Development of Composite Semiconductor Films Based on Organotin Complexes Doped with Cobalt Porphine for Applications in Organic Diodes.

In this work, we present the green synthesis of complex - derived from β-hidroxymethylidene indanones by ultrasound, which allowed for the obtaining of compounds in a shorter time and with good yields. These organotin complexes were then doped with cobalt porphine and incorporated into a poly(3,4-ethylenedioxythiophene):poly(4-styrenesulfonate) matrix to manufacture composite semiconductor films. The semiconductor films were characterized through atomic force microscopy, examining their topography, Knoop hardness (around 17 HK), and tensile strength, which varied from 5 × 10 to 7 × 10 Pa.

Innovative Application of Salophen Derivatives in Organic Electronics as a Composite Film with a Poly(3,4-Ethylenedioxythiophene)-poly(styrenesulfonate) Matrix.

In this work, we present the innovative synthesis of salophen (acetaminosalol) derivatives in a solvent-free environment by high-speed ball milling, using a non-conventional activation method, which allowed obtaining compounds in a shorter time and with a better yield. Furthermore, for the first time, the salophen derivatives were deposited as composite films, using a matrix of poly 3,4-ethylene dioxythiophene:polystyrene sulfonate (PEDOT:PSS) polymer. Significant findings include the transformation from the benzoid to the quinoid form of PEDOT post-IPA treatment, as evidenced by Raman spectroscopy.

Synthesis of New Ruthenium Complexes and Their Exploratory Study as Polymer Hybrid Composites in Organic Electronics.

Polymeric hybrid films, for their application in organic electronics, were produced from new ruthenium indanones in poly(methyl methacrylate) (PMMA) by the drop-casting procedure. Initially, the synthesis and structural characterization of the ruthenium complexes were performed, and subsequently, their properties as a potential semiconductor material were explored. Hence hybrid films in ruthenium complexes were deposited using PMMA as a polymeric matrix.

Synthesis of Functionalized Tetrasubstituted Allenes by the Addition of Bis(trimethylsilyl)ketene Acetals to Ynones Catalyzed by Gold(I).

We have developed a straightforward and rapid methodology for the synthesis of tetrasubstituted allenes bearing carboxylic acids in the 1,3-position through the gold(I)-catalyzed nucleophilic addition of bis(trimethylsilyl)ketene acetals to ynones. The reaction was evaluated with several substrates, and 21 allenes were obtained in moderate to good yields. Using DFT calculations, we studied the mechanism of the reaction, which suggested a nucleophilic 1,4-addition pathway.

Structural determination, characterization and computational studies of doped semiconductors base silicon phthalocyanine dihydroxide and dienynoic acids.

The chemical doping of silicon phthalocyanine dihydroxide (SiPc(OH)), with (2E, 4Z)-5, 7-diphenylhepta-2, 4-dien-6-ynoic acids (DAc) with electron-withdrawing (BrDAc) and electron-donating (MeODAc) substituents is the main purpose of this work. Theoretical calculations were carried out on Gaussian16 software, with geometrical optimization of all involved species, and obtention of the highest occupied molecule orbital HOMO), lowest unoccupied molecular orbital (LUMO), and the respective energy gaps. The theoretical calculations show two hydrogen bridge formations: the first one as a peripheral interaction between the terminal oxygen atoms from the acid unit and hydrogen atoms from the phthalocyanine aromatic rings.

Design of Promising Uranyl(VI) Complexes Thin Films with Potential Applications in Molecular Electronics.

In this work, it is proposed the development of organic semiconductors (OS) based on uranyl(VI) complexes. The above by means of the synthesis and the characterization of the complexes by Infrared spectroscopy, Nuclear magnetic resonance spectroscopy, mass spectrometry, and X-ray diffraction. Films of these complexes were deposited and subsequently, topographic and structural characterization was carried out by Scanning Electron Microscopy, X-ray diffraction, and Atomic Force Microscopy.

Synthesis, Cytotoxic Activity and In Silico Study of Novel Dihydropyridine Carboxylic Acids Derivatives.

To aid the possible prevention of multidrug resistance in tumors and cause lower toxicity, a set of sixteen novel dihydropyridine carboxylic acids derivatives were produced; thus, the activation of various ynones with triflic anhydride was performed, involving a nucleophilic addition of several (trimethylsilyl) ketene acetals, achieving good yields requiring easy workup. The target molecules were unequivocally characterized by common spectroscopic methods. In addition, two of the tested compounds (, and ) were selected to perform in silico studies due to the highest cytotoxic activity towards the HCT-15 cell line (7.

Fabrication and Characterization of Hybrid Hole Transporting Layers of Organotin (IV) Semiconductors within Molybdenum Oxide/Poly(3,4-ethylenedyoxithiophene) Polystyrene Sulfonate Matrices.

The hybrid film of molybdenum oxide (MoO) and poly(3,4-ethylenedyoxithiophene) polystyrene sulfonate (PEDOT:PSS) is a promising candidate for use as hole transport layer (HTL) in low-cost devices. A fast, controllable and economic process was used to fabricate high-performance HTLs by adding organotin (IV) semiconductors to the MoO/PEDOT:PSS films. These hybrid films were fabricated by spin-coating and the MoO/PEDOT:PSS-organotin (IV) complex films were characterized by infrared spectroscopy, scanning electron microscopy (SEM) and atomic force microscopy (AFM).

Innovative Incorporation of Poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate) as Hole Carrier Transport Layer and as Anode for Organic Solar Cells Performance Improvement.

In this work, we present a comparative study of benzoid poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate) (PEDOT:PSS) as electrode and as hole carrier transport layer (HTL) in the manufacture of organic photovoltaic devices using Fischer metal-carbene complexes. The performance of the different devices was evaluated for solar cell applications. Scanning electronic microscopy (SEM) and X-ray diffraction (XRD) were used to characterize the thin films that integrated the devices.

Multifunctional Fischer Aminocarbene Complexes as Hole or Electron Transporting Layers in Organic Solar Cells.

A new series of Fischer carbenes have been synthetized and examined as hole-transporting or electron-transporting layers (HTLs or ETLs) in the fabrication of organic solar cells (OSCs). The synthesis of three Fischer aminocarbene complexes with the general formula [Cr(CO)₅{C(NHCH₂)Ar}] (Ar = 2-pyridyl (), 3-pyridyl () and 4-pyridyl ()) is reported. The molecular structure of complex has been confirmed by X-ray analysis.

Synthesis, Molecular Docking, and Antimycotic Evaluation of Some 3-Acyl Imidazo[1,2-a]pyrimidines.

A series of 3-benzoyl imidazo[1,2-]pyrimidines, obtained from -heteroarylformamidines in good yields, was tested in silico and in vitro for binding and inhibition of seven species ( (ATCC 10231), (CD36), (CBS138), (ATCC 6260), , (ATCC 6358) and (MYA-3404)). To predict binding mode and energy, each compound was docked in the active site of the lanosterol 14α-demethylase enzyme (CYP51), essential for fungal growth of species. Antimycotic activity was evaluated as the 50% minimum inhibitory concentration (MIC50) for the test compounds and two reference drugs, ketoconazole and fluconazole.

Phosphine/Sulfoxide-Supported Carbon(0) Complex.

A new carbon(0) complex 2 with two different L ligands, a phosphine and a sulfoxide, was synthesized and fully characterized. This new type of carbone exhibits excellent coordination ability, in contrast to the related phosphine/sulfide-supported carbon(0) complexes. Several organometallic complexes were isolated and, of special interest, the ν (CO) value of Rh -dicarbonyl complex indicates that 2 has a donor capability superior to classical NHCs.

New Development of Membrane Base Optoelectronic Devices.

It is known that one factor that affects the operation of optoelectronic devices is the effective protection of the semiconductor materials against environmental conditions. The permeation of atmospheric oxygen and water molecules into the device structure induces degradation of the electrodes and the semiconductor. As a result, in this communication we report the fabrication of semiconductor membranes consisting of Magnesium Phthalocyanine-allene (MgPc-allene) particles dispersed in Nylon 11 films.

Stereodivergent Mannich reaction of bis(trimethylsilyl)ketene acetals with N-tert-butanesulfinyl imines by Lewis acid or Lewis base activation, a one-pot protocol to obtain chiral β-amino acids.

We report a one-pot synthesis of chiral β-amino acids by the Mannich addition of bistrimethylsilyl ketene acetals to N-tert-butanesulfinyl imines followed by the removal of the chiral auxiliary. The synthesis and isolation of pure β-amino acid hydrochlorides were conducted under mild conditions, without strong bases and this method is operationally simple. The stereoselective reaction was promoted by two different activation methods that lead to different stereoisomers: (1) Lewis Acid (LA) catalysis with boron trifluoride diethyl etherate and (2) Lewis Base (LB) catalysis with tetrabutylammonium difluorotriphenylsilicate.

An Efficient Strategy for the Synthesis of 1-(Trifluoromethylsulfonamido)propan-2-yl Esters and the Evaluation of Their Cytotoxic Activity.

An efficient method for the synthesis of 1-(trifluoromethylsulfonamido)propan-2-yl benzoates is described, the products of the reaction were characterized by heteronuclear single quantum coherence spectroscopy (HSQC), heteronuclear multiple bond correlation (HMBC) and NMR experiments. The overall process began with the activation of the oxazoline ring by triflic anhydride, followed by the opening of the five-membered ring in the 5-methyl-2-phenyl-4,5-dihydrooxazole system. The cytotoxic activity of the new trifluoromethyl sulfonamides was evaluated with six cancer cell lines and human gingival fibroblasts, posteriorly analyzing the influence on cytotoxicity exerted by the withdrawing and donor substituents at the para-position of the phenyl ring.

Nanostructured Thin Films Obtained from Fischer Aminocarbene Complexes.

The synthesis of four amphiphilic organometallic complexes with the general formula RC = M(CO)₅NH(CH₂)CH₃, where R is a ferrocenyl 2(a-b) or a phenyl 4(a-b) group as a donor moiety and a Fischer carbene of chromium (0) or tungsten (0) as an acceptor group, are reported. These four push-pull systems formed Langmuir (L) monolayers at the air-water interface, which were characterized by isotherms of surface pressure molecular area and compression/expansion cycles (hysteresis curves); Brewster angle microscopic images were also obtained. By using the Langmuir-Blodgett (LB) method, molecular monolayers were transferred onto glass substrates forming Z-type multilayers.

Green approach—multicomponent production of boron—containing hantzsch and biginelli esters.

Multicomponent reactions are excellent methods that meet the requirements of green chemistry, by reducing the number of steps, and consequently reducing purification requirements. Accordingly, in this work, 11 novel hybrid-boron-containing molecules, namely eight 1,4-dihydropyridines and three 3,4-dihydropyrimidinones, derived from formylphenylboronic acids (ortho, meta and para), were obtained using a green approach, involving H-4CR and B-3CR practices, in the presence of ethanol, which is a green solvent, and using three comparatively different modes of activation (mantle heating, yield 3%-7% in 24 h, Infrared Radiation (IR) irradiation, yield 12%-17% in 12 h, and microwave irradiation, yield 18%-80%, requiring very low reaction times of 0.25-0.

Synthesis of Fischer type-carbene complexes containing a coordinated thioimidate structural motif.

This paper describes a tandem strategy to synthesize a series of new Fischer carbene complexes [(CO)(4)M=C[N-(CH(2))(4)-]CH=C(NRR')(SR'); M = Cr, W; R = Ar, R' = Me, -(CH(2))(2)-] with a thioimide or thiazoline fragment, in which the sulfur or nitrogen atom is coordinated to a metal center, depending on the nature of alkylating groups included as R'. We have trapped by protonation the proposed intermediate as the thioamide 12 [(CO)(5)W=[N-(CH(2))(4)-]CH(2)C(S)NHPh], which reveals the pathway of this reaction.

Electrical and optical properties of copper and nickel molecular materials with tetrabenzo [b,f,j,n] [1,5,9,13] tetraazacyclohexadecine thin films grown by the vacuum thermal evaporation technique.

Semiconducting molecular-material thin-films of tetrabenzo (b,f,j,n) [1,5,9,13] tetraazacyclohexadecine copper(II) and nickel(II) bisanthraflavates have been prepared by using vacuum thermal evaporation on Corning glass substrates and crystalline silicon wafers. The films thus obtained were characterized by infrared spectroscopy (FTIR), atomic force microscopy (AFM), ultraviolet-visible (UV-vis) spectroscopy and ellipsometry. IR spectroscopy showed that the molecular-material thin-films exhibit the same intra-molecular bonds as the original compounds, which suggests that the thermal evaporation process does not significantly alter their bonds.

Electrical and optical properties of C46H22N8O4KM (M=Co, Fe, Pb) molecular-material thin films prepared by the vacuum thermal evaporation technique.

In this work, the synthesis of new materials formed from metallic phthalocyanines (Pcs) and double potassium salt from 1,8-dihydroxianthraquinone is reported. The newly synthesized materials were characterized by scanning electron microscope (SEM), atomic force microscopy (AFM), infrared (IR) and Ultraviolet-visible (UV-vis) spectroscopy. The powder and thin-film samples of the synthesized materials, deposited by vacuum thermal evaporation, show the same intra-molecular bonds as in the IR spectroscopy studies, which suggests that the thermal evaporation process does not alter these bonds.

Synthesis and characterization of novel dinuclear copper(I) complexes. Dimerization of [CuL(PPh3)2] (L = methyl 3-hydroxy-3-(p-R-phenyl)-2-propenedithioate).

We report the synthesis of new copper(I) complexes 6a-e from methyl 3-hydroxy-3-(p-R-phenyl)-2-propenedithioate ligands. These complexes were characterized by IR and 1H, 13C, and 31P NMR spectroscopy. The expected O,S-coordination mode was confirmed by the X-ray diffraction studies of 6b and 6e.

Synthesis, characterization, and tautomerism of four novel copper(I) complexes from 3-hydroxy-3-(p-R-phenyl)-2-propenedithioic acids.

The paper describes the synthesis and structural characterization of four novel copper(I) complexes [CuL(PPh(3))(2)] (L = 3-hydroxy-3-(p-R-phenyl)-2-propenedithioate). In addition, a tautomeric equilibrium in solution was found and Hammett correlations with (13)C NMR parameters were studied. The structure of one complex was fully established by X-ray diffraction analysis.

New pinch-porphyrin complexes with quantum mixed spin ground state S=3/2,5/2 of iron (III) and their catalytic activity as peroxidase.

New complexes of the pinch-porphyrin family were obtained from the dimethylester of (proto-, meso-, and deutero-porphyrinato)iron(III) with the ligand [N,N'-bis-pyridin-2-ylmethyl-propane-1,3-diamine] 1-3 and with the ligand [N-pyridin-2-ylmethyl-N'-[3-[(pyridin-2-ylmethyl)-amino]-propyl]-propane-1,3-diamine] 4-6. The UV/VIS studies of 1-6 indicate an increase in the distortion of the ligand field excited state. The 1H NMR spectra of 1-6 at RT and over the range 223-328 K show iron(III)-complexes with quantum mixed spin state (qms) S=5/2, S=3/2.