- Light- and heat-triggered reversible luminescent materials based on polysiloxanes with anthracene groups
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In this study, reversible silicone elastomers were successfully developed by light-triggered dimerization and heat depolymerization of the anthryl groups. Polysiloxanes with anthryl groups were prepared from poly(aminopropylmethylsiloxane) (PAPMS) with electron-donating (9-anthracenylmethyl acrylate) and electron-withdrawing (anthracene-9-carboxylic acid) units. The cross-linking networks were formed with the via 4π-4π photo-cycloadditions of the anthryl groups upon the UV light excitation (365 nm). 9-Anthracenylmethyl acrylate or anthracene-9-carboxylic acid efficiently dimerized through the photodimerization of the anthryl groups in the organic solvents, which was proven by UV-vis spectra, NMR spectra, and LC/MS. The covalent bonds between pendant anthryl groups were cleaved after heating at 120 °C. Furthermore, repeatable dimerization-depolymerization conversion was confirmed. In addition, for the first time, we found that the sunlight can also initiate the cycloaddition, which was "greener" and more environment-friendly. The green luminescence was observed from the PAPMS-1 film instead of the quenching effect caused by aggregation after the cycloaddition. Thus, a colorful UV-light emitting diode (LED) cell was obtained by coating the films on the commercially available LED cell.
- Han, Dongdong,Lu, Hang,Li, Wensi,Li, Yonghao,Feng, Shengyu
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- A Fluorescent Silver(I) Carbene Complex with Anticancer Properties: Synthesis, Characterization, and Biological Studies
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The silver(I) N-heterocyclic carbene (NHC) complex bis(1-(anthracen-9-ylmethyl)-3-ethylimidazol-2-ylidene) silver chloride ([Ag(EIA)2]Cl), bearing two anthracenyl fluorescent probes, has been synthesized and characterized. [Ag(EIA)2]Cl is stable in organic solvents and under physiological conditions, and shows potent cytotoxic effects in vitro toward human SH-SY5Y neuroblastoma cells. The interactions of [Ag(EIA)2]Cl with a few model biological targets have been studied as well as its ability to be internalized in cells. The in vitro anticancer activity is apparently related to the level of drug internalization. Notably, [Ag(EIA)2]Cl does not react with a few model proteins, but is capable of binding the C-terminal dodecapeptide of thioredoxin reductase hTrxR(488–499) and to strongly inhibit the activity of this enzyme. Binding occurs through an unconventional process leading to covalent binding of one or two carbene ligands to the C-terminal dodecapeptide with concomitant release of the silver cation. To the best of our knowledge, this mode of interaction is reported here for the first time for Ag(NHC)2 complexes.
- Fabbrini, Maria Giulia,Cirri, Damiano,Pratesi, Alessandro,Ciofi, Lorenzo,Marzo, Tiziano,Guerri, Annalisa,Nistri, Silvia,Dell'Accio, Alfonso,Gamberi, Tania,Severi, Mirko,Bencini, Andrea,Messori, Luigi
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- A simple and robust PET-based anthracene-appended O-N-O chelate for sequential recognition of Fe3+/CN– ions in aqueous media and its multimodal applications
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A very simple, robust, and pico/nanomolar-sensitive 9,10-diethanolamine-substituted fluorescent Fe3+/CN– probe (PD) was synthesised, and its sensing abilities towards various ions were studied in mixed aqueous media. PD selectively recognised Fe3+ ions through a ‘turn on’ response with an excellent binding constant (Ka, 9.29 × 106 M?1) in 1:2 binding stoichiometry at pH 7.0 in phosphate-buffered saline (PBS). The in situ generated Fe3+·PD ensemble sequentially recognised CN– ions with an excellent binding constant (Ka 1.72 × 108 M?1) via a ‘turn off’ mode by extruding Fe3+ ions from the ensemble. The highly selective sequential ‘on-off’ responses towards Fe3+ and CN– ions were attributed to inhibition and restoration of photoinduced electron transfer (PET) and chelation-induced enhanced fluorescence (CHEF) effects from the chelating N and O heteroatoms. PD was able to detect Fe3+ and CN– ions in real water samples satisfactorily at picomolar to sub-nanomolar levels. A colorimetric assay based on pyrocatechol violet (PCV) was also able to detect Fe3+/CN– in a sequential manner (up to sub-micromolar level) by a change in colour from colourless to yellow/pale green without any interferences from other ions. Based on the complexation and decomplexation mechanism, bio-imaging photonic INHIBIT logic circuit strips were prepared for use under physiological conditions. In addition, solid-phase recognition of Fe3+/CN– ions was demonstrated using cost-effective paper-based strips.
- Pandith, Anup,Choi, Jun-Hyeak,Jung, Ok-Sang,Kim, Hong-Seok
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- Synthesis of 9-Substituted Triptycene Building Blocks for Solid-Phase Diversification and Nucleic Acid Junction Targeting
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Triptycenes have been shown to bind nucleic acid three-way junctions, but rapid and efficient methods to diversify the triptycene core are lacking. An efficient synthesis of a 9-substituted triptycene scaffold is reported that can be used as a building block for solid-phase peptide synthesis and rapid diversification. The triptycene building block was diversified to produce a new class of tripeptide-triptycenes, and their binding abilities toward d(CAG)·(CTG) repeat junctions were investigated.
- Yoon, Ina,Suh, Sung-Eun,Barros, Stephanie A.,Chenoweth, David M.
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- Activation of promutagens by endogenous and heterologous sulfotransferases expressed in continuous cell cultures
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various environmental chemical are metabolised to chemically reactive sulfuric acid esters, which may covalently bind to cellular macromoleculaes and induce mutations and tumours. This activation pathway is usually not taken into account in external xenobiotic-metabolising systems used in short-term tests. We therefore analysed the abilities of cytosols from mammalian cell lines to activate benzylic alcohols (1-hydroxymethylpyrene and 9-hydroxymethylanthracene) to mutagens detectable in Salmonella typhimurium TA98. No activation was observed in cell lines which are commonly used in mutagenicity and cell transformation assays, and only low activities were found in epithelial cell lines in culture. We have therefore constructed Chineses hamster V79-derived cell lines which stably express a heterologous sulfotransferase, rat hydroxysteroid sulfotransferase a. Cytosol of these cells effectively activated 1-hydroxymethylpyrene and 9-hydroxymethylanthracene to mutagens detected in S. pyphimurium. The hepatocarcinogen 6-hydroxymethylbenzopyrene induced gene mutations in sulfotransferase-expressing V79-derived cells, whereas it elicited only marginal effects in sulfotransferase-deficient control cells. The new cell lines may allow the detection of novel classes of mutagens, since some externally generated reactive sulfuric acid esters may not readily penetrate target cells due to their short life span and their ionization. - Keywords: Benzylic alcohols; Bioactivation; Sulfotransferase; Sulfuric acid esters; V79 cells
- Glatt, Hansruedi,Pauly, Karin,Piee-Staffa, Andrea,Seidel, Albrecht,Hornhardt, Sabine,Czich, Andreas
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- Preparation and characterisation of fluorescent chitosans using 9-anthraldehyde as fluorophore
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Chitosans with chemical composition ranging from a fraction of N-acetylated units (FA) of 0.01 to 0.61 were used to prepare fluorescence labelled chitosans by reductive amination with 9-anthraldehyde. Fluorescent chitosans with a low theoretical degree of substitution (DS, 0.001-1%) were prepared, and the actual DS of the products were determined by UV and 1H NMR spectroscopy. The fluorescence excitation and emission spectra of the chitosan with FA of 0.09 and DS 1% showed an excitation maximum at 254 nm and an emission maximum at 413 nm. The intrinsic viscosities ([η]) of the fluorescent chitosans were compared to those of the original chitosans, showing that the derivatisation procedure lead only to a negligible decrease in [η]. The conformation of these fluorescent chitosans with very low DS-values is not altered and they can conveniently be directly quantified by UV or fluorescence spectroscopy.
- Tommeraas, Kristoffer,Strand, Sabina P.,Tian, Wei,Kenne, Lennart,Varum, Kjell M.
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- Experimental and DFT studies on the vibrational and electronic spectra of 9-anthracenemethanol
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Vibrational spectral measurements were made for 9-anthracenemethanol. Optimized geometrical structure and harmonic vibration frequencies were computed based on ab initio and density functional theory B3LYP methods using 6-311G and LANL2DZ basis sets. The
- Kou, Shanshan,Zhou, Hu,Tang, Guodong,Li, Rongqing,Zhang, Yu,Zhao, Jianying,Wei, Changmei
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- A Photo-Triggered Traceless Staudinger–Bertozzi Ligation Reaction
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The use of light to control the course of a chemical/biochemical reaction is an attractive idea because of its ease of administration with high precision and fine spatial resolution. Staudinger ligation is one of the commonly adopted conjugation processes that involve a spontaneous reaction between azides and arylphosphines to form iminophosphoranes, which further hydrolyze to give stable amides. We designed an anthracenylmethyl diphenylphosphinothioester (1) that showed promising Staudinger ligation reactivity upon photo-excitation. Broadband photolysis at 360–400 nm in aqueous organic solvents induced heterolytic cleavage of its anthracenylmethyl–phosphorus bond, releasing a diphenylphosphinothioester (2) as an efficient traceless Staudinger–Bertozzi ligation reagent. The quantum yield of such a photo-induced heterolytic bond-cleavage at the optimal wavelength of photolysis (376 nm) at room temperature is ≥0.07. This work demonstrated the feasibility of photocaging arylphosphines to realize the photo-triggering of the Staudinger ligation reaction.
- Hu, Peng,Feng, Tianshi,Yeung, Chi-Chung,Koo, Chi-Kin,Lau, Kai-Chung,Lam, Michael H. W.
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- Fluorometric analysis of borohydrides based on reductive aldehyde-to-alcohol conversion of arylaldehydes
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Fluorometric analysis of borohydride (BH4 –) species by the reduction of arylaldehydes to the corresponding arylmethanols was investigated. 9-Anthracenecarboxaldehyde (9-AA) exhibited pronounced ratiometric fluorescence signaling behavior toward borohydride in alkaline aqueous media. The borohydride-selective signaling of 9-AA was unaffected by the presence of commonly encountered metal ions and anions. 1-Pyrenecarboxaldehyde (1-PA) also showed comparable borohydride signaling behavior. The detection limit was found to be 7.4 μM (0.11 ppm) for 9-AA and 15.7 μM (0.23 ppm) for 1-PA. The utility of the probe with μPAD as a convenient tool for the determination of borohydrides was demonstrated.
- Kim, Na Yeong,Baek, Ji Hye,Chang, Suk-Kyu
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- The synthesis of a new type of anthracene DNA intercalator
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A new type of DNA intercalator based on anthracene 3 was synthesized. Preliminary binding studies show high affinity of this probe to CT-DNA. Higher binding constant of this compound (4.0 x 104 M-1) as compared with that known for 9-aminomethylanthracene, is caused presumably by enhanced electrostatic interaction.
- Ostaszewski, Ryszard,Wilczynska, Edyta,Wolszczak, Marian
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- An easy synthesis of lepidopterene from 9-chloromethyl anthracene. Evidence for a free radical mechanism
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This communication reports a novel and efficient synthesis of lepidopterene from 9-(chloromethyl)anthracene. Furthermore, the radical nature of the process is unambiguously established through the obtention of several 9-anthracenemethyl derivatives, which are formed via a common 9-anthracenemethyl radical intermediate, derived from 9-(iodomethyl)anthracene.
- Fernández, María-José,Gude, Lourdes,Lorente, Antonio
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- Aromatic thioesters as protecting groups for thiols against 1,2-didehydrobenzenes
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Divalent sulfur compounds usually react with 1,2-didehydrobenzenes to give a palette of unspecific products. To identify a suitable protecting group for thiols under the reaction conditions typically used for the synthesis of triptycenes, that is, 1,2-didehydrobenzene generated in situ from 2-diazoniobenzenecarboxylate at elevated temperatures, a wide-ranging optimization study was conducted. Of several acyl groups investigated, the benzoyl group turned out to be optimal. The efficiency of this protecting group was demonstrated by the successful transformation of an electron-poor (thus unreactive) anthracene derivative to the corresponding triptycenethiol derivative. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Fowelin, Christian,Schuepbach, Bjoern,Terfort, Andreas
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- Synthesis of a New Fluorescent Probe Specific for Catechols
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(Matrix Presented) The synthesis of a new fluorescent probe, specific for the cathechol moiety, has been conducted by preparation of α,α-dibromomalonamides containing an appropriate fluorophore. N,N′-Bis-anthracen-9-ylmethyl-2,2-dibromomalonamide reacted with various catechols in the presence of cesium carbonate to generate highly fluorescent derivatives.
- Stack, Douglas E.,Hill, Anastacia L.,Diffendaffer, Clark B.,Burns, Nicole M.
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- Synthesis of corrole-fullerene dyads via [4 + 2] cycloaddition reaction
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Three corrole-fullerene dyads were prepared by treating anthracene-functionalized corroles with fullerene. Their structures were characterized by 1D- and 2D-NMR spectra and mass spectra. In the preliminary photo physical study of 3a by fluorescence spectroscopy, the excited corrole unit was quenched due to the introduction of fullerene. TD-DFT calculation theoretically indicated that the electron transfer occurs from the excited corrole to fullerene. This journal is
- Li, Chengjie,Zhang, Jie,Liu, Xiujun,Zhou, Yongzhu,Sun, Dongming,Cheng, Ping,Zhang, Bao,Feng, Yaqing
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- [60]Fullerene adducts with 9-substituted anthracenes: Mechanochemical preparation and retro Diels-Alder reaction
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Three 9-substituted anthracene derivatives, that is, 9- hydroxymethylanthracene (2), 9-methoxymethylanthracene (3) and bis(9-anthrylmethyl) adipate (6), were chosen as the model compounds to evaluate the reactivity in their Diels-Alder reactions with [60]
- Wang, Guan-Wu,Chen, Zhong-Xiu,Murata, Yasujiro,Komatsu, Koichi
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- Arene-ruthenium complexes with 2-(arylazo)phenol as ancillary ligand: Synthesis, characterization, and utilization in catalytic transfer-hydrogenation
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Reaction of 2-(arylazo)phenols (HL-R, where H represents the phenolic proton and, R = CH3, H and Cl) with [{Ru(p-cymene)Cl2}2] in the presence of triethylamine affords a group of three reddish-brown complexes of type [Ru(p-cymene)(L-R)Cl] in good yields. Structure of [Ru(p-cymene)(L-CH3)Cl] has been determined by X-ray crystallography. The 2-(arylazo)phenolate ligand (L-R) is coordinated to the metal center as a mono-anionic bidentate N,O-donor forming five-membered chelate ring. All the complexes are diamagnetic, and show characteristic 1H NMR signals. They also show intense absorptions in the visible and ultraviolet regions, which have been analyzed by TDDFT calculations. Cyclic voltammetry on the complexes shows two successive irreversible oxidations within 1.10–1.40 V versus SCE. The [Ru(p-cymene)(L-R)Cl] complexes are found to serve as efficient catalyst-precursor for the transfer-hydrogenation of aldehydes.
- Karmakar, Jit,Bhattacharya, Samaresh
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- Chemical syntheses of novel fluorescent labelled fatty acids, phosphatidylcholines and cholesterol esters
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The synthesis of a novel class of fluorescent labelled fatty acids of different chain lengths and unsaturation, phospholipids and cholesterol esters has been developed. The following ω anthracene labelled cis unsaturated fatty acids have been synthesized: ω (9 anthryl) 6c octenoic, 7c nonenoic, 10c dodecenoic, 6c,9c undecadienoic, 10c,13c pentadecadienoic acid. They have been introduced into the 2 position of 1 stearoyl and 1 linoleoyl 3 sn glycerophosphocholine and cholesterol. Mass spectroscopy, 1H NMR, IR and fluorescence spectroscopy and different chromatographic procedures have been applied to confirm and characterize their structures. The properties of the different fluorescent labelled phosphatidylcholines in monomolecular films have been determined by the Langmuir technique.
- Stoffel,Michaelis
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- Expected and unexpected photoreactions of 9-(10-)substituted anthracene derivatives in cucurbit[: N] uril hosts
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By arranging substrates in a reaction ready state through noncovalent interactions, supramolecular nanoreactors/catalysts show high selectivity and/or rate acceleration features. Herein, we report the host-guest complexation of 9-(10-)substituted anthracene derivatives (G1-G3) with cucurbit[n]uril (CB[n], n = 8, 10), and the photoreactions of these derivatives in the presence of CB[n] hosts. Both CB[10] and CB[8] showed no obvious effects on the photoreaction of 9,10-disubstituted derivative G1. For G2 and G3, CB[10] operated as either a nanoreactor or catalyst (10%) for the photodimerization of two compounds with high selectivity and high yield. However, although CB[8] formed a 1 : 2 complex with G2, as also observed with CB[10], the photosolvolysis product (9-anthracenemethanol) was obtained quantitatively after photoirradiation of the CB[8]·2G2 complex. This unexpected photosolvolysis was rationalized by a plausible catalytic cycle in which anthracene acts as a photoremovable protecting group (PPG) and the carbonium ion intermediate is stabilized by CB[8].
- Hu, Xianchen,Liu, Fengbo,Liu, Simin,Zhang, Xiongzhi,Zhao, Zhiyong
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- Porphyrin-Cored Polymer Nanoparticles: Macromolecular Models for Heme Iron Coordination
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Porphyrin-cored polymer nanoparticles (PCPNs) were synthesized and characterized to investigate their utility as heme protein models. Created using collapsible heme-centered star polymers containing photodimerizable anthracene units, these systems afford model heme cofactors buried within hydrophobic, macromolecular environments. Spectroscopic interrogations demonstrate that PCPNs display redox and ligand-binding reactivity similar to that of native systems and thus are potential candidates for modeling biological heme iron coordination.
- Rodriguez, Kyle J.,Hanlon, Ashley M.,Lyon, Christopher K.,Cole, Justin P.,Tuten, Bryan T.,Tooley, Christian A.,Berda, Erik B.,Pazicni, Samuel
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- Small-Molecule Investigation of Diels-Alder Complexes for Thermoreversible Crosslinking in Polymeric Applications
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Combinations of dienes and dienophiles were examined in order to elicit possible combinations for thermoreversible crosslinking units. Comparison of experimental results and quantum calculations indicated that reaction kinetics and activation energy were much better prediction factors than change in enthalpy for the prediction of successful cycloaddition. Further testing on diene-dienophile pairs that underwent successful cycloaddition determined the feasibility of thermoreversibility/retro-reaction of each of the Diels-Alder compounds. Heating and testing of the compounds in the presence of a trapping agent allowed for experimental determination of reverse kinetics and activation energy for the retro-reaction. The experimental values were in good agreement with quantum calculations. The combination of chemical calculations with experimental results provided a strong insight into the structure-property relationships and how quantum calculations can be used to examine the feasibility of the thermoreversibility of new Diels-Alder complexes in potential polymer systems or to fine-tune thermoreversible Diels-Alder systems already in use.
- Rowlett, Jarrett R.,Deglmann, Peter,Sprafke, Johannes,Roy, Nabarun,Mülhaupt, Rolf,Bruchmann, Bernd
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p. 8933 - 8944
(2021/07/20)
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- PHOTOLYTIC COMPOUNDS AND TRIPLET-TRIPLET ANNIHILATION MEDIATED PHOTOLYSIS
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The invention provides novel photolytic compounds and prodrugs, nanoparticles and compositions thereof, and methods of conducting photolysis mediated by triplet-triplet annihilation.
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Paragraph 0026
(2021/04/17)
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- BiCl3-Facilitated removal of methoxymethyl-ether/ester derivatives and DFT study of -O-C-O- bond cleavage
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A simple method for the cleavage of methoxymethyl (MOM)-ether and ester derivatives using bismuth trichloride (BiCl3) is described. The alkyl, alkenyl, alkynyl, benzyl and anthracene MOM ether derivatives, as well as MOM esters of both aliphatic and aromatic carboxylic acids, were deprotected in good yields. To better understand the molecular roles of BiCl3and water for MOM cleavage, two possible binding pathways were investigated using the density functional theory (DFT) method. The theoretical results indicate the differential initial binding site preferences of phenolic and alcoholic MOM substrates to the Bi atom and suggest that water plays a key role in facilitating the cleavage of the MOM group.
- Pacherille, Angela,Tuga, Beza,Hallooman, Dhanashree,Dos Reis, Isaac,Vermette, Mélodie,Issack, Bilkiss B.,Rhyman, Lydia,Ramasami, Ponnadurai,Sunasee, Rajesh
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supporting information
p. 7109 - 7116
(2021/05/03)
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- Dual utility of a single diphosphine-ruthenium complex: A precursor for new complexes and, a pre-catalyst for transfer-hydrogenation and Oppenauer oxidation
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The diphosphine-ruthenium complex, [Ru(dppbz)(CO)2Cl2] (dppbz = 1,2-bis(diphenylphosphino)benzene), where the two carbonyls are mutually cis and the two chlorides are trans, has been found to serve as an efficient precursor for the synthesis of new complexes. In [Ru(dppbz)(CO)2Cl2] one of the two carbonyls undergoes facile displacement by neutral monodentate ligands (L) to afford complexes of the type [Ru(dppbz)(CO)(L)Cl2] (L = acetonitrile, 4-picoline and dimethyl sulfoxide). Both the carbonyls in [Ru(dppbz)(CO)2Cl2] are displaced on reaction with another equivalent of dppbz to afford [Ru(dppbz)2Cl2]. The two carbonyls and the two chlorides in [Ru(dppbz)(CO)2Cl2] could be displaced together by chelating mono-anionic bidentate ligands, viz. anions derived from 8-hydroxyquinoline (Hq) and 2-picolinic acid (Hpic) via loss of a proton, to afford the mixed-tris complexes [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], respectively. The molecular structures of four selected complexes, viz. [Ru(dppbz)(CO)(dmso)Cl2], [Ru(dppbz)2Cl2], [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], have been determined by X-ray crystallography. In dichloromethane solution, all the complexes show intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the complexes shows redox responses within 0.71 to -1.24 V vs. SCE. [Ru(dppbz)(CO)2Cl2] has been found to serve as an excellent pre-catalyst for catalytic transfer-hydrogenation and Oppenauer oxidation.
- Mukherjee, Aparajita,Bhattacharya, Samaresh
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p. 15617 - 15631
(2021/05/19)
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- Reduction of Aldehydes with Formic acid in Ethanol using Immobilized Iridium Nanoparticles on a Triazine-phosphanimine Polymeric Organic Support
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A novel triazine-phosphanimine polymeric organic support (TPA) was synthesized successfully by a controllable one-pot method using melamine (1,3,5-triazine-2,4,6-triamine) and trichlorophosphane (PCl3). The TPA substrate is a material incorporating P and N atoms which can coordinate with metals as a pincer ligand to stabilize them, providing an efficient heterogeneous support to prepare recyclable transition metal catalyst systems. In this study, TPA was used as support to immobilize iridium nanoparticles in the range of ~8 nm on its surface, resulting in the generation of a novel iridium nanocatalyst system (INP-TPA-POP). This catalyst system was characterized using different microscopic and spectroscopic techniques such as FT-IR, TEM, XPS, XRD, SEM, EDX, elemental analysis, ICP and BET analysis. The INP-TPA-POP nanocatalyst exhibited remarkable activity in reduction of aldehydes to alcohols using formic acids as reducing agent in ethanol as solvent.
- Panahi, Farhad,Haghighi, Fatemeh,Khalafi-Nezhad, Ali
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- Design, synthesis and application of pinenyl chiral olefin and carbene ligand
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The invention discloses design, synthesis and application of pinenyl chiral olefin and carbene ligands. According to the carbene ligand, pinene or 9-anthraceneformaldehyde is taken as a chiral source,a corresponding bromide is obtained through a two-step reaction, then benzimidazole is taken as an initial raw material, reacts with one molecule of bromide and then reacts with the other molecule ofbromide to form a salt, and corresponding pinenyl chiral olefin and carbene ligands are obtained; the carbene ligand is used as a chiral catalyst to perform asymmetric 1, 4-addition reaction, and hasfavorable selectivity.
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Paragraph 0060; 0065-0067
(2020/11/10)
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- Heteroleptic 1,4-Diazabutadiene Complexes of Ruthenium: Synthesis, Characterization and Utilization in Catalytic Transfer Hydrogenation
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Reaction of [Ru(trpy)Cl3] with 1,4-diazabutadienes (p-RC6H4N=C(H)-(H)C=NC6H4R-p; R = OCH3, CH3, H and Cl; abbreviated as L-R) in refluxing ethanol in the presence of triethylamine has afforded a family of complexes, isolated as perchlorate salts, of type [Ru(trpy)(L-R)Cl]ClO4 [depicted as complexes 1 (R = OCH3), 2 (R = CH3), 3 (R = H) and 4 (R = Cl)]. Crystal structures of complexes 1, 2 and 4 have been determined, and structure of complex 3 has been optimized by DFT method. The 1,4-diazabutadiene ligand in each complex is bound to ruthenium as a N,N-donor forming five-membered chelate. Complexes 1–4 catalyze transfer hydrogenation of aryl aldehydes to the corresponding alcohols with high (ca. 106) TON. They are also found to catalyze transfer hydrogenation of aryl ketones to corresponding secondary alcohols, but with much less efficiency. Catalytic transfer hydrogenation of nitroarenes to the corresponding amines has also been achieved.
- Saha, Rumpa,Mukherjee, Aparajita,Bhattacharya, Samaresh
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p. 4539 - 4548
(2020/11/30)
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- Synthesis and transformations of a few 9-(pent-4-yn-1-yl)anthracene-type systems
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9-(Pent-4-yn-1-yl)anthracene-type compounds can potentially undergo intramolecular Diels-Alder (IMDA) reaction to form 9,11-annulated dibenzobarrelenes. Herein we report the synthesis and IMDA reactions of several heteroatom incorporated 9-(pent-4-yn-1-yl)anthracene-type compounds.
- Mathew, Eason M.,Devassia, Tomson,Prathapan, Sreedharan,Unnikrishnan, Perupparampil A.
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- Lanthanide aryloxides catalyzed hydroboration of aldehydes and ketones
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The lanthanide aryloxides Ln(OAr)3(THF)2 (Ar = Ar1 = 2,6-tBu2-4-MeC6H2, Ln = Yb (1), Y (2); Ar = Ar2 = 2,6-iPr2C6H3, Ln = Y (3); Ar = Ar3 = 2,6-Me2C6H3, Ln = Y (4); Ar = Ar1, Ln = Sm (5), Nd (6)) could be served as highly efficient catalysts for the hydroboration of aldehydes and ketones with good functional group tolerance and excellent chemoselectivity. Computational studies were carried out to probe a feasible mechanism of the Ln-aryloxides catalyzed hydroboration of aldehydes/ketones.
- Zhu, Zhangye,Dai, Ping,Wu, Zhenjie,Xue, Mingqiang,Yao, Yingming,Shen, Qi,Bao, Xiaoguang
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- Oscillating Emission of [2]Rotaxane Driven by Chemical Fuel
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A molecular shuttle consisting of a dibenzo-24-crown-8 macrocycle and an axle with two degenerate peripheral triazolium stations, a central dibenzyl ammonium station, and two anthracenes stoppers was exposed to 2-cyano-2-phenylpropanoic acid as a chemical fuel. Protonation/deprotonation of the amine reversibly switches the rotaxane from a static and little emissive to a dynamic fluorescent shuttling device, the latter exhibiting rapid motion (15 kHz at 25 °C). Four fuel cycles were run.
- Ghosh, Amit,Paul, Indrajit,Adlung, Matthias,Wickleder, Claudia,Schmittel, Michael
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supporting information
p. 1046 - 1049
(2018/02/23)
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- COMPOSITIONS AND METHODS FOR REDUCTION OF KETONES, ALDEHYDES AND IMINIUMS, AND PRODUCTS PRODUCED THEREBY
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A method of producing an alcohol, comprises reducing an aldehyde or a ketone with a hydridosilatrane. The reducing is carried out with an activator.
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Paragraph 0076-0077
(2018/01/20)
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- TRIPTYCENE DERIVATIVES FOR NUCLEIC ACID JUNCTION STABILIZATION
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The present invention is directed to compositions and methods using triptycene derivatives (TCDs) for three way junctions (TWJs).
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Paragraph 00315; 00316; 00317
(2017/04/11)
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- Efficient Water Reduction with sp3-sp3 Diboron(4) Compounds: Application to Hydrogenations, H–D Exchange Reactions, and Carbonyl Reductions
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A series of crystalline sp3-sp3 diboron(4) compounds were synthesized and shown to promote the facile reduction of water with dihydrogen formation. The application of these diborons as simple and effective dihydrogen and dideuterium sources was demonstrated by conducting a series of selective reductions of alkynes and alkenes, and hydrogen–deuterium exchange reactions using two-chamber reactors. Finally, as the water reduction reaction generates an intermediate borohydride species, a range of aldehydes and ketones were reduced by using water as the hydride source.
- Flinker, Mathias,Yin, Hongfei,Juhl, René W.,Eikeland, Espen Z.,Overgaard, Jacob,Nielsen, Dennis U.,Skrydstrup, Troels
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supporting information
p. 15910 - 15915
(2017/11/23)
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- Aluminum Monohydride Catalyzed Selective Hydroboration of Carbonyl Compounds
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The well-defined aluminum monohydride compound [{(2,4,6-Me3-C6H2)NC(Me)}2(Me)(H)]AlH·(NMe2Et) (1) catalyzes hydroboration of a wide range of aldehydes and ketones under mild reaction conditions. Moreover, compound 1 displayed chemoselective hydroboration of aldehydes over ketones at rt.
- Jakhar, Vineet Kumar,Barman, Milan Kr.,Nembenna, Sharanappa
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supporting information
p. 4710 - 4713
(2016/09/28)
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- New anthracene-based-phtalocyanine semi-conducting materials: Synthesis and optoelectronic properties
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A new anthracene-based semi-conducting phtalocyanines AnPc and AnPc-Tr were synthesized in solvent-free conditions. The supramolecular structure of these compounds was confirmed by NMR and FT-IR spectroscopies. Their optical properties were investigated by UV-vis and photoluminescence spectroscopies. The optical gaps were estimated from the absorption-onsets films, and the obtained values were of 1.50 eV and 1.47 eV for AnPc-Tr and AnPc respectively. In solid state, a weaker π-π-interactions of conjugated systems were obtained in the case of AnPc-Tr in comparison with AnPc. This behavior was explained by steric hindrance of triazol groups, which decrease the planarity of macromolecular structure. The HOMO and LUMO levels were estimated using cyclic voltammetry analysis; two phtalocyanine derivatives show a comparable ionization potential. The phtalacyanine containing triazole groups (AnPc-Tr) reveals a higher electron affinity in comparison with AnPc. Single-layer diode devices were fabricated and showed relatively low turn-on voltages.
- Kahouech,Hriz,Touaiti,Bassem
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p. 144 - 154
(2015/12/12)
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- Silatrane as a Practical and Selective Reagent for the Reduction of Aryl Aldehydes to Benzylic Alcohols
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Hydrosilanes are cheap, readily available substrates, yet they do not see as extensive use for simple carbonyl reductions as borohydrides. Hydrosilane reducing agents broadly fall into one of two general categories: either a) they are easy to handle and require expensive and/or hazardous additives, or b) they are difficult and/or dangerous to handle. This work details the discovery of mild and functional group compatible conditions utilizing hydrosilatrane for the selective reduction of aryl aldehydes to benzylic alcohols without unwanted formation of ethers or deoxygenated products. This method offers significant advances in silane reductions as silatrane is an air- and moisture-stable yet relatively reactive reducing agent that can be used in benchtop open air reactions.
- Skrypai, Vladislav,Hurley, Joseph J. M.,Adler, Marc J.
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supporting information
p. 2207 - 2211
(2016/05/09)
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- Signal transduction and amplification through enzyme-triggered ligand release and accelerated catalysis
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Signal transduction and signal amplification are both important mechanisms used within biological signalling pathways. Inspired by this process, we have developed a signal amplification methodology that utilises the selectivity and high activity of enzymes in combination with the robustness and generality of an organometallic catalyst, achieving a hybrid biological and synthetic catalyst cascade. A proligand enzyme substrate was designed to selectively self-immolate in the presence of the enzyme to release a ligand that can bind to a metal pre-catalyst and accelerate the rate of a transfer hydrogenation reaction. Enzyme-triggered catalytic signal amplification was then applied to a range of catalyst substrates demonstrating that signal amplification and signal transduction can both be achieved through this methodology.
- Goggins, Sean,Marsh, Barrie J.,Lubben, Anneke T.,Frost, Christopher G.
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p. 4978 - 4985
(2015/07/27)
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- Multivalent Molecular Shuttles - Effect of Increasing the Number of Centers in Switchable Catalysts
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A family of three molecular shuttles based upon ammonium/triazolinium salt motifs with one, two, and three catalytic centers were prepared along with their corresponding non-interlocked threads. The switching process for all rotaxanes was tested through an in situ procedure in solution. Furthermore, their organocatalysis of two Michale-type reactions by iminium activation was tested to check whether the increase of the number of catalytic centers in the same shuttle is a decisive factor to improve their efficiencies compared with those of single-active-site organocatalytic shuttles under the same conditions.
- álvarez, Celedonio M.,Barbero, Héctor,Miguel, Daniel
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supporting information
p. 6631 - 6640
(2015/10/29)
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- Metal-free, visible-light photoredox catalysis: Transformation of arylmethyl bromides to alcohols and aldehydes
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A mild, simple, and controllable metal-free photocatalytic system for the transformation of arylmethyl bromides to corresponding alcohols and aldehydes in high yields with visible-light irradiation has been achieved. Eosin Y was found to be an efficient promoter for this oxidative dehalogenation reaction under photo irradiation conditions.
- Li, Jian,Wang, Hongni,Liu, Li,Sun, Jiangtao
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p. 49974 - 49978
(2014/12/10)
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- Fluorogenic aldehydes bearing arylethynyl groups: Turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO
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Fluorogenic aromatic aldehydes bearing arylethynyl groups were developed. They were used for monitoring the reaction progress of organocatalytic aldol reactions in DMSO through an increase in the fluorescence intensity based on the formation of the florescent aldol product. The ratios of the fluorescence intensities of the aldols to the aldehydes were more than 300. These results suggest that the fluorescence assay system using the aldehyde is useful for the rapid identification of superior aldol catalysts and reaction conditions.
- Mase, Nobuyuki,Ando, Taishi,Shibagaki, Fumiya,Sugita, Atsushi,Narumi, Tetsuo,Toda, Mitsuo,Watanabe, Naoharu,Tanaka, Fujie
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supporting information
p. 1946 - 1948
(2014/03/21)
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- Fluorogenic probes for chemical transformations: 9-anthracene derivatives for monitoring reaction progress by an increase in fluorescence
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The development of fluorogenic probes for chemical transformations bearing anthracene as a fluorescent core moiety is reported. Fluorogenic probes were designed by linking anthracene with functional groups used for reactions of interest. Each fluorogenic probe, possessing a reaction group such as aldehyde, α,β-unsaturated ketone, or imine at the 9-position of the anthracene, showed no or very low fluorescence. Reaction products of the probes, including aldol and addition products, were highly fluorescent. The products showed more than 1000-fold higher fluorescence than did the fluorogenic probes under the same conditions. The utility of the fluorogenic probes was demonstrated in monitoring the progress of a catalyzed aldol reaction.
- Mase, Nobuyuki,Takabe, Kunihiko,Tanaka, Fujie
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supporting information
p. 4306 - 4308
(2013/07/26)
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- Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes
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Novel 1,3-disulfonic acid imidazolium hydrogen sulfate, a halogen-free ionic liquid, is a recyclable and eco-benign catalyst for the trimethylsilyl protection of hydroxyl groups at room temperature under solvent free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-5 min). Deprotection of the resulting trimethylsilanes can also be achieved using the same catalyst in methanol. The catalyst was characterized by IR, 1H NMR, 13C NMR and MS studies. All the products were extensively characterized by IR, 1H NMR, MS, and elemental and melting point analyses. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered and reused for several times without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.
- Shirini, Farhad,Khaligh, Nader Ghaffari,Akbari-Dadamahaleh, Somayeh
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- Nanocrystalline TiO2-HClO4 as a new, efficient and recyclable catalyst for the chemoselective trimethylsilylation of alcohols, phenols and deprotection of silyl ethers
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TiO2-HClO4, as a new solid acid, was found to be an efficient catalyst for the chemoselective trimethylsilylation of alcohols and phenols. Deprotection of the resulting trimethylsilylethers was achieved using the same catalyst in methanol solvent. The synthesized catalyst was characterized by FT-IR, SEM, TEM, BET and XRD analyses. Our novel synthetic method has the advantages of high yields, short reaction times, low cost and recyclability of the catalyst, simplicity and easy work-up compared to the conventional methods reported in the literature.
- Shirini, Farhad,Atghia, Seyyed Vahid,Jirdehi, Mojtaba Ghazi
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- Magnesium-catalysed hydroboration of aldehydes and ketones
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The heteroleptic magnesium alkyl complex [CH{C(Me)NAr}2Mg nBu] (Ar = 2,6-iPr2C6H3) is reported as a highly efficient pre-catalyst for the hydroboration of aldehydes and ketones with pinacolborane. The Royal Society of Chemistry 2012.
- Arrowsmith, Merle,Hadlington, Terrance J.,Hill, Michael S.,Kociok-Koehn, Gabriele
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supporting information; experimental part
p. 4567 - 4569
(2012/06/05)
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- Rapid and efficient protection of alcohols and phenols, and deprotection of trimethylsilyl ethers catalyzed by a cerium-containing polyoxometalate
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Herein, we want to report a simple and convenient way for protection-deprotection of alcohols in the presence of ammonium decatungstocerate(IV) {(NH4)8[CeW10O 36]A·20H2O} as catalyst under ambient temperature in CH3CN. Using 0.002 mmol of the catalyst, various alcohols and phenols were transformed easily to the corresponding TMS ethers in excellent yields. In the second part, various TMS ethers were successfully converted to the parent hydroxyl compounds in the presence of the ammonium decatungstocerate(IV) catalyst.
- Yadollahi, Bahram,Mirkhani, Valiollah,Tangestaninejad, Shahram,Karimian, Davud
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experimental part
p. 83 - 86
(2012/06/18)
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- Synthesis and inclusion ability of anthracene appended β- cyclodextrins: Unexpected effect of triazole linker
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A new fluorescent β-cyclodextrin has been synthesized by coupling an anthracene moiety to the cyclic oligosaccharide via click chemistry. The influence of the triazole spacer was compared to the simple amino and amido linkers. While a sensing ability toward adamantan-1-ol was observed with the latter two spacers, the absence of inclusion capacity prevents the triazole modified cyclodextrin from showing any fluorescence variations. The difference in the binding behaviors studied by Isothermal Titration Calorimetry, UV-vis and fluorescence spectroscopies, was highlighted by the NOESY NMR spectra of the modified cyclodextrins: whereas a free cavity was observed for the amino and amido linkers, an important obstruction was obtained in the case of the triazole.
- Mallard, Isabelle,Landy, David,Bouchemal, Nadia,Fourmentin, Sophie
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experimental part
p. 35 - 42
(2011/02/25)
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- Diels-Alder reaction of 9-anthracenemethanol and dimethylacetylene- dicarboxylate; potential route for the synthesis of regiospecific products of 9-substituted anthracene with unsymmetrical acetylenes
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Diels-Alder reaction of 9-anthracenemethanol with dimethylacetylene- dicarboxylate gives rise to the formation of a lactone derivative by condensation of the alcoholic function of the 9-substituent with the nearby carboxylate group in the Diels-Alder adduct. Opening of the lactone derivative with an alcohol yields the desired Diels-Alder adduct. If the alcohol used for opening the lactone is different from the alcohol part of the dicarboxylate, the reaction gives the regiospecific adduct in which the alkoxy group (used for opening the lactone) is ortho to the 9-substituent.
- Singh, M. Dhaneshwar,Ningombam, Anjana
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experimental part
p. 77 - 83
(2010/04/26)
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- Catalytic hydrosilylation of carbonyl compounds with zinc(II) acetate: Asymmetric induction collaborated with N2S2 ligands
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Zinc acetate proved to be an efficient catalyst for hydrosilylation of ketones and aldehydes in the combination with (EtO)2MeSiH, and a good to excellent asymmetric induction was observed in the presence of chiral N 2S2 ligands. Georg Thieme Verlag Stuttgart.
- Inagaki, Tomohiko,Yamada, Yoko,Le, Thanh Phong,Furuta, Akihiro,Ito, Jun-Ichi,Nishiyama, Hisao
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experimental part
p. 253 - 256
(2009/05/30)
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- Rotaxanes of a macrocyclic ferrocenophane with dialkylammonium axle components
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Octaoxa[22]ferrocenophane, 1, was synthesized and employed as the macrocyclic component of [2]rotaxanes. [2]Pseudorotaxanes composed of macrocyclic molecule 1 and dialkylammonium derivatives with a terminal vinyl group undergo end-capping via cross-metathesis of the terminal group with bulky acrylates. The [2]rotaxanes of 1 with axle components having bulky terminal groups, such as 3,5-dimethylphenyl, 9-anthryl, and ferrocenyl groups, maintain an interlocked structure in CDCl3 solution, but they are gradually converted into a mixture of the individual components via dethreading of the end groups in polar solvents such as CD3CN and dmso-d6. The reaction rate varies depending on the end group and solvent. The cationic rotaxane with an anthryl end group of the axle component, [(1){AnCH 2NH2CH2C6H4-4-OCH 2CH2CHCHCOOC6H4-4-C(C 6H4-4-tBu)3}](BArF) (An = 9-anthryl, BArF = B{C6H3-3,5-(CF3) 2}4) shows weak emission upon excitation of the anthryl group (12b, λem = 419 nm, quantum yield, = 0.012). The quantum yield is lower than that of the neutral rotaxane 13b ( = 0.030) formed by N-acetylation of 12b and a physical mixture of the corresponding free axle molecule, AnCH2N(Ac)CH2C6H4-4- OCH2CH2CHCHCOOC6H4-4-C(C 6H4-4-tBu)3 (8), and 1 ( = 0.34). The efficiency of the quenching caused by the ferrocenylene group caused by energy transfer is affected significantly by the relative positions of the anthryl and ferrocenylene groups in the rotaxane. The rotaxane with axles having a secondary ammonium moiety has a redox potential E1/2 = -0.03-0.02 V (vs. Ag+/Ag), which is lower those of than compound 1 (E1/2 = -0.10 V) and the neutral [2]rotaxanes with the N-acetylated axle components (E1/2 = -0.11 and -0.22 V). The Royal Society of Chemistry 2009.
- Suzaki, Yuji,Chihara, Eriko,Takagi, Atsuko,Osakada, Kohtaro
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supporting information; experimental part
p. 9881 - 9891
(2010/03/04)
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- Amine-guanidine switch: A promising approach to improve DNA binding and antiproliferative activities
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A series of polyaromatic guanidino derivatives was synthesized and evaluated for growth inhibitory properties in several human carcinoma cell lines. The properties of these guanidino compounds were compared to those of their corresponding synthetic amino precursors. The size of the polyaromatic ring system as well as the length of the tether attached to the ring had a direct impact on the observed antiproliferative profiles, compound 14 having the broadest spectrum of activity. As both series intercalate DNA, guanidine derivatives showed a remarkable affinity for DNA and the guanidinium group appeared to be essential, yet not sufficient for caspase-3/7 activation. Compound 14 also showed significant in vivo activity against breast cancer cell xenografts in NOG/SCID mice. These results suggest that the electronic nature of chain tethering an intercalator not only influences the DNA-binding process but also controls the antitumoral activity of the whole compound.
- Ohara, Keiichiro,Smietana, Michael,Restouin, Audrey,Mollard, Séverine,Borg, Jean-Paul,Collette, Yves,Vasseur, Jean-Jacques
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p. 6465 - 6475
(2008/04/12)
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- Anthracene-9-methanol - A novel fluorescent phototrigger for biomolecular caging
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Photoexcitation of a solution of anthracene-9-methanol derived esters at ～386 nm in CH3CN/H2O (3:2 v/v) results in fluorescence emission in the 380-480 nm range, with quantum yields of fluorescence (Φf) in the 0.01-0.09 range and releases of the carboxylic acids in good chemical yields (43-100%), with quantum yields of photoreaction (ΦPR, i.e., the photodisappearance of the esters) in the 0.067-0.426 range.
- Singh, Anil K.,Khade, Prashant K.
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p. 5563 - 5566
(2007/10/03)
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- Reduction of aldehydes and oximes to their corresponding alcohols and amines by catalytic hydrogenation method
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The reduction of aldehydes such as 2-butyl-5-chloro-3H-imidazole-5- carbaldehyde and veratraldehyde, which are pharmaceutical key intermediates, have been reduced to alcohols by catalytic hydrogenation method in the presence of magnesium and also oximes are reduced to primary amines successively by magnesium/ammonium formate system, is a large scale feasible and cheaper method. The crystal structure of the product, (2-butyl-5-chloro-3H-imidazole-4-yl)- methanol 1 is reported.
- Basappa,Doreswamy,Mahendra,Mantelingu,Sridhar,Prasad, J. Shashidhara,Rangappa
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p. 148 - 151
(2007/10/03)
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- Efficient and simple NaBH4 reduction of esters at cationic micellar surface
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(Chemical Equation Presented) A simple, efficacious, and biocompatible methodology for reducing esters with sodium borohydride at an aqueous cationic micellar surface under ambient conditions has been developed. The present method holds promise for future use in selective functional group reduction and stereocontrolled alcohol synthesis.
- Das, Debapratim,Roy, Sangita,Das, Prasanta Kumar
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p. 4133 - 4136
(2007/10/03)
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- Intramolecular electrophilic aromatic substitution in gas-phase-protonated difunctional compounds containing one or two arylmethyl groups
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A variety of dibenzyl esters and ethers undergo a rearrangement process upon isobutane chemical ionization and collision-induced dissociation of their MH+ ions, whereby a new bond is formed between the two benzyl groups, giving rise to abundant [C14H13]+ (m/z 181) ions. This rearrangement has been explained as an intramolecular electrophilic substitution in the gas phase occurring in an ion-neutral complex formed by the cleavage of one of the benzyl-oxygen bonds. A similar highly efficient intramolecular electrophilic substitution takes place in di-α- and β-naphthylmethyl adipates affording m/z 281 [C22H17]+ ions, but not in the sterically hindered di-9-anthracylmethyl adipate. An analogous efficient rearrangement occurs in benzyl α- and β-naphthylmethylcyclohexane-1,4-dicarboxylates and in benzyl α- and β-phenylethylcyclohexane-1,4-dimethanol ethers. The analogous rearrangement is much less efficient in benzylallyl, benzylpropargyl and benzyl-9-anthracylmethyl derivatives, even less in benzylisopropyl and benzylacetyl analogs, and it is absent in benzyltetrahydropyranyl derivatives. The distinctive behavior of the protonated difunctional benzyl derivatives is interpreted in terms of the energy requirements of the O - R bond heterolysis of the protonated functionalities, the ability of the neutral R′ groups (non-dissociated from the oxygen atom) to play the role of the nucleophile in the intramolecular electrophilic substitution processes and the electrophilicity of the R+ ions. Copyright
- Edelson-Averbukh,Mandelbaum
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p. 1169 - 1177
(2007/10/03)
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- Ruthenium-catalysed transfer hydrogenation of aromatic aldehydes with dioxane under KOH: Assistance of Cannizzaro reaction
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Aromatic aldehydes are reduced to the corresponding alcohols in dioxane at 80°C in the presence of a catalytic amount of a ruthenium catalyst together with KOH in moderate to good yields.
- Kim, Bok Tae,Cho, Chan Sik,Kim, Tae-Jeong,Shim, Sang Chul
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p. 368 - 369
(2007/10/03)
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- Spin-on-glass anti-reflective coatings for photolithography
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Anti-reflective coating materials for deep ultraviolet photolithography include one or more organic dyes incorporated into spin-on-glass materials. Suitable dyes are strongly absorbing over wavelength ranges around wavelengths such as 248 nm and 193 nm that may be used in photolithography. A method of making dyed spin-on-glass materials includes combining one or more organic dyes with alkoxysilane reactants during synthesis of the spin-on-glass materials.
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