- A Suzuki Approach to Quinone-Based Diarylethene Photochromes
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Diarylethene photochromes show promise for use in advanced organic electronic and photonic materials with burgeoning considerations for biological applications; however, these compounds typically require UV light for photoswitching in at least one direction, thus limiting their appeal. We here introduce a naphthoquinone-based diarylethene that switches between open and closed forms with visible light. The synthesis of this quinone diarylethene relies on Suzuki methodology, allowing for the inclusion of functional groups not otherwise accessible with current synthetic routes.
- Carter, Dorothy A.,Mitchell, Travis B.,Myers, Shea D.,Novak, Frank A.,Patel, Dinesh G.
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- Electrochemical synthesis of quinones and other derivatives in biphasic medium
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Electrochemical synthesis of quinones has been attempted from phenols, 1,4-dihydroxybenzenes, 1,4-dihydroxynaphthalenes and related compounds using biphasic media. Excellent yields of quinones (98%) or brominated diols have been achieved with good current efficiency. Reuse of the electrolyte without any modification and quantitative conversion of substrate with theoretical amount of current are the advantages of this method.
- Shanmugam,Kulangiappar,Ramaprakash,Vasudevan,Senthil Kumar,Velayutham,Raju
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p. 2294 - 2297
(2017/05/19)
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- Artificial photosynthesis of methanol from carbon dioxide and water via a Nile red-embedded TiO2 photocathode
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The conversion of carbon dioxide into useful chemicals is a prospective strategy for alleviating the greenhouse effect and the depletion of energy. Herein, we report an artificial photosynthetic system composed of a photoanode and a photocathode comprised of NRx@TiO2 functionalized with Nile red via covalent linkage or Pd/NRx@TiO2 with additional palladium nanoparticles. The new Nile red derivatives and organic-inorganic composite electrodes were steadily prepared and well characterized using NMR, HRMS, UV-vis, FTIR, TEM, XPS, XRD and SEM. Methanol and oxygen were the products that could be detected in the liquid and gas phase. The main active species in this artificial photosynthesis system were proven using EPR spectroscopy to be hydroxy radicals releasing O2 gas via H2O2. Moreover, the carbon source of methanol was validated using a 13CO2 labeling experiment; 18O2 was determined to come from H2O using GC-MS. The optimal photoelectrocatalytic CO2 reduction was carried out using Pd/NR2@TiO2 as the working electrode yielding methanol at a rate of 106 μM h?1 cm?2 with high light quantum efficiency (Φcell = 0.95).
- Jia, Yongjian,Xu, Yanjie,Nie, Rong,Chen, Fengjuan,Zhu, Zhenping,Wang, Jianguo,Jing, Huanwang
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supporting information
p. 5495 - 5501
(2017/03/22)
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- Vicinal acetylenic derivatives of 2-amino-1,4-naphthoquinone as key precursors of heterocyclic quinones
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The Pd-catalyzed reaction between 3-acetylamino-2-bromo-1,4-naphthoquinones and CuI acetylides prepared in situ gave 3-acetylamino-2-alkynyl-1, 4-naphthoquinones, which were transformed into benz[f]indole-4,9-dione and benzo[g]quinoline-5,10-dione derivatives.
- Shvartsberg,Kolodina,Lebedeva,Fedenok
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p. 582 - 588
(2013/05/09)
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- Synthesis of benz[f]indole-4,9-diones via acetylenic derivatives of 1,4-naphthoquinone
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A synthetic route to benz[f]indole-4,9-diones from 1,4-naphthoquinone is described. Effective methods for cross-coupling of 3-acetylamino-2-bromo-1,4-naphthoquinone with terminal acetylenes and cyclization of the resulting 3-acetylamino-2-alkynyl-1,4-naphthoquinones are developed.
- Shvartsberg, Mark S.,Kolodina, Ekaterina A.,Lebedeva, Nadezhda I.,Fedenok, Lidiya G.
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scheme or table
p. 6769 - 6771
(2010/04/27)
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- Antiviral agents. I. Synthesis and antiviral evaluation of trimeric naphthoquinone analogues of conocurvone
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Conocurvone, a novel natural product isolated from the endemic Australian shrub Conosperum sp. (Proteaceae), exhibits anti-HIV activity but is a highly lipophilic compound, which suggests that there may be problems with its aqueous solubility and bioavailability. A general and convenient synthesis of trimeric naphthoquinones using the condensation of 2-hydroxynaphthoquinones and 2,3-dihaloquinones is described. The application of this method to the synthesis of a series of simpler and less lipophilic trimeric naphthoquinone simple analogues of conocurvone is also reported together with their anti-HIV activity. CSIRO 2008.
- Crosby, Ian T.,Rose, Mark L.,Collis, Maree P.,De Bruyn, Paula J.,Keep, Philip L. C.,Robertson, Alan D.
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p. 768 - 784
(2008/12/22)
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- Synthesis of Polyhalogenated 2-Cyclohexane-1,4-dione Derivatives Containing Hydrogen at the sp3-Carbon Atoms from N-Arylsulfonyl-p-quinonimines and N,N'-Bis(arylsulfonyl)-p-quinonediimines
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Chlorination and bromination of N-arylsulfonyl-1,4-benzo(naphtho)quinonimines, N,N'-bis(arylsulfonyl)-1,4-benzoquinonediimines, N-arylsulfonyl-4-aminophenols, and N-arylsulfonyl-4-aminonaphthols gave a number of stable polyhalogenated structures containing hydrogen at the sp3-hybridized carbon atoms. The chlorination and bromination schemes of N-arylsulfonyl-p-quinonimines are discussed.
- Avdeenko, A. P.,Zhukova, S. A.
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p. 388 - 396
(2007/10/03)
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- CONDENSATION INDOLE/NAPHTHOQUINONE. SYNTHESE D'UNE NOUVELLE SERIE D'INDOLYL-1,4-NAPHTHOQUINONES
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Addition of an indole, which does not have a group at the 3-position, to 1,4-naphthoquinone leads to the expected 2-(3-indolyl)-1,4-naphthoquinone.When the 1,4-naphthoquinone is substituted at the 2-position by an alkyl or aryl group, the 2-substituted 3-(3-indolyl)-1,4-naphthoquinone is easily formed.However, when the 2-substituent of the quinone is functional (OH, OMe, Cl, Br, NC5H10, S-C6H5), in addition to the new series of expected indolylnaphthoquinones, several by-products resulting from elimination of the 2-substituted and/or further reaction of these compounds are formed.The outcome at the reaction appears to be very sensitive to the experimental conditions.
- Henrion, Jean-Christophe,Jacquet, Bernard,Hocquaux, Michel,Lion, Claude
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p. 163 - 168
(2007/10/02)
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- Solid state redox chemistry of hydroquinones and quinones
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Solid state ceric ammonium nitrate (CAN) oxidation of hydroquinones to the corresponding quinones, gives best results when operating with ultrasonic irradiation. Nitrogen dioxide plays a key role in these 'solid-solid' oxidations. The oxidation of hydroquinones to quinones can also be achieved in a unique 'solid-solid-solid' reaction, i.e., by using a limited amount of CAN in the presence of a full equivalent of a solid cooxidant such as KBrO3. Reduction of quinones with sodium dithionite in the solid state gives rise to the corresponding highly colored quinhydrones and, eventually, to hydroquinones.
- Morey,Saa
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p. 105 - 112
(2007/10/02)
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- BROMINATION OF 4-ARENESULFONAMIDOPHENOLS (OR 1-NAPHTHOLS) AND N-ARYLSULFONYL-1,4-BENZO(NAPHTHO)QUINON-4-IMINES
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2,3,6-Tribromo-N-phenylsulfonyl-1,4-benzoquinon-4-imines are formed on bromination of 4-arenesulfonamidophenols and N-aryl-sulfonyl-1,4-benzoquinon-4-imines but 2-bromo-N-arylsulfonyl-1,4-naphthoquinon-4-imines are formed from 4-arenesulfonamido-1-naphthols and N-arylsulfonyl-1,4-naphthoquinon-4-imines.
- Avdeenko, A. P.,Velichko, N. V.
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p. 1687 - 1692
(2007/10/02)
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- A New Route to Naphthofuran-4,9-diones from Thio-substituted 1,4-Naphthoquinones
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Reaction of 2-phenylthio- or 2-ethylthio-1,4-naphthoquinones (1) and (2) with lithium enolates or pyridinium ylides was found to give alkylated 1,4-naphthoquionones (3)-(6) in high yields.Alkylated 1,4-naphthoquinones (5) and (6) were then effectively cyclized to 2-substituted naphthofuran-4,9-diones (8) by action of bromine in acetic acid.
- Kang, Wen-Bing,Sekiya, Takashi,Toru, Takeshi,Ueno, Yoshio
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p. 441 - 445
(2007/10/02)
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