diuretic drug, Spironolactone (SPL) and SPL adsorbed on gold nanoparticle (SPLA molecule) were investigated with the help of density functional theory method. Both molecules were found to be stabilized by intramolecular hydrogen bonds C7-H37. O27 and C16-H47. O2, as well as intramolecular charge transfer interactions. These interactions were quantitatively confirmed using natural localized molecular orbitals (NLMOs) analysis. The frontier molecular orbital analysis provided a comparative picture of the reactivity, showing a low value of the energy gap, revealing electron transport in the molecule. The most reactive sites of the molecules were predicted by the molecular electrostatic potential map analysis together with the study of local and global reactivity descriptors. FT-IR and Raman spectral analysis confirmed the existence of significant hydrogen bonding, and charge delocalization in the molecules. Molecular docking performed for the biological activity screening of both molecules along with the SERS and MTT assay (in vitro) analysis confirmed their cancer activity. All the comparative results lead to the conclusion that SPLA possess enhanced therapeutic activity than SPL and hence can be used for effective label-free monitoring of cells in-vitro.

Intramolecular-locked triphenylamine derivatives with adjustable room temperature phosphorescence properties by the substituent effect

A series of intramolecular-locked triphenylamine derivatives with adjustable room temperature phosphorescence properties by the substituent effect, which can tune the intramolecular charge transfer and intermolecular interactions.

Synthesis, characterization, DFT studies and molecular docking investigation of 2-oxo-ethyl piperidine pentanamide-derived sulfonamides as anti-diabetic agents

The present study is focused on the synthesis, characterization, DFT Studies, and in silico biological evaluation of novel benzenesulfonamides as antidiabetic agents. The compounds were synthesized and characterized experimentally using the NMR, FT-IR and HRMS while the molecular electronic structure properties were investigated using DFT-based theoretical methods at the M06-2X/6–311++G (d, p) level of theory. The results of the calculated vibrational energies were in perfect agreement with those of the experimental frequencies for different functional groups. The natural bond orbital (NBO) analysis was also carried out to study the intramolecular charge transfer interactions and energies of stabilization. Molecular docking simulation showed that the compounds; 3-Methyl-2-(4-methylphenylsulfonamido)-N-(2-oxo-2(piperidin-1-yl) ethyl) pentanamide (MMOPEP), 3-Methyl-N-(2-oxo-2-(piperidin-1-yl)ethyl))-2-(phenylsulfonamido)pentanamide (MOPEPP) and, 3-Methyl-2-(4-nitrophenylsulfonamido)-N-(2-oxo-2-(piperidin-1-yl)ethyl)pentanamide (MNOPEP) fitted tightly to the amino acid residues binding sites of insulin inhibiting protein receptors (7m17) with an average binding affinity of −6.9 kcal/mol, −6.6 kcal/mol, −6.7 kcal/mol respectively, thereby stimulating the release of insulin from functioning pancreatic beta cells which will in turn, lower blood glucose. This study provides a platform for scrutiny and clinical trials of benzenesulfonamide-based drugs as antidiabetic agents.

Carboxylato-Pillar[6]arene-Based Fluorescent Indicator Displacement Assays for Caffeine Sensing.

In the present work, we have developed a new indicator displacement system based on pillararene for anionic water-soluble carboxylato pillar [6] arene (WP6) and aromatic fluorescent dye safranine T (ST). A large fluorescence enhancement and colour change of ST were observed after complexation with electron-rich cavity in WP6 because of host-guest twisted intramolecular charge-transfer interactions. The constructed pillararene-indicator displacement system can be applied for caffeine selective detection in water.

Computational Calculation of Dissolved Organic Matter Absorption Spectra.

The absorption spectrum of dissolved organic matter (DOM) is a topic of interest to environmental scientists and engineers as it can be used to assess both the concentration and physicochemical properties of DOM. In this study, the UV-vis spectra for DOM model compounds were calculated using time-dependent density functional theory. Summing these individual spectra, it was possible to re-create the observed exponential shape of the DOM absorption spectra. Additionally, by predicting the effects of sodium borohydride reduction on the model compounds and then calculating the UV-vis absorbance spectra of the reduced compounds, it was also possible to correctly predict the effects of borohydride reduction on DOM absorbance spectra with a relatively larger decrease in absorbance at longer wavelengths. The contribution of charge-transfer (CT) interactions to DOM absorption was also evaluated, and the calculations showed that intra-molecular CT interactions could take place, while inter-molecular CT interactions were proposed to be less likely to contribute.

Stable Diarylamine-Substituted Tris(2,4,6-trichlorophenyl)methyl Radicals: One-Step Synthesis, Near-Infrared Emission, and Redox Chemistry

Stable Diarylamine-Substituted Tris(2,4,6-trichlorophenyl)methyl Radicals: One-Step Synthesis, Near-Infrared Emission, and Redox Chemistry

Ladder-Type Fused Benzodithiophene Extended along the Short-Axis Direction as a New Donor Building Block for Efficient Organic Solar Cells.

Ladder-type fused aromatic systems are important core structures of small molecule acceptors for organic solar cells (OSCs). In this study, a new ladder-type donor building block, based on the benzo[1,2-b:4,5-b']dithiophene (BDT) unit where the 3,7 positions of the BDT thiophene rings and the 3' position of the thiophene rings of the vertical BDT were fused to construct a seven-ring core structure named f-DTBDT, was investigated. In the f-DTBDT structure, the fusion of the BDT core and the thiophene rings at the 4,8 positions of BDT constrains all of the aromatic rings in a coplanar structure. The newly designed f-DTBDT was successfully employed as a core donor building block and conjugated with three electron-withdrawing acceptors (2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene) malononitrile (2HIC), 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2FIC), and 2-(5,6-dichloro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2ClIC)) as acceptor-donor-acceptor (A-D-A)-type acceptor materials for OSCs. Characterization results showed that the three synthesized A-D-A acceptors of DTBDT-IC, DTBDT-4F, and DTBDT-4Cl have high absorption behavior in the vis-NIR region as result of an intramolecular charge transfer interaction engendered by f-DTBDT and the ending group. The absorption regions of the acceptors were complementary with that of polymer PM6. Also, the frontier orbital energy levels of the new acceptors and wide-band-gap PM6 are well matched. Bulk heterojunction OSCs were fabricated using PM6 and the acceptors, and the highest power conversion efficiency (PCE) of 10.15% was obtained when using PM6:DTBDT-4F as the active layer.

Two-photon excited fluorescence from ground-state charge-transfer cocrystals of acridine and 1,2,4,5-tetracyano-benzene

Near-infrared two-photon absorption (TPA) molecules designed based on intramolecular charge-transfer (CT) interactions have been widely investigated during the last few decades; however, studies on supramolecular TPA materials based on intermolecular CT interactions are quite rare. In this work, cocrystals of acridine and 1,2,4,5-tetracyano-benzene were successfully prepared by self-assembly. The cocrystals show yellow emission centered at ∼540 nm with a solid-state photoluminescence quantum yields (PLQY) of 22.48%. Two-photon excited fluorescence (TPEF) measurements show that the cocrystals display wide-window TPEF that is absent in their individual components. Optical absorption analysis indicate that the fluorescence is originated from excitation from the ground states to CT exciton states instead of exciton states of donor or acceptor molecules. This work may facilitate further two-component nonlinear optical material design and applications.

Imidazole-Functionalized Y-Shaped Push-Pull Dye for Nerve Agent Sensing as well as a Catalyst for Their Detoxification.

A Y-shaped push-pull dye (1) with N,N-dimethylanilino donors and a benzonitrile acceptor connected via an imidazole-based π-conjugated spacer was designed. It showed a dark yellow color in solution due to facile intramolecular charge-transfer interaction, but no fluorescence was detected, presumably due to the photo-induced electron transfer effect of the imidazole moiety. However, addition of nerve agents such as diethyl chlorophosphate (DCP, sarin mimic) and diethyl cyanophosphate (DCNP, Tabun mimic) resulted in a blue-colored fluorescence with fading of the native dark yellow color. Mechanistic studies indicated nucleophilic attack of imidazole at the phosphorus of DCP or DCNP, leading to the formation of a phosphorylated intermediate, which undergoes time-dependent hydrolysis (∼24 h) in aqueous medium. This process recovers the free probe (enzyme-like behavior) and releases a less-toxic organophosphate compound as the byproduct. The phosphorylated derivative of 1, formed during such interaction, shows a different electronic behavior, which reduces the extent of charge-transfer interaction as well as nonradiative decay and supports emissive properties. Considering the high sensitivity of 1 towards DCP and DCNP with LOD 35 and 42 ppb, we prepared easy test strips for on-site vapor-phase detection of nerve agents.

Synthesis, crystal structure, spectroscopic characterization, α-glucosidase inhibition and computational studies of (E)-5-methyl-N′-(pyridin-2-ylmethylene)-1H-pyrazole-3-carbohydrazide

A new crystal, i.e, (E)-5-methyl-N′-(pyridin-2-ylmethylene)-1H-pyrazole-3-carbohydrazide (E-MPPC) has been synthesized and characterized by using FT-IR, UV-Vis, 1H-NMR, 13C-NMR, ESI-MS and single-crystal X-ray diffraction. In addition, a density functional theory study for the title compound was carried out. The theoretical geometry of the ground state and the electronic structure of the title compound were optimized by the DFT/B3LYP method in conjunction with 6-311++G(d,p) basis set. E-MPPC was evaluated in vitro for their α-glucosidase enzyme inhibition. The title compound displayed moderate inhibitory activity with IC50 value of 714.25 ± 8.33 µM against α-glucosidase enzyme. In addition, molecular docking study was performed to investigate how E-MPPC interacts with the protein structure of α-glucosidase enzyme. Final intermolecular energy and estimated inhibition constant for this docking study were obtained as -5.50 kcal/mol and 173.57 µM, respectively. The first order static hyperpolarizability (β) parameter for E-MPPC was also calculated as 11.2×10−30 esu. Natural bond orbital analysis was also executed to investigate intramolecular charge transfer interactions in the title compound.

Synthesis, structural, DFT and bio-assay of novel ethyl 3-(2-(4-chlorophenoxy)acetamido) propanoate on Galleria mellonela (wax moth) – a juvenile hormone mimic as potential insect growth regulator (IGR)

Ethyl 3-(2-(4-chlorophenoxy)acetamido)propanoate is synthesized and comprehensively studied as an insect growth regulator. The structure has been confirmed using fourier transform infra-red (FT-IR), nuclear magnetic resonance (1D-NMR, 2D-NMR), electrospray ionization (ESI-MS) spectroscopic techniques. The synthesized compound has been tested against the fifth instar of Galleria mellonella in comparison to pyriproxyfen (commercial IGR). Observed LC50 and LC90 values of synthesized compound and pyriproxyfen are 162 ppm & 549 ppm and 125 & 630 ppm respectively. Computational and structural parameters of the synthesized compound are determined and studied. Molecular geometry and unscaled vibrational frequencies are calculated by density functional theory (DFT) method using Becke's three-parameter lee-yang-parr (B3LYP) hybrid functional at 6–311G+(d,2p) level of basis set. The scaled quantum mechanical (SQM) method has been employed to calculate scaled vibrational frequencies. Further, 1H and 13C NMR spectra are calculated with (DFT/ B3LYP) using gage independent atomic orbital method (GIAO) in the gaseous and solvent phases to confirm the structure of synthesized compound. Natural bond orbital (NBO) analysis has been used to study the intramolecular charge transfer (ICT) interactions, delocalization of electron density. HOMO-LUMO energies are calculated to describe global reactivity descriptors which played an important role in explaining the bioactivity of compounds. Parameters are also evaluated in solvent phases using the integral equation formalism polarization continuum model (IEF-PCM) of the DFT method. The Autodock software tool is used to study the binding interactions between ligand and receptor juvenile hormone binding protein (JHBP).

Synthesis, Structures, and Electronic Properties of 2,7-Anthrylene-Based Azacyclophanes Bearing o-, m-, and p-Phenylenediamine Linkers.

A series of novel azacyclophanes consisting of 2,7-anthrylene and phenylene units were designed and synthesized by the Buchwald-Hartwig coupling reaction to investigate their unique electronic properties in multiple oxidized states. Cyclic voltammetry showed that the p-phenylene derivative exhibited three reversible oxidation waves, whereas the o- and m-phenylene derivatives showed two quasi-reversible oxidation waves due to the complicated intramolecular interaction between the oxidized units and neutral units. Moreover, the absorption spectra of the p-phenylene derivative in different oxidation states showed absorption bands at 865 and 1025 nm, which were attributed to intramolecular charge-transfer interactions. The photophysical and electrochemical properties of the p-phenylene analog were also compared with those of the o- and m-phenylene derivatives based on theoretical calculations for further evaluation of the intramolecular electronic interactions.

Anticancer activity of indapamide adsorbed on gold nanoparticles: DFT, in-silico, and in-vitro analysis.

The adsorption properties of the lung cancer agent indapamide (IND) on gold nanoparticles (AuNPs), were studied with the help of surface-enhanced Raman scattering techniques. The structure-activity of the IND and INDA molecule has been studied using DFT/B3LYP methodology. NBO analysis reveals that, both the molecules are stabilized by a C─H… O intramolecular hydrogen bonding, apart from the conjugative and intramolecular charge transfer interactions. The analysis of the electron density of frontier molecular orbital analysis gives a comparative idea of the reactivity, the low kinetic stability, and low value of energy gap indicating the electron transport in the molecule and thereby its bioactivity. The molecular electrostatic potential, local and global reactivity indicators predict the reactive site of the molecules. FT-IR, FT-Raman, and surface-enhanced Raman scattering have been investigated and compared with the theoretical prediction. Effective in-silico (molecular docking) biological activity screening of the molecules was checked on lung cancer cells. In-vitro (surface-enhanced Raman scattering techniques and MTT assay) analysis confirms the results from the in-silico analysis. This study promotes the potential of SERS agents for targeted drug delivery and photothermal therapy and the novelty of the IND and INDA molecule against lung cancer activity.

Multi-sensing response, molecular docking, and anticancer activity of donor–acceptor chalcone containing phenanthrene and thiophene moieties

Donor–Acceptor (D–π–A) chalcone containing phenanthrene and keto-thiophenly moieties, abbreviated as PhTPO, was synthesized and characterized. The solvatochromic effect was investigated in different solvents of various polarities. The absorption and fluorescence spectra have shown bathochromic shifts from non-polar to polar solvents due to intramolecular charge transfer interactions. The fluorescence characteristics (fluorescence intensity, fluorescence maxima, and energy) of PhTPO are highly sensitive to the polarity of the solvents compared to the corresponding absorption spectra. In addition, the inclusion characteristic of PhTPO in different organized assemblies was studied. The spectral changes suggested that PhTPO would be useful to study the microenviromental polarity and evaluation of critical micelle concentrations of the studied surfactants. Reversible acidochromic behavior was observed after addition of H2SO4/NaOH with a significant color change. Further, the optical sensing response towards H+, Co2+, Ni2+, Pb2+ and Cd2+ ions was investigated. Also, it responds well to the tested metal ions as reflected from the changes in both the absorption and emission spectra upon adding different concentrations of the metal salts. The solid complexes of PhTPO with Co2+, Ni2+, Pb2+ and Cd2+ were then synthesized and characterized. Depending on the magnetic moments results, the geometric structures were found to be octahedral and tetrahedral for paramagnetic Co2+, and Ni2+ complexes, respectively, while they are diamagnetic for Pb2+ and Cd2+ complexes. Moreover, the geometry of PhTPO and its complexes were confirmed by the density functional theory (DFT) using DMOL3 program. The binding affinity towards the epidermal growth factor receptor (EGFR) protein was also investigated by the Molecular Operating Environment (MOE) software. The anticancer activity was then evaluated against four different cell lines using MTT assay. The results suggest that the investigated PhTPO would be potential candidate for solvents polarity sensors, as a probe to characterize critical micelle concentrations of surfactants, and sensor for the studied metal ions and H+ proton. In addition, [PhTPONi2+] and [PhTPOCo2+] complexes are good candidate for further antitumor activities studies owing to their potent cytotoxic and anticancer activities compared to the Pb2+ and Cd2+ complexes.