Journal articles: 'Fully fluorinated organic sensitizers'

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Jia, Xiaowei, Weiyi Zhang, Xuefeng Lu, Zhong-Sheng Wang, and Gang Zhou. "Efficient quasi-solid-state dye-sensitized solar cells based on organic sensitizers containing fluorinated quinoxaline moiety." J. Mater. Chem. A 2, no. 45 (2014): 19515–25. http://dx.doi.org/10.1039/c4ta04884a.

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Kitamura, Takayuki, Yuji Wada, and Shozo Yanagida. "Fluorinated aromatics as sensitizers for photo-splitting of water." Journal of Fluorine Chemistry 105, no. 2 (September 2000): 305–11. http://dx.doi.org/10.1016/s0022-1139(00)00209-8.

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Mohd Nizar, Siti Nabilla Aliya, Siti Noor Farhana Ab Rahman, Muhamad Fikri Zaini, Ainizatul Husna Anizaim, Ibrahim Abdul Razak, and Suhana Arshad. "The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents." Crystals 11, no. 11 (November 8, 2021): 1357. http://dx.doi.org/10.3390/cryst11111357.

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Two newly halogenated chalcones, derivatives of C15H10ClFO (CH-ClF) and C15H10F2O (CH-FF), were synthesized using the Claisen–Schmidt condensation method. Both compounds were crystallized using a slow evaporation method, forming a monoclinic crystal system with a space group of P21 and P21/c, respectively. The compounds were further analyzed using spectroscopic techniques such as Fourier Transform Infrared (FTIR), Nuclear Magnetic Resonance (NMR), and Ultraviolet–Visible (UV–vis) analyses. The single crystal X-ray diffraction method revealed the existence of C−H⋯O and C−H⋯F intermolecular interactions in CH-FF. Hirshfeld surface analysis was performed to confirm the existence of intermolecular interactions in the compounds. The molecular geometries obtained from the X-ray structure determination were further used to optimize the structures using density functional theory (DFT), with the B3LYP/6-311G++(d,p) basis set in the ground state. The TD-DFT/B3LYP method was used to obtain the electronic properties and the HOMO–LUMO energy gap. Both compounds exhibited A-π-A architecture with different halogen substituents in which the CH-FF, containing -fluoro substituents, possessed good electron injection ability due to its electronegative properties. This increased the flow of the charge transfer for the dye regeneration process and enhanced the efficiency of the dye-sensitized solar cell (DSSC).

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Zehra, Syeda Tazeen, Shouang Lan, Hao Zhang, Jinggong Liu, Shuang Yang, and Xinqiang Fang. "Access to enantioenriched molecules with diverse fluorinated tetrasubstituted stereocenters using hydroxy as a kinetic resolution auxiliary group." Organic Chemistry Frontiers 9, no. 4 (2022): 1040–47. http://dx.doi.org/10.1039/d1qo01493e.

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We describe in this paper that using secondary OH as the kinetic resolution auxiliary group, a series of previously unavailable fluorinated fully-substituted carbon molecules can be obtained with excellent level of enantioselectivities.

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Wityk, Paweł, Dorota Kostrzewa-Nowak, Beata Krawczyk, Michał Michalik, and Robert Nowak. "X-ray and UV Radiation Damage of dsDNA/Protein Complexes." Molecules 26, no. 11 (May 24, 2021): 3132. http://dx.doi.org/10.3390/molecules26113132.

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Radiation and photodynamic therapies are used for cancer treatment by targeting DNA. However, efficiency is limited due to physico-chemical processes and the insensitivity of native nucleobases to damage. Thus, incorporation of radio- and photosensitizers into these therapies should increase both efficacy and the yield of DNA damage. To date, studies of sensitization processes have been performed on simple model systems, e.g., buffered solutions of dsDNA or sensitizers alone. To fully understand the sensitization processes and to be able to develop new efficient sensitizers in the future, well established model systems are necessary. In the cell environment, DNA tightly interacts with proteins and incorporating this interaction is necessary to fully understand the DNA sensitization process. In this work, we used dsDNA/protein complexes labeled with photo- and radiosensitizers and investigated degradation pathways using LC-MS and HPLC after X-ray or UV radiation.

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Lum, Kah Yean, Jonathan M. White, Daniel J. G. Johnson, Vicky M. Avery, and Rohan A. Davis. "Synthesis and characterisation of new antimalarial fluorinated triazolopyrazine compounds." Beilstein Journal of Organic Chemistry 19 (January 31, 2023): 107–14. http://dx.doi.org/10.3762/bjoc.19.11.

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Nine new fluorinated analogues were synthesised by late-stage functionalisation using Diversinate™ chemistry on the Open Source Malaria (OSM) triazolopyrazine scaffold (Series 4). The structures of all analogues were fully characterised by NMR, UV and MS data analysis; three triazolopyrazines were confirmed by X-ray crystal structure analysis. The inhibitory activity of all compounds against the growth of the malaria parasite Plasmodium falciparum (3D7 and Dd2 strains) and the cytotoxicity against a human embryonic kidney (HEK293) cell line were tested. Some of the compounds demonstrated moderate antimalarial activity with IC50 values ranging from 0.2 to >80 µM; none of the compounds displayed any cytotoxicity against HEK293 cells at 80 µM. Antimalarial activity was significantly reduced when C-8 of the triazolopyrazine scaffold was substituted with CF3 and CF2H moieties, whereas incorporation of a CF2Me group at the same position completely abolished antiplasmodial effects.

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Cheplakova, Anastasia M., Denis G. Samsonenko, and Vladimir P. Fedin. "Octafluorobiphenyl-4,4′-dicarboxylate as a ligand for metal-organic frameworks: progress and perspectives." Pure and Applied Chemistry 92, no. 7 (July 28, 2020): 1081–92. http://dx.doi.org/10.1515/pac-2019-1210.

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AbstractWhile metal-organic frameworks based on aromatic carboxylates are very numerous and well investigated, the chemistry of their fully fluorinated analogues is at the very beginning. This minireview aims at summarizing all metal complexes with octafluorobiphenyl-4,4′-dicarboxylate (oFBPDC2−) anion and in particular, porous coordination polymers, their syntheses, crystal structures and functional properties highlighting the importance of further investigation of such systems.

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Utecht-Jarzyńska, Greta, Anna Kowalczyk, and Marcin Jasiński. "Fluorinated and Non-Fluorinated 1,4-Diarylpyrazoles via MnO2-Mediated Mechanochemical Deacylative Oxidation of 5-Acylpyrazolines." Molecules 27, no. 23 (December 2, 2022): 8446. http://dx.doi.org/10.3390/molecules27238446.

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A solvent-free two-step synthesis of polyfunctionalized pyrazoles under ball-milling mechanochemical conditions was developed. The protocol comprises (3 + 2)-cycloaddition of in situ generated nitrile imines and chalcones, followed by oxidation of the initially formed 5-acylpyrazolines with activated MnO2. The second step proceeds via an exclusive deacylative pathway, to give a series of 1,4-diarylpyrazoles functionalized with a fluorinated (CF3) or non-fluorinated (Ph, COOEt, Ac) substituent at C(3) of the heterocyclic ring. In contrast, MnO2-mediated oxidation of a model isomeric 4-acylpyrazoline proceeded with low chemoselectivity, leading to fully substituted pyrazole as a major product formed via dehydrogenative aromatization. The presented approach extends the scope of the known methods carried out in organic solvents and enables the preparation of polyfunctionalized pyrazoles, which are of general interest in medicine and material sciences.

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Şologan, Maria, Cristina Cantarutti, Silvia Bidoggia, Stefano Polizzi, Paolo Pengo, and Lucia Pasquato. "Routes to the preparation of mixed monolayers of fluorinated and hydrogenated alkanethiolates grafted on the surface of gold nanoparticles." Faraday Discussions 191 (2016): 527–43. http://dx.doi.org/10.1039/c6fd00016a.

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The use of binary blends of hydrogenated and fluorinated alkanethiolates represents an interesting approach to the construction of anisotropic hybrid organic–inorganic nanoparticles since the fluorinated and hydrogenated components are expected to self-sort on the nanoparticle surface because of their reciprocal phobicity. These mixed monolayers are therefore strongly non-ideal binary systems. The synthetic routes we explored to achieve mixed monolayer gold nanoparticles displaying hydrogenated and fluorinated ligands clearly show that the final monolayer composition is a non-linear function of the initial reaction mixture. Our data suggest that, under certain geometrical constraints, nucleation and growth of fluorinated domains could be the initial event in the formation of these mixed monolayers. The onset of domain formation depends on the structure of the fluorinated and hydrogenated species. The solubility of the mixed monolayer nanoparticles displayed a marked discontinuity as a function of the monolayer composition. When the fluorinated component content is small, the nanoparticle systems are fully soluble in chloroform, at intermediate content the nanoparticles become soluble in hexane and eventually they become soluble in fluorinated solvents only. The ranges of monolayer compositions in which the solubility transitions are observed depend on the nature of the thiols composing the monolayer.

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Bruma, M., I. Sava, F. Mercer, I. Negulescu, W. Daly, J. Fitch, and P. Cassidy. "Synthesis and properties of fluorinated poly(ester-imide)s." High Performance Polymers 7, no. 4 (August 1995): 411–20. http://dx.doi.org/10.1088/0954-0083/7/4/003.

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A series of new, fluorinated poly(ester-imides)s has been synthesized by solution condensation, in a high-boiling-point solvent, of dihydroxy compounds containing imide and hexafluoroisopropylidene units with diacid chlorides containing preformed ester groups. Solutions of these polymers in NMP or in a mixture of trifluoroacetic acid with chloroform were cast into colourless, thin, flexible films having a low dielectric constant. These polymers show high thermal stability, with the initial decomposition temperature being over 400cC. The glass transition temperature is in the range 215-272C for fully aromatic structures and is about 170 TC for those polymers containing some ethylene groups along with aromatic ones. All these characteristics are discussed and compared with those of related poly(esterimide)s which do not contain 6F groups.

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Pugliese, D., N. Shahzad, A. Sacco, G. Musso, A. Lamberti, G. Caputo, E. Tresso, S. Bianco, and C. F. Pirri. "Fast TiO2Sensitization Using the Semisquaric Acid as Anchoring Group." International Journal of Photoenergy 2013 (2013): 1–8. http://dx.doi.org/10.1155/2013/871526.

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Metal-free dye molecules for dye-sensitized solar cells application can avoid some of the typical drawbacks of common metal-based sensitizers, that are high production costs, relatively low molar extinction coefficient in the visible region, limited availability of precursors, and waste disposal issues. Recently we have proposed an innovative organic dye based on a simple hemi-squaraine molecule (CT1). In the present work, the effect of the sensitization time of the TiO2photoelectrode in the dye solution is studied with the aim of optimizing the performance of CT1-based DSCs. Moreover, the addition of the chenodeoxycholic acid (CDCA) as coadsorbent in the dye solution at different concentrations is investigated. Both CT1-sensitized mesoporous TiO2photoanodes and complete solar cells have been fully characterized in their electrical and absorption properties. We have found that the best photoconversion performances are obtained with 1 hour of impregnation time and a 1 mM CDCA concentration. The very fast kinetics in dye adsorption, with optimal sensitization steps almost 15 times faster than conventional Ru-based sensitizers, confirms the theoretical predictions and indicates a strong interaction of the semisquaric acid group with the anatase surface. This result suggests that this small molecule can be a promising sensitizer even in a continuous industrial process.

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Huang, Jian Qiang, Zackaria Nairoukh, and Ilan Marek. "Electrophilic fluorination of stereodefined disubstituted silyl ketene hemiaminals en route to tertiary α-fluorinated carbonyl derivatives." Organic & Biomolecular Chemistry 16, no. 7 (2018): 1079–82. http://dx.doi.org/10.1039/c8ob00067k.

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A highly diastereoselective synthesis of tertiary α-fluoro carbonyl compounds is reported in only two chemical steps from a simple alkyne through the reaction of stereodefined fully substituted silyl ketene hemiaminal derivatives with Selectfluor.

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Ando, Shinji, Yoshihara Terui, Yasuhiro Aiki, and Takahiro Ishizuka. "Synthesis and Properties of Fully Aromatic Non-fluorinated Polyimides Exhibiting High Transparency and Low Thermal Expansion." Journal of Photopolymer Science and Technology 18, no. 2 (2005): 333–36. http://dx.doi.org/10.2494/photopolymer.18.333.

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Peddapuram, Adithya, Hammad Cheema, Louis McNamara, Yanbing Zhang, Nathan Hammer, and Jared Delcamp. "Quinoxaline-Based Dual Donor, Dual Acceptor Organic Dyes for Dye-Sensitized Solar Cells." Applied Sciences 8, no. 9 (August 21, 2018): 1421. http://dx.doi.org/10.3390/app8091421.

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A novel metal-free quinoxaline-based molecular framework with a dual donor and dual acceptor (DD-π-AA) motif has been introduced. Four sensitizers (AP6, AP8, AP9, and AP12) have been synthesized and fully characterized via UV–Vis absorption, cyclic voltammetry, density functional theory (DFT) calculations, time-correlated single photon counting (TCSPC), and in dye-sensitized solar cell (DSC) devices. Structural modifications to both the donor and acceptor/anchor regions were evaluated via structure–property relationships without altering the quinoxaline π-bridge. Through careful dye design, a broadly absorbing near-infrared (NIR) sensitizer extending electricity production to 800 nm is realized in DSC devices. Ground- and excited-state oxidation potentials were measured to show energetically favorable charge transfer events. Importantly, the dye structure was found to have a strong influence on dye energetics in different environments with structural elements allowing for either similar or dramatically different solution versus film measurements. The DSC device electrolyte was also found to have a significant influence on dye energetics as well. Electron transfer events were probed for each dye with DSC device measurements and with TCSPC studies. The results are correlated to the dye structures.

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Giesy, John P., Kurunthachalam Kannan, and Paul D. Jones. "Global Biomonitoring of Perfluorinated Organics." Scientific World JOURNAL 1 (2001): 627–29. http://dx.doi.org/10.1100/tsw.2001.342.

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The environmental distribution of fluorinated organic compounds (FOCs) has been less well described than the other halogenated hydrocarbons such as chlorinated and brominated compounds. This is despite the fact that FOCs have been used in a wide variety of products and applications for more than 50 years. FOCs are resistant to hydrolysis, photolysis, microbial degradation, or metabolism by vertebrates due to the high energy of carbon–fluorine bond. In particular, perfluorinated (fully fluorinated) compounds (PFCs) have the potential to persist in the environment. But, until recently, the extent and magnitude of environmental distribution of PFCs was unknown. Recent development of an analytical technique for PFCs using high performance liquid chromatography-negative ion electrospray tandem mass spectrometry (HPLC-ESMSMS)[1] permitted the survey of PFCs in livers and blood plasma of wildlife on a global scale[2].

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Wang, Yuqing, Gaigai Wang, Anatoly A. Peshkov, Ruwei Yao, Muhammad Hasan, Manzoor Zaman, Chao Liu, Stepan Kashtanov, Olga P. Pereshivko, and Vsevolod A. Peshkov. "Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts through the cinchona alkaloid-promoted electrophilic fluorination." Beilstein Journal of Organic Chemistry 16 (August 11, 2020): 1963–73. http://dx.doi.org/10.3762/bjoc.16.163.

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In this report, we introduce a new strategy for controlling the stereochemistry in Ugi adducts. Instead of controlling stereochemistry directly during the Ugi reaction we have attempted to stereodefine the chiral center at the peptidyl position through the post-Ugi functionalization. In order to achieve this, we chose to study 2-oxo-aldehyde-derived Ugi adducts many of which partially or fully exist in the enol form that lacks the aforementioned chiral center. This in turn led to their increased nucleophilicity as compared to the standard Ugi adducts. As such, the stereocenter at the peptidyl position could be installed and stereodefined through the reaction with a suitable electrophile. Towards this end, we were able to deploy an asymmetric cinchona alkaloid-promoted electrophilic fluorination producing enantioenriched post-Ugi adducts fluorinated at the peptidyl position.

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Leyva, Elisa, Matthew S. Platz, Silvia E. Loredo-Carrillo, and Johana Aguilar. "Fluoro Aryl Azides: Synthesis, Reactions and Applications." Current Organic Chemistry 24, no. 11 (September 11, 2020): 1161–80. http://dx.doi.org/10.2174/1385272824999200608132505.

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Background: The complex photochemistry of aryl azides has fascinated scientists for several decades. Spectroscopists have investigated the intermediates formed by different analytical techniques. Theoretical chemists have explained the intrinsic interplay of intermediates under different experimental conditions. Objective & Method: A complete understanding of the photochemistry of a given fluoro aryl azide is a basic requisite for its use in chemistry. In this review, we will discuss the synthesis of several fluoro substituted aryl azides and the reactions and intermediates generated upon photolysis and thermolysis of these azides and some examples of their applications in photoaffinity labeling and organic synthesis. Conclusion: In spite of the extensive research on the photochemistry of fluoro aryl azides, there are some areas that remain to be investigated. The application of this reaction in the synthesis of novel heterocyclic compounds has not been fully studied. Since fluorophenyl azides are known to undergo C-H and N-H insertion reactions, they could be used to prepare new fluorinated molecules or in the biochemical process known as photoaffinity labeling.

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Fiorenza, Dario, Emanuele Nicolai, Carlo Cavaliere, Ferdinando Fiorino, Giovanna Esposito, and Marco Salvatore. "Fully Automated Synthesis of Novel TSPO PET Imaging Ligand [18F]Fluoroethyltemazepam." Molecules 26, no. 8 (April 19, 2021): 2372. http://dx.doi.org/10.3390/molecules26082372.

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Introduction: Benzodiazepines, including temazepam are described as TSPO antagonists. In fact, TSPO was initially described as a peripheral benzodiazepine receptor (PBR) with a secondary binding site for diazepam. TSPO is a potential imaging target of neuroinflammation because there is an amplification of the expression of this receptor. Objectives: Herein, we developed a novel fluorinated benzodiazepine ligand, [18F]Fluoroethyltemazepam ([18F]F-FETEM), for positron emission tomography (PET) imaging of translocator protein (18 kDa). Methods: [18F]F-FETEM was radiolabelled with an automated synthesizer via a one-pot procedure. We conducted a [18F]F-aliphatic nucleophilic substitution of a tosylated precursor followed by purification on C18 and Alumina N SPE cartridges. Quality control tests was also carried out. Results: We obtained 2.0–3.0% decay-uncorrected radiochemical activity yield (3.7% decay-corrected) within the whole synthesis time about 33 min. The radiochemical purity of [18F]F-FETEM was over 90% by TLC analysis. Conclusions: This automated procedure may be used as basis for future production of [18F]F-FETEM for preclinical PET imaging studies.

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Risi, Guglielmo, Mariia Becker, Catherine E. Housecroft, and Edwin C. Constable. "Are Alkynyl Spacers in Ancillary Ligands in Heteroleptic Bis(diimine)copper(I) Dyes Beneficial for Dye Performance in Dye-Sensitized Solar Cells?" Molecules 25, no. 7 (March 27, 2020): 1528. http://dx.doi.org/10.3390/molecules25071528.

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The syntheses of 4,4′-bis(4-dimethylaminophenyl)-6,6′-dimethyl-2,2′-bipyridine (1), 4,4′-bis(4-dimethylaminophenylethynyl)-6,6′-dimethyl-2,2′-bipyridine (2), 4,4′-bis(4-diphenylaminophenyl)-6,6′-dimethyl-2,2′-bipyridine (3), and 4,4′-bis(4-diphenylaminophenylethynyl)-6,6′-dimethyl-2,2′-bipyridine (4) are reported along with the preparations and characterisations of their homoleptic copper(I) complexes [CuL2][PF6] (L = 1–4). The solution absorption spectra of the complexes exhibit ligand-centred absorptions in addition to absorptions in the visible region assigned to a combination of intra-ligand and metal-to-ligand charge-transfer. Heteroleptic [Cu(5)(Lancillary)]+ dyes in which 5 is the anchoring ligand ((6,6′-dimethyl-[2,2′-bipyridine]-4,4′-diyl)bis(4,1-phenylene))bis(phosphonic acid) and Lancillary = 1–4 have been assembled on fluorine-doped tin oxide (FTO)-TiO2 electrodes in dye-sensitized solar cells (DSCs). Performance parameters and external quantum efficiency (EQE) spectra of the DSCs (four fully-masked cells for each dye) reveal that the best performing dyes are [Cu(5)(1)]+ and [Cu(5)(3)]+. The alkynyl spacers are not beneficial, leading to a decrease in the short-circuit current density (JSC), confirmed by lower values of EQEmax. Addition of a co-absorbent (n-decylphosphonic acid) to [Cu(5)(1)]+ lead to no significant enhancement of performance for DSCs sensitized with [Cu(5)(1)]+. Electrochemical impedance spectroscopy (EIS) has been used to investigate the interfaces in DSCs; the analysis shows that more favourable electron injection into TiO2 is observed for sensitizers without the alkynyl spacer and confirms higher JSC values for [Cu(5)(1)]+.

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Huang, Xiaohua, Hua Li, Chanjuan Liu, and Chun Wei. "Design and synthesis of high heat-resistant, soluble, and hydrophobic fluorinated polyimides containing pyridine and trifluoromethylthiophenyl units." High Performance Polymers 31, no. 1 (December 26, 2017): 107–15. http://dx.doi.org/10.1177/0954008317749018.

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In this study, a novel diamine monomer, 4-(4-trifluoromethylthiophenyl)-2,6-bis(4-aminophenyl)pyridine (FTPAP) was synthesized through two-step reaction from 4-trifluoromethylthiobenzaldehyde and 4-nitroacetophenone as raw materials, and then the structure of FTPAP was characterized by Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance, and mass spectrometry. A series of fluorinated polyimides were prepared from FTPAP with five commercial dianhydrides, namely, pyromellitic dianhydride, biphenyl tetracarboxylic dianhydride, oxydiphtahalic anhydride, benzophenone tetracarboxylic dianhydride, and 4,4′-(hexafluoroisopropylidene) diphthalic anhydride. The structure and performance of the fluorinated polymers were fully characterized by FTIR, differential scanning calorimetry, thermogravimetric analysis, and wide-angle X-ray diffraction (WAXD). The inherent viscosity of polymers ranged from 0.41 to 1.45 dL g−1. These polymers displayed good solubility in polar aprotic solvents, such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, and N-methyl-2-pyrrolidone, at room temperature or on heating. Furthermore, they exhibited outstanding thermal stability with glass transition temperatures beyond 305°C, and the temperature of 10% weight loss was in the range of 514–573°C with more than 56% residue at 800°C under nitrogen. Moreover, they showed high optical transparency with the cutoff wavelengths in the range of 385–457 nm and excellent hydrophobic property with contact angle in the range of 82.8–97.6°. In addition, the results of WAXD indicated that all of the polymers presented amorphous structure.

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Ang, Chwee Ying, Seah Ling Kuan, Geok Kheng Tan, Lai Yoong Goh, Tracey L. Roemmele, Xin Yu, and René T. Boeré. "Coordination complexes of thiazyl rings — Synthesis, structure, and density functional theory (DFT) computational analysis of CpCr(CO)x (x = 2, 3) complexes of fluorinated and nonfluorinated 1λ3-1,2,4,6-thiatriazinyls with differing Cr–S bond orders." Canadian Journal of Chemistry 93, no. 2 (February 2015): 181–95. http://dx.doi.org/10.1139/cjc-2014-0257.

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The reaction of [3,5-Ph2-C2N3S]2 with [CpCr(CO)3]2 in toluene at room temperature forms an adduct via a Cr–S bond, formulated as CpCr(CO)3SN3C2Ph2, which has fitting NMR, IR, and combustion analysis data. The structure was determined by a single-crystal X-ray structure diffraction study (P21/n, a = 8.4611(17) Å, b = 20.509(4) Å, c = 11.757(2) Å, β = 104.453(7)°). The Cr–S bond length of 2.4908(11) Å corresponds to a bond order of 1.0 from >90 values for CpCr(CO)x or Cp*Cr(CO)x moieties (x = 2, 3) bonded to S, which are used to establish a Pauling-type bond order scale specific to this class of compounds. Similar reactions of fluorinated thiatriazinyls derived from [3-Ph-5-CF3-C2N3S]2 or [4-MeOC6H4-5-CF3-C2N3S]2 are accompanied by the loss of CO to produce CpCr(CO)2SN3C2PhCF3 (P1, a = 8.0929(8) Å, b = 10.3160(10) Å, c = 11.2405(11) Å, α = 70.032(2)°, β = 72.076(2)°, γ = 82.375(2)°) and CpCr(CO)2SN3(CCF3)(C6H4OCH3) (P21/c, a = 8.1311(7) Å, b = 24.284(2) Å, c = 9.1025(8) Å, β = 97.218(2)°), also fully characterized by spectroscopy and crystallography. Their measured Cr–S bond lengths, 2.2987(14) and 2.2965(11) Å, correspond to bond orders of 1.5. (U/R)B3PW91/6-311+G(2df,2p)//B3PW91/6-31G(2d,p) hybrid density functional theory (DFT) calculations show that the tricarbonyl complex has an unusual σ bond. However, the dicarbonyl complexes of the fluorinated thiatriazinyls are π bonded.

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Akter, Jesmin, Jai-yeop Lee, Hyun-Ju Ha, In Geol Yi, Da-Hye Hong, Chang-Min Park, Mok-Young Lee, and Ilho Kim. "Degradation of Organics and Change Concentration in Per-Fluorinated Compounds (PFCs) during Ozonation and UV/H2O2 Advanced Treatment of Tertiary-Treated Sewage." Sustainability 14, no. 9 (May 6, 2022): 5597. http://dx.doi.org/10.3390/su14095597.

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This study aimed to investigate the effect of H2O2 addition, ozone feed rate, and UV addition on the change in the concentration of organics such as CODMn, CODCr, TOC, and PFCs in tertiary-treated effluent from a sewage treatment plant (STP) during the O3 and UV/H2O2 process. The degradation of organic pollutants from tertiary effluent is a significant challenge because biological treatment cannot degrade these recalcitrant pollutants. Therefore, the O3/UV/H2O2 process was an effective method for treating recalcitrant organics. Several batch tests were conducted to investigate the direct UV photolysis, UV/H2O2, and ozone-based advanced oxidation process to degrade CODMn, CODCr, TOC, and PFCs. The chemical oxygen demand (COD) and total organic carbon (TOC) with UV irradiation showed 95% and 50% removal efficiency percentages under optimal conditions (initial pH = 6.7, H2O2 dosage = 50 mg/L, ozone feed rate = 5.8 mg/L/min. Moreover, UV irradiation, with the addition of H2O2, and a sufficient dose of ozone, demonstrated the efficient removal of organic compounds by the indication of radical oxidation. (·OH) is the dominant mechanism. However, AOPs are not sufficient to fully treat the PFC compound; thus, additional procedures are required to degrade PFCs. In this study, the removal of organic recalcitrant contaminants and the change in added PFC concentration in tertiary-treated sewage were investigated by applying the ozone-based advanced oxidation process.

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Sfameni, Silvia, Giulia Rando, Maurilio Galletta, Ileana Ielo, Marco Brucale, Filomena De Leo, Paola Cardiano, et al. "Design and Development of Fluorinated and Biocide-Free Sol–Gel Based Hybrid Functional Coatings for Anti-Biofouling/Foul-Release Activity." Gels 8, no. 9 (August 26, 2022): 538. http://dx.doi.org/10.3390/gels8090538.

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Biofouling has destructive effects on shipping and leisure vessels, thus producing severe problems for marine and naval sectors due to corrosion with consequent elevated fuel consumption and higher maintenance costs. The development of anti-fouling or fouling release coatings creates deterrent surfaces that prevent the initial settlement of microorganisms. In this regard, new silica-based materials were prepared using two alkoxysilane cross-linkers containing epoxy and amine groups (i.e., 3-Glycidyloxypropyltrimethoxysilane and 3-aminopropyltriethoxysilane, respectively), in combination with two functional fluoro-silane (i.e., 3,3,3-trifluoropropyl-trimethoxysilane and glycidyl-2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluorononylether) featuring well-known hydro repellent and anti-corrosion properties. As a matter of fact, the co-condensation of alkoxysilane featuring epoxide and amine ends, also mixed with two opportune long chain and short chain perfluorosilane precursors, allows getting stable amphiphilic, non-toxic, fouling release coatings. The sol–gel mixtures on coated glass slides were fully characterized by FT-IR spectroscopy, while the morphology was studied by scanning electron microscopy (SEM), and atomic force microscopy (AFM). The fouling release properties were evaluated through tests on treated glass slides in different microbial suspensions in seawater-based mediums and in seawater natural microcosms. The developed fluorinated coatings show suitable antimicrobial activities and low adhesive properties; no biocidal effects were observed for the microorganisms (bacteria).

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Kui, Tony, Sébastien Livi, and Jérôme Baudoux. "Synthesis of 1-[1H,1H,2H,2H-perfluooctyl]-3-[2-(oxiran-2-yl)ethyl]imidazolium 4-[(2-oxiran-2-yl)ethoxy]benzenesulfonate as a New Perfluorinated Ionic Monomer." Molbank 2022, no. 3 (July 15, 2022): M1409. http://dx.doi.org/10.3390/m1409.

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Access to perfluorinated compounds represents a growing challenge in the academic and industrial fields to achieve target compounds with specific physico-chemical properties. Especially, the insertion of a perfluorinated chain within an ionic liquid can provide improvements not just in terms of hydrophobicity and lipophobicity, but also viscosity, density as well as thermal stability. In this research area, we have recently developed new access points to several epoxy imidazolium salts combined with fluorinated anions such as bistriflimide (NTf2−), hexafluorophosphate (PF6−) or tetrafluoroborate (BF4−). Here, we reported the synthesis of a perfluorinated imidazolium cation associated with a sulfonate anion as a new functionalized partner. This sequence required four steps from imidazole (cationic part) and three steps from sodium 4-hydroxybenzenesulfonate (anionic part), respectively. This perfluorinated ionic liquid was fully characterized by nuclear magnetic resonance with 1H-NMR, 19F-NMR, 13C-NMR, DEPT, COSY, HSQC, HMBC and IR spectroscopy. The two parts of the salt were confirmed by high-resolution mass spectrometry (HRMS), and we combined thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) to determine the thermal properties of this new compound.

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Shao, Yunqi, Yu Wang, Mao Du, Aristeidis Voliotis, M. Rami Alfarra, Simon P. O'Meara, S. Fiona Turner, and Gordon McFiggans. "Characterisation of the Manchester Aerosol Chamber facility." Atmospheric Measurement Techniques 15, no. 2 (January 31, 2022): 539–59. http://dx.doi.org/10.5194/amt-15-539-2022.

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Abstract. This study describes the design of the Manchester Aerosol Chamber (MAC), initially developed in 2005 and presents for the first time its comprehensive characterisation. The MAC is designed to investigate multi-phase chemistry and the evolution of aerosol physico-chemical properties from the real-world emissions (e.g. diesel engine, plants) or of secondary organic aerosol (SOA) produced from pure volatile organic compounds (VOCs). Additionally, the generated aerosol particles in the MAC can be transferred to the Manchester Ice Cloud Chamber (MICC), which enables investigation of cloud formation in warm, mixed-phase, and fully glaciated conditions (with temperature, T, as low as −55 ∘C). The MAC is an 18 m3 fluorinated ethylene propylene (FEP) Teflon chamber with the potential to conduct experiments at controlled temperature (15–35 ∘C) and relative humidity (RH; 25 %–80 %) under simulated solar radiation or dark conditions. Detailed characterisations were conducted at common experimental conditions (25 ∘C, 50 % RH) for actinometry and determination of background contamination, wall losses of gases (NO2, O3, and selected VOCs), aerosol particles at different sizes, chamber wall reactivity, and aerosol formation. In addition, the influences of chamber contamination on the wall loss rate of gases and particles and the photolysis of NO2 were estimated.

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Soykan, Ugur. "Role of percent grafting and chain length of fully fluorinated pendant units in the grafted acrylic compound on crucial characteristic properties of high density polyethylene." Journal of Fluorine Chemistry 236 (August 2020): 109591. http://dx.doi.org/10.1016/j.jfluchem.2020.109591.

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Hellén, Heidi, Simon Schallhart, Arnaud P. Praplan, Tuukka Petäjä, and Hannele Hakola. "Using in situ GC-MS for analysis of C<sub>2</sub>–C<sub>7</sub> volatile organic acids in ambient air of a boreal forest site." Atmospheric Measurement Techniques 10, no. 1 (January 26, 2017): 281–89. http://dx.doi.org/10.5194/amt-10-281-2017.

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Abstract. An in situ method for studying gas-phase C2–C7 monocarboxylic volatile organic acids (VOAs) in ambient air was developed and evaluated. Samples were collected directly into the cold trap of the thermal desorption unit (TD) and analysed in situ using a gas chromatograph (GC) coupled to a mass spectrometer (MS). A polyethylene glycol column was used for separating the acids. The method was validated in the laboratory and tested on the ambient air of a boreal forest in June 2015. Recoveries of VOAs from fluorinated ethylene propylene (FEP) and heated stainless steel inlets ranged from 83 to 123 %. Different VOAs were fully desorbed from the cold trap and well separated in the chromatograms. Detection limits varied between 1 and 130 pptv and total uncertainty of the method at mean ambient mixing ratios was between 16 and 76 %. All straight chain VOAs except heptanoic acid in the ambient air measurements were found with mixing ratios above the detection limits. The highest mixing ratios were found for acetic acid and the highest relative variations for hexanoic acid. In addition, mixing ratios of acetic and propanoic acids measured by the novel GC-MS method were compared with proton-mass-transfer time-of-flight mass spectrometer (PTR-TOFMS) data. Both instruments showed similar variations, but differences in the mixing ratio levels were significant.

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Ishige, Ryohei, Noboru Ohta, Hiroki Ogawa, Masatoshi Tokita, and Atsushi Takahara. "Fully Liquid-Crystalline ABA Triblock Copolymer of Fluorinated Side-Chain Liquid-Crystalline A Block and Main-Chain Liquid-Crystalline B Block: Higher Order Structure in Bulk and Thin Film States." Macromolecules 49, no. 16 (August 2, 2016): 6061–74. http://dx.doi.org/10.1021/acs.macromol.6b00855.

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Ul Mushtaq, Ameeq, Jörgen Ådén, Tobias Sparrman, Mattias Hedenström, and Gerhard Gröbner. "Insight into Functional Membrane Proteins by Solution NMR: The Human Bcl-2 Protein—A Promising Cancer Drug Target." Molecules 26, no. 5 (March 8, 2021): 1467. http://dx.doi.org/10.3390/molecules26051467.

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Evasion from programmed cell death (apoptosis) is the main hallmark of cancer and a major cause of resistance to therapy. Many tumors simply ensure survival by over-expressing the cell-protecting (anti-apoptotic) Bcl-2 membrane protein involved in apoptotic regulation. However, the molecular mechanism by which Bcl-2 protein in its mitochondrial outer membrane location protects cells remains elusive due to the absence of structural insight; and current strategies to therapeutically interfere with these Bcl-2 sensitive cancers are limited. Here, we present an NMR-based approach to enable structural insight into Bcl-2 function; an approach also ideal as a fragment-based drug discovery platform for further identification and development of promising molecular Bcl-2 inhibitors. By using solution NMR spectroscopy on fully functional intact human Bcl-2 protein in a membrane-mimicking micellar environment, and constructs with specific functions remaining, we present a strategy for structure determination and specific drug screening of functional subunits of the Bcl-2 protein as targets. Using 19F NMR and a specific fragment library (Bionet) with fluorinated compounds we can successfully identify various binders and validate our strategy in the hunt for novel Bcl-2 selective cancer drug strategies to treat currently incurable Bcl-2 sensitive tumors.

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Lindič, Tilen, Anthony Schulz, and Beate Paulus. "First-Principle Investigation of Hypothetical NiF4 Crystal Structures." Crystals 12, no. 11 (November 15, 2022): 1640. http://dx.doi.org/10.3390/cryst12111640.

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An important synthetic route for the fluorinated organic compounds is electrochemical fluorination (ECF). This is a process taking place on a nickel anode immersed in anhydrous HF. Even though the mechanism is not fully resolved, it is believed that it involves higher valent nickel fluorides formed on the anode. One such compound could be NiF4. Its synthesis and existence have been reported in the literature. However, its crystal structure has so far remained unknown. In this paper, we present, for the first time, the theoretical study of the possible crystal structure of NiF4. We investigated six crystal structures of known metal tetrafluorides as possible candidates for NiF4 by periodic DFT, with the PBE+U method. Of the investigated structures, the most stable polymorph of NiF4 was found to be of the same crystal structure as RuF4. The unit cell parameters were calculated to be a = 4.80 Å, b = 5.14 Å, c = 5.18 Å and β = 105.26∘. All but one of the investigated structures feature octahedrally coordinated nickel centers with two non-bridging fluorine atoms. In the structure originating from ZrF4, all six fluorine atoms around the nickel centers are bridging and two are located in the vacancies around the nickel skeleton, not directly bound to nickel. The overall magnetic arrangement in all the investigated structures is antiferromagnetic. A comparison with other binary nickel fluorides supports the experimental findings that NiF4 is thermodynamically the least stable.

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Kunacheva, Chinagarn, Shuhei Tanaka, Shigeo Fujii, Suwanna Kitpati Boontanon, Chanatip Musirat, and Thana Wongwattana. "Determination of perfluorinated compounds (PFCs) in solid and liquid phase river water samples in Chao Phraya River, Thailand." Water Science and Technology 64, no. 3 (August 1, 2011): 684–92. http://dx.doi.org/10.2166/wst.2011.686.

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Perfluorinated compounds (PFCs), especially perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA), are fully fluorinated organic compounds, which have been used in many industrial applications. These chemicals have contaminated surface water all over the world even in developing countries like Thailand. The previous study showed the contamination in Chao Phraya River in 2006 and 2007. The purposes of this field study were to determine the solid and liquid phase of PFCs contamination in Chao Phraya River and to compare the changes of PFC concentration in 2008. Surveys were conducted in the lower reach of Chao Phraya River in the industrialized area. A solid phase extraction (SPE) coupled with HPLC-ESI-MS/MS were used for the analysis for ten PFCs. Ten PFCs were analyzed to identify the contamination in both solid and liquid phases. PFCs were detected in both the solid and liquid phase in every sample. PFOA was the most dominant PFC while PFPA and PFOS were also highly detected in most samples. The average loadings of PFPA, PFOA and PFOS in Chao Phraya River were 94.3, 284.6 and 93.4 g/d, respectively. PFOS concentrations did not show differences between 2006 and 2008. However, PFOA concentrations were higher in 2008/5/26, while comparing other samplings. The ratio of solid : liquid PFPA (2.1 : 1.0) [(ng/g)/(ng/L)] was lower than PFOA (13.9 : 1.0) [(ng/g)/(ng/L)] and PFOS (17.6 : 1.0) [(ng/g)/(ng/L)]. The shorter chain (more hydrophilic) PFC was better to dissolve in water rather than adsorb onto suspended solids. PFOS also showed more potential to attach in the suspended solids than PFOA.

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Hemming, Jocelyn D. C., Mark Hosford, and Martin M. Shafer. "Application of the direct peptide reactivity assay (DPRA) to inorganic compounds: a case study of platinum species." Toxicology Research 8, no. 6 (November 1, 2019): 802–14. http://dx.doi.org/10.1039/c9tx00242a.

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Abstract The in chemico Direct Peptide Reactivity Assay (DPRA) was developed as a non-animal, relatively high throughput, screening tool for skin sensitization potential. Although the Adverse Outcome Pathway (AOP) for respiratory sensitization remains to be fully elucidated, it is recognized that the molecular initiation event for both skin and respiratory sensitization to low molecular weight chemicals involves haptenation with proteins. The DPRA examines the reactivity of a test compound to two model peptides (containing either cysteine or lysine) and consequently is able to screen for both skin and respiratory sensitization potential. The DPRA was primarily developed for and validated with organic compounds and assessment of the applicability of the assay to metal compounds has received only limited attention. This paper reports the successful application of the DPRA to a series of platinum compounds, including hexachloroplatinate and tetrachloroplatinate salts, which are some of the most potent chemical respiratory sensitizers known. Eleven platinum compounds were evaluated using the DPRA protocol as detailed by Lalko et al., with only minor modification. Two palladium compounds with structures similar to that of the platinum species studied and cobalt chloride were additionally tested for comparison. The hexachloroplatinate and tetrachloroplatinate salts showed exceptionally high reactivity with the cysteine peptide (EC15 values of 1.4 and 14 μM, respectively). However, for platinum compounds (e.g. hydrogen hexahydroxyplatinate and tetraammineplatinum) where clinical and epidemiological evidence indicates limited sensitization potential, the cysteine DPRA showed only minor or no reactivity (EC15 values of 24 600 and >30 000 μM, respectively). The outcomes of the lysine peptide assays were less robust and where EC15 was measurable, values were substantially higher than the corresponding results from the cysteine assay. This work supports the value of in chemico peptide reactivity as a metric for assessment of platinum sensitization potential and therefore in screening of new platinum compounds for low or absent sensitization potential. Additional studies are required to determine whether the DPRA may be successfully applied to other metals. We provide details on method modifications and precautions important to the success of the DPRA in the assessment of metal reactivity.

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Warren, Ross, Alberto Privitera, Pascal Kaienburg, Andreas E. Lauritzen, Oliver Thimm, Jenny Nelson, and Moritz K. Riede. "Controlling energy levels and Fermi level en route to fully tailored energetics in organic semiconductors." Nature Communications 10, no. 1 (December 2019). http://dx.doi.org/10.1038/s41467-019-13563-x.

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AbstractSimultaneous control over both the energy levels and Fermi level, a key breakthrough for inorganic electronics, has yet to be shown for organic semiconductors. Here, energy level tuning and molecular doping are combined to demonstrate controlled shifts in ionisation potential and Fermi level of an organic thin film. This is achieved by p-doping a blend of two host molecules, zinc phthalocyanine and its eight-times fluorinated derivative, with tunable energy levels based on mixing ratio. The doping efficiency is found to depend on host mixing ratio, which is explained using a statistical model that includes both shifts of the host’s ionisation potentials and, importantly, the electron affinity of the dopant. Therefore, the energy level tuning effect has a crucial impact on the molecular doping process. The practice of comparing host and dopant energy levels must consider the long-range electrostatic shifts to consistently explain the doping mechanism in organic semiconductors.

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Zhou, Xiang, Andreas Nollau, Jan Blochwitz, Martin Pfeiffer, Torsten Fritz, and Karl Leo. "Low Driving Voltage of Organic Light-Emitting Diodes Using p-Doping Starburst Amine as Hole Transporter." MRS Proceedings 660 (2000). http://dx.doi.org/10.1557/proc-660-jj5.23.

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ABSTRACTWe investigate the electrical properties and the OLED application of controlledly doped amorphous hole transporters. Thin films of starburst amine, 4,4',4“-tris(N,N-diphenyl- amino) triphenylamine (TDATA), doped by a fully fluorinated form of tetracyano- quinodimethane (F4-TCNQ), are characterized in situ by temperature dependent conductivity and Seebeck measurements. The conductivity and hole concentration increase with dopant concentration and are many orders of magnitude higher than those of undoped material. OLED devices with the layer sequence ITO/TDATA(200 nm)/Alq3(65 nm)/LiF(1 nm)/Al were fabricated. The use of p-doped TDATA thin films with high bulk conductivity and hole concentration reduces the resistance of the devices and leads to a thinner space charge layer which facilitates injection of holes from the ITO anode.

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Balaraman, Kaluvu, and Christian Wolf. "Chemodivergent Csp ³ ─F bond functionalization and cross-electrophile alkyl-alkyl coupling with alkyl fluorides." Science Advances 8, no. 21 (May 27, 2022). http://dx.doi.org/10.1126/sciadv.abn7819.

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The widespread use of fluorinated organic compounds in the health, agrochemical, and materials sciences is sustained by a steadily growing pool of commercially available fine chemicals. The synthetic utility of the increasingly ubiquitous Csp 3 ─F bond, however, remains to be fully exploited, which is often a difficult task because of its paramount stability and chemical inertness. Here, we demonstrate chemodivergent activation of monofluoroalkyl compounds toward either nucleophilic or electrophilic intermediates. This is accomplished under conditions that are compatible with several reaction types and many functional groups, which drastically widens the current scope of organofluorine chemistry and sets the stage for carbon-carbon and carbon-heteroatom bond formations, stereoselective construction of bisoxindole alkaloid scaffolds via in situ Umpolung, and cross-electrophilic coupling methodology. The selective generation of either nucleophilic or electrophilic species and the possibility of doing so simultaneously or, alternatively, switching molecular polarity enable previously unidentified synthetic opportunities that recognize alkyl fluorides as chemodivergent building blocks.

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Eryilmaz, Kurtulus, and Benan Kilbas. "A practical fully automated radiosynthesis of [18F]Flurpiridaz on the module modular lab-pharmtracer without external purification." EJNMMI Radiopharmacy and Chemistry 7, no. 1 (November 5, 2022). http://dx.doi.org/10.1186/s41181-022-00182-z.

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Abstract Background [18F]Flurpiridaz is a promising novel cardiac PET imaging tracer formed by the radiolabeling of pyridaben derivative with fluorine-18. Clinical studies on [18F]Flurpiridaz are currently at the phase III level for the assessment of MPI. Providing high image quality thanks to its relatively long half-life, F-18 is a high-potential radionuclide for the early detection of CAD. In this study, we aimed to develop a fully automated synthesis of [18F]Flurpiridaz without further preparative HPLC purification. Results Precursor 6 was obtained by multi-step synthesis starting from mucochloric acid (1) as a sole product with 35% yield and identified by spectroscopic measurement. Manually cold labeling experiments were performed using the stable isotope [19F]F, and TBA-HCO3 PTC provided desirable fluorinated compound with high yield. A fully automated [18F]Flurpiridaz synthesis on the ML-PT device provided 55–65% radiochemical yield with more than 98% radiochemical purity. The final product purification method demonstrated that [18F]Flurpiridaz could be obtained without an external preparative HPLC system as a pharmaceutical quality. Conclusion A novel and fascinating strategy was developed for the fully automated synthesis of [18F]Flurpiridaz (7) on ML PT. Organic synthesis of precursor 6 was achieved with a desirable yield and characterized by NMR and HR-MS. A detailed set of cold experiments were completed for optimization conditions before hot trials and TBA-HCO3 increased molar activity with a minimum amount of side products. Radiolabeling showed that our self-designed automated synthesis method enables high radiochemical yield and radiochemical purity for the production of [18F]Flurpiridaz. The desirable radiopharmaceutical quality of the product was obtained without using an additional preparative HPLC system. [18F]Flurpiridaz (7) preserved its stability within 12 h and final specifications were consistent with the acceptance criteria in Ph. Eur. regulations.

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Journal articles on the topic 'Fully fluorinated organic sensitizers'

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