Solid State Research Articles

Application of polyethylene glycol 8000 as plasticizer for the development of ellagic acid and Eudragit® EPO based solid dispersions using hot melt extrusion.

Solid dispersion formation by Hot melt extrusion (HME) is a widely used formulation strategy to improve the solubility and bioavailability of poorly water-soluble drugs. Despite this, they are limited by various factors such as drug-excipient miscibility, poor stability, limited drug loading and extrudability of physical drug-excipient mixtures. In this work, polyethylene glycol 8000 (PEG 8000) was used as a plasticizer for the manufacture of ellagic acid solid dispersions (EASD) with high drug loading. Indeed, EA is a polyphenolic active compound with antimalarial and other promising therapeutic activities. However, its low solubility and low permeability limit its therapeutic use. Solid dispersions formation may overcome this challenge, but its high melting point negatively influences the extrudability of its binary physical mixtures with a high drug loading rate, hence the need to use a plasticizer. Thus, five formulations consisting of EA, Eudragit® EPO and PEG 8000 in the ratio of 15:75:10 (F1), 20:70:10 (F2), 25:65:10 (F3), 15:80:5 (F4) and 20:85:5 (F5) % w/w, respectively, have been extruded, four of which were successful. The extrudates were evaluated by X-ray powder diffraction, FTIR spectroscopy and in vitro dissolution tests. Based on the results of these tests, the F5 formulation was identified as the most promising. Indeed, after 15 min of dissolution test, the dissolution rate of ellagic acid from the formulations was 62.67±3.10%, 58.74±7.23 %, 88.75±3.02% and 83.47±4.40% respectively for formulation F1, F2, F4 and F5. Moreover, the results of the FTIR spectroscopy analyses showed stronger interactions between the different constituents in the F4 and 5 formulations compared to the F1 and 2 formulations. Extruded materials of the F5 formulation, characterized by solid state nuclear magnetic resonance (ssNMR) spectroscopy and subjected to stability studies, showed good physical stability for twelve months under real-time stability study conditions and for six months under accelerated conditions.

Aggregation-induced generation of circularly polarized luminescence in naphthaleneimide-based nanostructures with high dissymmetry factor.

Extensive efforts have been dedicated towards designing new organic materials that display solid-state fluorescence and possess optical activity, thereby leading to the fabrication of materials emitting circularly polarized light. Existing organic materials usually suffer from two limitations, a low dissymmetry factor (glum) and weak or no fluorescence in the solid state. Herein, we have demonstrated a naphthalene imide-based dyad system that remains fluorescent even in powder form and displays circularly polarized luminescence in its aggregated and solid state with significantly high glum values.

Rhodium(I) Complexes with a η1-Fluorenyl-P-phosphanylphosphorane Ligand.

The first example of a P-phosphanylphosphorane, Flu═PCy2-PCy2 (L2; Flu = 9-fluorenyl), has been easily prepared by P-phosphination of lithiated 9-dicyclohexylphosphinofluorene (FluPCy2, L0) with chlorodicyclohexylphosphane. L2 constitutes a new type of P(III)-P(V) organophosphorus compound, a σ3λ3-σ4λ5 species that is stable under an inert atmosphere in the solid state. The reaction of L2 with [Rh(diene)2]BR4 causes metalation of the benzylic carbon (C9) of fluorene, giving κ2-C,P complexes in which fluorene is coordinated in the η1 form. A complex with the weakly coordinating BArF anion has been isolated and fully characterized, including its crystal structure obtained by X-ray diffraction.

High-temperature heat treatment of hydrogen-reduced bauxite residue-calcite pellets for iron particles growth and separationTraitement thermique à haute température de boulettes de résidus de bauxite et calcite réduites à l’hydrogène pour la croissance et la séparation des particules de fer

ABSTRACT Bauxite residue characterised as a polymetallic source containing iron, alumina, titanium, calcium, silicon and rare earth elements offers an opportunity for reduced waste volume and the recovery of valuable metals. This study focuses on the agglomeration of bauxite residue with calcite, followed by hydrogen reduction at 1000°C. The resulting iron particles in the reduced pellets were initially very small distributed in a porous oxide matrix, posing challenges for physical separation methods. To address this issue, further heat treatments were conducted on the reduced pellets in an argon atmosphere, ranging from 1100°C to 1550°C. Phase analysis and microstructural examinations were performed using X-ray powder diffraction and scanning electron microscopy, respectively. Experimental findings indicate that the size of iron particles in the reduced pellets increases with higher heat treatment temperatures. Up to 1200°C, the oxide matrix remains a solid state, transitioning to a semi-molten and molten state above this heat treatment temperature and complete separation of iron from the oxide matrix above 1500°C. An alkali-leachable phase is present in the reduced pellets, initially in the form of calcium aluminate (mayenite), while above 1400°C, this phase dissociates to form monocalcium aluminate, and complete conversion at 1500°C. As observed in the microstructural analysis, there is an increase in the particle size of iron in both the solid and semi-molten states with an increasing in temperature from 1100°C up to 1300°C. This comprehensive study sheds light on the transformative effects of varying heat treatment temperatures on the composition and microstructure of bauxite residue-based materials.

Capturing Mercury-197m/g for Auger Electron Therapy and Cancer Theranostic with Sulfur-Containing Cyclen-Based Macrocycles.

The interest in mercury radioisotopes, 197mHg (t1/2 = 23.8 h) and 197gHg (t1/2 = 64.14 h), has recently been reignited by the dual diagnostic and therapeutic nature of their nuclear decays. These isotopes emit γ-rays suitable for single photon emission computed tomography imaging and Auger electrons which can be exploited for treating small and metastatic tumors. However, the clinical utilization of 197m/gHg radionuclides is obstructed by the lack of chelators capable of securely binding them to tumor-seeking vectors. This work aims to address this challenge by investigating a series of chemically tailored macrocyclic platforms with sulfur-containing side arms, namely, 1,4,7,10-tetrakis[2-(methylsulfanyl)ethyl]-1,4,7,10-tetraazacyclododecane (DO4S), 1,4,7-tris[2-(methylsulfanyl)ethyl]-1,4,7,10-tetraazacyclododecane (DO3S), and 1,7-bis[2-(methylsulfanyl)ethyl]-1,4,7,10-tetraazacyclododecane-4,10-diacetic acid (DO2A2S). 1,4,7,10-Tetrazacyclododecane-1,4,7,10-tetracetic acid (DOTA), the widest explored chelator in nuclear medicine, and the nonfunctionalized backbone 1,4,7,10-tetrazacyclododecane (cyclen) were considered as well to shed light on the role of the sulfanyl arms in the metal coordination. To this purpose, a comprehensive experimental and theoretical study encompassing aqueous coordination chemistry investigations through potentiometry, nuclear magnetic resonance (NMR) spectroscopy, X-ray crystallography, and density functional theory (DFT) calculations, as well as concentration- and temperature-dependent [197m/gHg]Hg2+ radiolabeling and in vitro stability assays in human serum was conducted. The obtained results reveal that the investigated chelators rapidly complex Hg2+ in aqueous media, forming extremely thermodynamically stable 1:1 metal-to-ligand complexes with superior stabilities compared to those of DOTA or cyclen. These complexes exhibited 6- to 8-fold coordination environments, with donors statically bound to the metal center, as evidenced by the presence of 1H-199Hg spin-spin coupling via NMR. A similar octacoordinated environment was also found for DOTA in both solution and solid state, but in this case, multiple slowly exchanging conformers were detected at ambient temperature. The sulfur-rich ligands quantitatively incorporate cyclotron-produced [197m/gHg]Hg2+ under relatively mild reaction conditions (pH = 7 and T = 50 °C), with the resulting radioactive complexes exhibiting decent stability in human serum (up to 75% after 24 h). By developing viable chelators and understanding the impact of structural modifications, our research addresses the scarcity of suitable chelating agents for 197m/gHg, offering promise for its future in vivo application as a theranostic Auger-emitter radiometal.

Molecular origin of the plasticizing effect difference of glycerol with other polyols on plasticizing polyvinyl alcohol (PVA) as elucidated by solid-state NMR

Glycerol has been proved to be an effective plasticizer for polyvinyl alcohol (PVA), which can significantly increase PVA’s processability and ductility, whose molecular origin remains unclear. In current study, the physical structure and chain dynamics of polyol plasticized PVA were studied in detail, including ethylene glycol, glycerol, erythritol, xylitol, and sorbitol under the same addition level. The glycerol plasticized PVA exhibits the most significant reduction in Young’s modulus, enhanced superior toughness, and the lowest melting temperature (195 °C) as compared with other polyols. The molecular mechanism was elucidated through comprehensive analysis, with a particular focus on solid state NMR (SS NMR) results. The physical structure was first elucidated by the Small Angle X-ray Scattering (SAXS) and Wide Angle X-ray Scattering (WAXS). The crystallinity of the glycerol plasticized PVA was the lowest 29 % by WAXS and the thickness of the amorphous layer was the largest 7.76 nm by SAXS among different plasticized PVA films. This suggests the significant influence of glycerol on structure change of PVA. The molecular dynamics information was further accessed by Low Field Nuclear Magnetic Resonance (LF NMR), where two key features are obtained: i) Different dynamics dimensionality. The 1H spin diffusion NMR was used to check the dimensionality from the aspect of chain dynamics. Compared with other plasticizers, LF NMR result shows that glycerol plasticized PVA has a two-dimensional (2D) structure; ii) Chain dynamics heterogeneity in the interphase. With respect to the chain dynamics heterogeneity in the interphase, the glycerol plasticized PVA shows the most heterogeneous dynamics, with the lowest ratio of the rigid amorphous fraction (RAF) of 0.507 in the interphase. Current study provides a versatile analytical strategy to quantify the plasticizing effect.

Iodine(I) pnictogenate complexes as Iodination reagents

Halogen(I) complexes are widely used as halogenation reagents and traditionally feature homoleptic stabilising Lewis bases, though the recent revitalisation of iodine(I) carboxylate chemistry has provided isolable examples of heteroleptic iodine(I) complexes. This work reports iodine(I) pnictogenate complexes stabilised by a Lewis base (L), Ph2P(O)O─I─L, synthesised via cation exchange from the silver(I) precursor, (Ph2P(O)OAg)n. The complexes were characterised in both solution (1H, 1H-15N HMBC, 31P) and the solid state, and supplemented computationally by DFT studies. Interestingly, these iodine(I) pnictogenates demonstrate a range of stabilities, and have been found to excel as iodination reagents in comparison to carbonyl hypoiodites, with comparable reactivity to the eponymous Barluenga’s reagent in the iodination of antipyrine.

A Pillararene-Based Cavitand: Synthesis and Solid-State Capsular Assemblies Induced by Linear Alkanes with Specific Lengths.

Herein, a novel pillararene-based cavitand with fixed planar chirality was synthesized by the SuFEx reaction. As demonstrated by single crystal X-ray analysis, host-guest capsules involving this cavitand and linear alkanes with specific lengths are observed in the solid state. The formation of each capsule is driven by hydrogen bonding interactions between a linear alkane molecule and two cavitand molecules, as well as noncovalent interactions between the two cavitand molecules in this capsule.

Synthesis of Copper–Nickel and Iron–Nickel Alloys by Hydrogen Reduction of Mixtures of Metal Oxide Powders

AbstractThe vast majority of metals production is based on the use of carbon as a reductant and/or a heating fuel. This results in a large amount of carbon dioxide emissions and should be minimized to limit global warming. In this study, powders of copper–nickel alloy and iron–nickel of varying compositions were produced in a single step by reduction of mixtures of Cu2O-NiO and Fe2O3-NiO powders, respectively, using hydrogen as a reductant. Reduction was performed in a horizontal tube furnace at 700 °C for 45 min. All processing was in the solid state and alloys were produced directly from elemental metal oxides. Exhaust gases were analyzed using a gas analyzer to measure the water content to track the progress of the reduction. Reduction was declared complete when the water content in exhaust gases matched the level before hydrogen was introduced. Both copper–nickel and iron–nickel alloys were produced successfully. X-ray diffractometry confirmed the absence of oxides in the product and the presence of solid phases in agreement with the relevant binary phase diagram. Energy-dispersive X-ray spectroscopy in a scanning electron microscope showed macroscopic homogeneity at the expected composition for each powder mixture directly after reduction, with microscopic fluctuations of the order of several mass percent, within the limits of fluctuations observed following typical casting processes. These promising results warrant further investigation to apply this concept to more chemistries and to scale up the process to a pilot scale. Graphical Abstract

Position of substituents directs the electron transfer properties of entatic state complexes: new insights from guanidine-quinoline copper complexes.

In a previous study, we showed that the properties and the ability as an entatic state model of copper guanidine quinoline complexes are significantly influenced by a methyl or methyl ester substituent in the 2-position. To prove the importance of the 2-position of the substituent, two novel guanidine quinoline ligands with a methyl or methyl ester substituent in the 4-position and the corresponding copper complexes were synthesized and characterized in this study. The influence of the substituent position on the copper complexes was investigated with various experimental and theoretical methods. The molecular structures of the copper complexes were examined in the solid state by single-crystal X-ray diffraction (SCXRD) and by density functional theory (DFT) calculations indicating a strong dependency on the substituent position compared to the systems substituted in the 2-position from the previous study. Further, the significantly different influence on the donor properties in dependency on the substituent position was analyzed with natural bond orbital (NBO) calculations. By the determination of the redox potentials, the impact on the electrochemical stabilization was examined. With regard to further previously analyzed guanidine quinoline copper complexes, the electrochemical stabilization was correlated with the charge-transfer energies calculated by NBO analysis and ground state energies, revealing the substituent influence and enabling a comparatively easy and accurate possibility for the theoretical calculation of the relative redox potential. Finally, the electron transfer properties were quantified by determining the electron self-exchange rates via the Marcus theory and by theoretical calculation of the reorganization energies via Nelsen's four-point method. The results gave important insights into the dependency between the ability of the copper complexes as entatic state model and the type and position of the substituent.

Novel Solid‐State Fluorophores, a Series of Cyanostilbene‐Based Amorphous Molecular Materials

AbstractWe have designed and synthesized a novel series of cyanostilbene‐based amorphous molecular materials with different methylene chain lengths, BMAC‐n (n=3,4,5,6), and investigated their emitting properties in solution and various solid states. All BMAC‐n molecules showed solvatochromic fluorescence in solutions. Emission spectra of BMAC‐n molecules in the same solution were identical to one another irrespective of the methylene chain length while the spectra in crystalline states depended on their methylene chain length. As in solutions, emission spectra of their spin‐coated amorphous films were identical to each other irrespective of the methylene chain length. Emission spectra of rubbed amorphous films prepared by grinding their crystals were identical to those for spin‐coated amorphous films; however, comparative studies between spin‐coated and rubbed amorphous films indicated that fluorescence quantum yields and photochemical reactivity depend on the preparation method.

Modeling of the Electronic Properties of M-Doped Supercells (М = Zr, Nb) with a Monoclinic Structure For Lithium-Ion Batteries

The T–x phase diagram of the quasi-binary system Li2O–TiO2 was refined and the isothermal cross section of the ternary Li–Ti–O system at 298 K was constructed. The equilibrium phase regions of Li–Ti–O in the solid state are determined with the participation of boundary binary oxides and four intermediate ternary compounds , , and . Using the density functional theory (DFT LSDA) method, the formation energies of the indicated ternary compounds of the Li2O–TiO2 system were calculated and the dependence of on the composition was plotted. Ab initio modeling of supercells based on M-doped anode material based on the (LTO) compound with a monoclinic structure () was carried out. It has been shown that partial substitution of cations and oxygen in the m-LTO–M structure increases the efficiency of a lithium-ion battery (LIB) both by stabilizing the structure and by increasing the diffusion rate of . Due to the contribution of d-orbitals (Zr4+-4d, Nb3+-4d orbitals) to the exchange energy, partial polarization of electronic states occurs and the electronic conductivity of m-LTO–M increases. The formation of oxygen vacancies in the m-LTO–M crystal lattice, as in binary oxides, can create donor levels and improve the transport of and electrons. M-doping of the m-LTO structure by replacing cations, in particular lithium, with Zr or Nb atoms noticeably reduces the band gap (Eg) of m-LTO–M supercells. In this case, in the m-LTO–M band structure, the Fermi level shifts to the conduction band and the band gap narrows. Decreasing the Eg value increases the electronic and lithium-ion conductivity of m-LTO–M supercells.

Integration of High‐Tc Superconductors with High‐Q‐Factor Oxide Mechanical Resonators

AbstractMicro‐mechanical resonators are building blocks of a variety of applications in basic science and consumer electronics. This device technology is mainly based on well‐established and reproducible silicon‐based fabrication processes with outstanding performances in term of mechanical Q‐factor and sensitivity to external perturbations. Broadening the functionalities of micro‐electro‐mechanical systems (MEMS) by the integration of functional materials is a key step for both applied and fundamental science. However, combining functional materials with silicon‐based devices is challenging. An alternative approach is directly fabricating MEMS based on compounds inherently showing non‐trivial functional properties, such as transition metal oxides. Here, a full‐oxide approach is reported, where a high‐ superconductor YBa2Cu3O7 (YBCO) is integrated with high Q‐factor micro‐bridge resonators made of single‐crystal LaAlO3 (LAO) thin films. LAO resonators are tensile strained, with a stress of about 350 MPa, show a Q‐factor above 200k, and have low roughness. YBCO overlayers are grown ex situ by pulsed laser deposition and YBCO/LAO bridges show zero resistance below 78 K and mechanical properties similar to those of bare LAO resonators. These results open new possibilities toward the development of advanced transducers, such as bolometers or magnetic field detectors, as well as experiments in solid state physics, material science, and quantum opto‐mechanics.

Fluorescence Enhancement of Single V2 Centers in a 4H-SiC Cavity Antenna.

Solid state quantum emitters are a prime candidate in distributed quantum technologies since they inherently provide a spin-photon interface. An ongoing challenge in the field, however, is the low photon extraction due to the high refractive index of typical host materials. This challenge can be overcome using photonic structures. Here, we report the integration of V2 centers in a cavity-based optical antenna. The structure consists of a silver-coated, 135 nm-thin 4H-SiC membrane functioning as a planar cavity with a broadband resonance yielding a theoretical photon collection enhancement factor of ∼34. The planar geometry allows us to identify over 20 single V2 centers at room temperature with a mean (maximum) count rate enhancement factor of 9 (15). Moreover, we observe 10 V2 centers with a mean absorption line width below 80 MHz at cryogenic temperatures. These results demonstrate a photon collection enhancement that is robust to the lateral emitter position.

Can pulsed laser treatment reduce microbial adhesion on the surface of resin denture base materials?

Abstract Objectives: The present work investigates the influence of pulsed nanosecond laser patterning of two commercial heat cure poly (methyl methacrylate) denture base materials, Trevalon and DPI heat cure, on their surface characteristics such as roughness, hydrophobicity, and microbial adhesion. 
Methods: A Q-switched Nd-YAG solid state nanosecond pulsed laser at a wavelength of 532 nm with a fluence of 2.55x1010 W/cm2 having a pulse frequency of 10 Hz was used at varying translation stage speed and vertical spacing for the surface patterning of denture base materials. The surface properties of control and patterned materials were characterized by measuring the compositional changes, wettability, and roughness. Microbial adhesion was assessed by incubating the specimens in Candida albicans suspension at 37°C for 2 hours followed by estimating the number of adherent Candida cells. 
Results: The micro-Raman spectroscopic studies indicated no chemical changes in the materials due to laser patterning. However, laser patterning increased the average surface roughness from 0.02 ± 0.005 and 0.04 ± 0.003 µm to 3.85 ± 0.20 µm and 3.70 ± 0.12 µm respectively for Trevalon and DPI heat cure materials. In addition, a reduction in the surface wettability was evident as manifested by an increase in water contact angle from 76 ± 2° to 105 ± 1° for Trevalon and from 72 ± 1° to 97 ± 1° for DPI heat cure. Finally, the microbial adhesion studies clearly indicated that the surfaces with higher hydrophobicity and roughness following laser patterning exhibited reduced microbial adhesion. 
Significance: Laser patterning can be utilized to tune the surface features of denture base materials and thus offer a promising method to create microbial adhesion resistant surfaces. Clinically, such surfaces help in reducing the incidence of denture stomatitis, especially in immunocompromised patients, without altering the composition and bulk properties of denture base materials.

Assessment of indoor radon concentration in the dwellings of the industrial areas of Kannur District, Kerala.

All organisms on the earth-crest are exposed to natural background radiation since the evolution of the earth, as many environmental matrices such as soil, air, water bodies, vegetation, etc., act as the sources of natural radioactivity. The present study deals with the evaluation of indoor concentration of 222Rn (radon) in different dwellings with various construction materials used for the roof and floor in the industrial sites of Kannur district, Kerala. A pinhole-based dosemeter coupled with LR-115 Solid State Nuclear Track Detector and Direct Radon Progeny Sensor (DRPS) were respectively used for the measurement of indoor radon concentration and equilibrium equivalent concentration of radon. The indoor radon concentrations were found to vary from 102.30 Bqm-3 to 184.75 Bqm-3 and the values were within the recommended limits provided by International Commission on Radiological Protection (ICRP). The annual effective doses and excess lifetime cancer risks were observed in the range of 2.58-4.66 mSvy-1 and 7.68×10-3-15.60×10-3, respectively, and both exceed the world average values recommended by United Nations Scientific Committee on the Effects of Atomic Radiation (UNSCEAR) 2000. The study shows that, the houses with marble floors and concrete roofs have comparatively higher values of radon concentration, which indicates the significant contribution of construction materials to the enhanced radiation levels inside the dwellings.

Taming 2,2'-biimidazole ligands in trivalent chromium complexes.

Complete or partial replacement of well-known five-membered chelating 2,2'-bipyridine (bipy) or 1,10-phenanthroline (phen) ligands with analogous didentate 2,2'-biimidazole (H2biim) provides novel perspectives for exploiting the latter pH-tuneable bridging unit for connecting inert trivalent chromium with cationic partners. The most simple homoleptic complex [Cr(H2biim)3]3+ and its stepwise deprotonated analogues are only poorly soluble in most solvents and their characterization is limited to some solid-state structures, in which the pseudo-octahedral [CrN6] units are found to be intermolecularly connected via peripheral N-H⋯X hydrogen bonds. Moreover, the associated high-energy stretching N-H vibrations drastically quench the targeted near infrared (NIR) CrIII-based phosphorescence, which makes these homoleptic building blocks incompatible with the design of molecular-based luminescent assemblies. Restricting the number of bound 2,2'-biimidazole ligands to a single unit in the challenging heteroleptic [Cr(phen)2(Hxbiim)](1+x)+ (x = 2-0) complexes overcomes the latter limitations and allows (i) the synthesis and characterization of these [CrN6] chromophores in the solid state and in solution, (ii) the stepwise and controlled deprotonation of the bound 2,2'-biimidazole ligand and (iii) the implementation of Cr-centered phosphorescence with energies, lifetimes and quantum yields adapted for using the latter chromophores as sensitizers in promising 'complex-as-ligand' strategies.

Hypervalent Iodine (III)-Based Complexation for Chiroptical Supramolecular Glass, Deep Eutectic Solvent and Luminescent Switch.

Hypervalent iodine(III) have widely been utilized for organic synthetic reagents. They are also recognized as positive charge-assisted, exceptionally robust biaxial halogen bond donors, while their potential in supramolecular materials is barely explored. This work reports a cyclic diaryliodonium ion as biaxial halogen bonding donor that displays remarkable binding affinity toward phenanthroline or acridine acceptors with chiral pendants. Biaxial halogen bonding enables chiroptical evolution in solution, allowing for rational control over supramolecular chirality. Leveraging their strong binding affinity, the halogen bonding complexes manifested amorphous properties and deep eutectic behavior in the solid state. Capitalizing on these attributes, this work achieves the successful preparation of supramolecular glasses and deep eutectic solvents. Additionally, halogen bonding appended light irradiation-triggered luminescence through a hydrogen atom transfer process, showing applications in anti-counterfeit and display.

Mechanochemical synthesis of iron aluminyl complexes.

A series of iron aluminyl complexes have been synthesised in good crystalline yields from reactions between bulky diamido aluminium iodide complexes and K[Fe(CO)2Cp] in the solid state. The series of metal-metal bonded complexes have been characterised by X-ray crystallography and were investigated using density functional theory to probe the effects of ligand substitution on the Al-Fe bond.

Pentafluorophenyl Copper–Biarylsulfoxide Complexes: Synthesis and Photoreactivity

Pentafluorophenyl copper(I)–biarylsulfoxide complexes, existing as [Cu(C6F5)]4L2, both in solution and in the solid state, were prepared and thoroughly characterized. Subsequently, the photochemistry of the complexes was explored, showing inherent photoreactivity of the biarylsulfoxide moiety within the coordination sphere of the copper. Photoinduced cross-coupling reactions between the anthryl moiety of bis-anthracenylsulfoxide and pentafluorobenzene, and synthesis of Cu2O (cuprite), were demonstrated.