Dimethyldiphenyl Ether Research Articles

Red-Emitting Thermally Activated Delayed Fluorescence Polymers with Poly(fluorene-co-3,3′-dimethyl diphenyl ether) as the Backbone

A series of red-emitting thermally activated delayed fluorescence (TADF) polymers have been designed and synthesized based on poly(fluorene-co-3,3′-dimethyl diphenyl ether) (PFDMPE) as the backbone. Compared with polyfluorene (PF, 2.16 eV), the introduction of 3,3′-dimethyl diphenyl ether into the main chain of PFDMPE leads to the increased triplet energy of 2.58 eV, which is higher enough than the tethered red TADF guest (2.13 eV) to prevent the unwanted triplet energy back-transfer. Meanwhile, there is a good overlap between the absorption spectrum of the red guest and the photoluminescence (PL) spectrum of the polymeric host, ensuring the efficient energy transfer from host to guest. Consequently, the resultant polymers PFDMPE-R01 to PFDMPE-R10 in solid states show obvious red TADF properties with delayed fluorescence lifetimes of 126–191 μs and PL quantum yields of 0.18–0.55. Among them, PFDMPE-R05 obtains the best device performance, revealing a bright red electroluminescence peaked at 606 nm and a p...

Anti-HSV-1, antioxidant and antifouling phenolic compounds from the deep-sea-derived fungus Aspergillus versicolor SCSIO 41502

Chemical investigation of the deep-sea-derived fungus Aspergillus versicolor SCSIO 41502 resulted in the isolation of three new anthraquinones, aspergilols G-I (1–3), one new diphenyl ether, 4-carbglyceryl-3,3′-dihydroxy-5,5′-dimethyldiphenyl ether (4), and one new benzaldehyde derivative, 2,4-dihydroxy-6-(4-methoxy-2-oxopentyl)-3-methylbenzaldehyde (5), along with 23 known phenolic compounds (6–28). The structures of new compounds were elucidated by extensive spectroscopic analysis. The absolute configuration of 3 was established by CD spectrum and the modified Mosher method. Compounds 2, 3 and 9 had evident antiviral activity towards HSV-1 with EC50 values of 4.68, 6.25, and 3.12μM, respectively. Compounds 15, 18, 20 and 22–24 showed more potent antioxidant activity than l-ascorbic acid with IC50 values of 18.92–52.27μM towards DPPH radicals. Comparison of the structures and antioxidant activities of 1–28 suggests that the number of phenolic hydroxyl group that can freely rotate can significantly affect the antioxidant activity of phenolic compounds. In addition, 4, 22–24 and 27 had significant antifouling activity against Bugula neritina larval settlement with EC50 values of 1.28, 2.61, 5.48, 1.59, and 3.40μg/ml, respectively.

Pseudaboydins A and B: novel isobenzofuranone derivatives from marine fungus Pseudallescheria boydii associated with starfish Acanthaster planci.

Two novel isobenzofuranone derivatives, pseudaboydins A (1) and B (2), along with five known compounds, including (R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-5-hydroxybenzofuran (3), (R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-5-methoxybenzofuran (4), 3,3′-dihydroxy-5,5′-dimethyldiphenyl ether (5), 3-(3-methoxy-5-methylphenoxy)-5-methylphenol (6) and (−)-regiolone (7), were isolated from the culture broth of the marine fungus, Pseudallescheria boydii, associated with the starfish, Acanthaster planci. Their structures were elucidated primarily based on NMR and MS data. The absolute configurations of 1–4 were determined by CD spectroscopy and single-crystal X-ray diffraction studies. The cytotoxic and antibacterial activities of 1–4 were evaluated. Pseudaboydin A (1) showed moderate cytotoxic activity against human nasopharyngeal carcinoma cell line HONE1, human nasopharyngeal carcinoma cell line SUNE1 and human glandular lung cancer cell line GLC82 with IC50 values of 37.1, 46.5 and 87.2 μM, respectively.

Induced Production of Halogenated Diphenyl Ethers from the Marine‐Derived Fungus Penicillium chrysogenum

Manipulation of the fermentation of the marine-derived fungus Penicillium chrysogenum by addition of CaBr(2) resulted in induced production of bromodiphenyl ether analogs. Two new free-radical-scavenging polybrominated diphenyl ethers, 1 and 2, and three known diphenyl ethers, 3,3'-dihydroxy-5,5'-dimethyldiphenyl ether (3), and an inseparable mixture of violacerol-I (4) and violacerol-II (5) were isolated. The structures of the two new polybromodiphenyl ethers 1 and 2 were assigned by combined spectroscopic-data analysis, including deuterium-induced isotope effect. Compounds 1-3, and a mixture of 4 and 5 exhibited radical-scavenging activities against 1,1-diphenyl-2-picrylhydrazyl with IC(50) values of 18, 15, 42, and 6 μM, respectively. With the exception of 3, the compounds were, therefore, more active than the positive control, ascorbic acid (IC(50) 20 μM).

Reaction of 4,4′‐Dimethyldiphenyl Ether with Phosphorus Trichloride in the Presence of Anhydrous Aluminum Chloride.

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Reaction of 4,4′-dimethyldiphenyl ether with phosphorus trichloride in the presence of anhydrous aluminum chloride

The reaction of 4,4′-dimethyldiphenyl ether with phosphorus trichloride in the presence of anhydrous aluminum chloride was studied. This reaction affords 2,8-dimethyl-10H-10λ5-phenoxaphosphine 10-oxide as virtually the only product. In air, the latter in an alkaline solution is quantitatively transformed into 10-hydroxy-2,8-dimethyl-10H-10λ5-phenoxaphosphine 10-oxide.

Phenyl Ethers from Cultured Lichen Mycobionts of Graphis scripta var. serpentina and G. rikuzensis.

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Phenyl ethers from cultured lichen mycobionts of Graphis scripta var. serpentina and G. rikuzensis.

Spore-derived mycobionts of the lichen Graphis scripta var. serpentina and G. rikuzensis were cultivated on a malt-yeast extract medium supplemented with 10% sucrose and their metabolites were investigated. 3,3'-Dihydroxy-5,5'-dimethyldiphenyl ether was isolated from the cultures of the mycobionts of G. scripta var. serpentina, while a new phenyl ether, rikuzenol, along with two known diphenyl ethers, violaceol-I and violaceol-II, were isolated from those of G. rikuzensis. The structure of the new compound was determined by spectroscopic methods. Violaceol-I was chemically synthesized and interconversion between violaceol-I and violaceol-II was proven.

A New Azaphilone, Falconensin H, from Emericella falconensis.

A new azaphilone derivative, falconensin H (6), was isolated from mycelia of Emericella falconensis, together with previously reported falconensins A-D (1-4) and 3, 3'-dihydroxy-5, 5'-dimethyldiphenyl ether (5). The structure of 6 was elucidated by spectroscopic investigation and chemical correlations. Among the compounds isolated, only 5 showed antibacterial activity.

Mutants of Aspergillus nidulans blocked at an early stage of sporulation secrete an unusual metabolite.

Mutants of Aspergillus nidulans defective in conidiation (asexual sporulation) can be classified according to whether they are blocked before or after induction of conidiation. Mutants blocked before induction (preinduction mutants) appear to be unable to respond to the inducing stimulus and thus are defective in one of the earliest events in the sporulation process. Three preinduction mutants have been isolated and characterized. Each was found to exhibit the same pleiotropic phenotype: they also were defective in sexual sporulation and secreted a set of phenolic metabolites at a level much higher than did wild type or mutants blocked at later stages of conidiation. One of the metabolites has been identified as the antibiotic diorcinal (3,3'-dihydroxy-5,5'-dimethyldiphenyl ether) which is known to be involved in the synthesis of certain farnesyl phenols of unknown function. These results suggest that preinduction mutants are blocked in a phenolic metabolic pathway, one or more product of which participates in the initiation of sporulation.

Metabolic products of microorganisms. 196 The structure of ethericin B, a new diphenylether antibiotic.

Ethericin B(Ia) was isolated together with ethericin A1) from fermentations of Aspergillus funiculosus Tü 680. The structure of ethericin B was established as 4-carbethoxy-5,5'-dihydro-xy-3,3'-dimethyl-diphenyl ether by chemical degradation, mass spectrometry, 1H-NMR and comparison with synthetic 4-carbethoxy-5,5'-dimethoxy-3,3'-dimethyl-diphenyl ether.

The biosynthesis of phenols—XVII : Some phenolic metabolites of mutant strains of Aspergillus regulosus

Three metabolites which were isolated from different mutant strains of Aspergillus rugulosus have been identified as 2,4-dihydroxy-6-methylbenzaldehyde (III), 2,4-dihydroxy-6-(hydroxymethyl)-benzaldehyde (IV), and 3,3′-dihydroxy-5,5′-dimethyldiphenyl ether (V).

Synthetical Applications of Activated Metal Catalysts. XVII. The Hydrogenolysis of Aromatic Ethers by Raney Nickel

W7 Raney nickel reacts with diphenyl ether at atmospheric pressure to give benzene and cyclohexanol. Traces of phenol are also formed. Less cyclohexanol and more phenol are produced when this reaction is carried out either at room temperature or with a degassed Raney nickel catalyst. W7 Raney nickel has also been reacted with 4,4'-dimethyl diphenyl ether (to give toluene and trans-4-methyl-cyclohexanol), with 4,4'-dicarboxydiphenyl ether (to give benzoic acid and p-hydroxy-benzoic acid), with anisole (to give benzene and methanol), with dibenzofuran (to give trans-2-phenylcyolohexanol), and with cyclohexyl phenyl ether (to give benzene and cyclohexanol). Dicyclohexyl ether is not affected by W7 Raney nickel. These results are discussed in terms of a mechanism which involves the following steps (i) adsorption of the ether on the catalyst via the oxygen atom; (ii) fission of one of the carbon-oxygen bonds to give the more-stable hydrocarbon anion and phenol (or alcohol for an alkyl aryl ether) ; and (iii) hydrogenation of the phenol to give a cyclohexanol. The effect of variation of the structure of the ether on each of these steps is discussed. In agreement with this mechanism, an excess of W7 Raney nickel reduces at atmospheric pressure phenol and p-cresol (as the anions) to give cyclohexanol and trans-4-methylcyclohexanol respectively, while p-hydroxybenzoic acid and benzoic acid are largely recovered. cis-4-Methylcyclohexanol is not epimerized by W7 Raney nickel.

2,2´,3´-Trimethoxy-4, 5´-dimethyldiphenyl Etherの液体アンモニア中金属ナトリウムによる開裂反応

2,2´,3´-Trimethoxy-4, 5´-dimethyldiphenyl Etherの液体アンモニア中金属ナトリウムによる開裂反応