- PHOTOCHEMICAL VS. ELECTROCHEMICAL ELECTRON-TRANSFER REACTIONS. ONE-ELECTRON REDUCTION OF ARYL HALIDES BY PHOTOEXCITED ANION RADICALS.
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Electrochemical reduction of aryl halides generally leads to expulsion of halide ion.The product aryl radical is unavoidably further reduced.In contrast, reduction of aryl halides by photoexcited anion radicals may be stopped at the aryl radical stage owing to the bimolecular nature of electron-transfer reactions.We have tested this hypothesis by photoinducing electron-transfer from anthraquinone anion radical to several aryl halides.For each halide it was possible to trap the corresponding radical by anthracene forming substituted 9-phenylanthracenes.
- Nelleborg, Palle,Lund, Henning,Eriksen, Jens
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Read Online
- When Anthracene and Quinone Avoid Cycloaddition: Acid-Catalyzed Redox Neutral Functionalization of Anthracene to Aryl Ethers
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Benzoquinone and 9-phenylanthracene barely undergo anticipated cycloaddition under acid catalysis. Instead, 9-anthracenyl aryl ethers are obtained as unexpected products. Mechanistic studies indicate that the reaction likely undergoes an ionic mechanism between protonated anthracene species and nucleophilic oxygen of 1,4-benzoquinone or 1,4-hydroquinone. A variety of 9-anthracenyl aryl ethers are constructed with this method. Produced anthracenyl aryl ethers are potential scaffolds for new fluorescent molecules.
- Ding, Nan,Ding, Nan,Ding, Nan,Li, Zhi
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supporting information
p. 4276 - 4282
(2020/06/04)
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- Photoreaction of anthracenyl phosphine oxides: Usual reversible photo- and heat-induced emission switching, and unusual oxidative P&C bond cleavage
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Anthracenyl(diphenyl)phosphine oxide and dianthracenylphenylphosphine oxide as photoactive compounds have been synthesized. Anthracenyl group of these compounds indicate the multi-functional roles such as an emission component, a photodimerization component, and a leaving group. When the light irradiation was performed under an oxygen atmosphere, photo-oxidative P&C bond cleavage to leave the antharacenyl group was observed. Moreover, phosphonyl radical was produced and then P&P bond formation to form diphosphane was observed.
- Katagiri, Kosuke,Yamamoto, Yukina,Takahata, Yuui,Kishibe,Fujimoto
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supporting information
p. 2026 - 2029
(2019/07/03)
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- Acene-based transmitter molecules for photon upconversion
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Provided herein are transmitter ligands that improve photon upconversion of near infrared light (NIR) to visible light. The presently provided ligands are complexed to semiconductor nanocrystals and improve triplet energy transfer from semiconductor nanocrystal to annihilator in triplet-triplet annihilation. Suitable applications include bio-imaging.
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Paragraph 0151; 0152
(2018/10/04)
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- Semiconducting Material Comprising a Phosphine Oxide Matrix and Metal Salt
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The present invention is directed to a semiconducting material comprising: i) a compound according to formula (I) wherein R1, R2 and R3 are independently selected from C1-C30-alkyl, C3-C30 cycloalkyl, C2-C30-heteroalkyl, C6-C30-aryl, C2-C30-heteroaryl, C1-C30-alkoxy, C3-C30-cycloalkyloxy, C6-C30 aryloxy, and from structural unit having general formula E-A-, wherein—A is a C6-C30 phenylene spacer unit, and—E is an electron transporting unit that is selected from C10-C60 aryl and C6-C60 heteroaryl comprising up to 6 heteroatoms independently selected from O, S, P, Si and B and that comprises a conjugated system of at least 10 delocalized electrons, and—at least one group selected from R1, R2 and R3 has the general formula E-A-; and ii) at least one complex of a monovalent metal having formula (II) wherein—M+ is a positive metal ion bearing a single elementary charge, and each of A1, A2, A3 and A4 is independently selected from H, substituted or unsubstituted C6-C20 aryl and substituted or unsubstituted C2-C20 heteroaryl, wherein a heteroaryl ring of at least 5 ring-forming atoms of the substituted or unsubstituted C2-C20 heteroaryl comprises at least one hetero atom selected from O, S and N.
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- Aggregation-Induced Singlet Oxygen Generation: Functional Fluorophore and Anthrylphenylene Dyad Self-Assemblies
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The assembly of monomeric building blocks can manifest the display of new properties, including optical, mechanical, and electrochemical functionalities. In this study, we sought to develop a functional fluorophore self-assembly that can generate reactive oxygen species only when aggregated. With an anthrylphenylene (AP) group, negatively charged and neutral fluorescein units form non-fluorescent H-aggregates in aqueous solution because of the weak intermolecular interaction between the anthracene and fluorescein moieties. In stark contrast, a boron dipyrromethene (BODIPY) and AP dyad produces two-color-emissive aggregates through the formation of an intermolecular charge-transfer (CT) complex between the electron-rich anthracene and electron-deficient BODIPY moieties. Furthermore, to our surprise, the BODIPY and AP dyad aggregates generate singlet oxygen (1O2) and photocytotoxicity upon excitation, indicating that the BODIPY–anthracene CT state favors an intersystem crossing process. Based on X-ray crystallographic analysis, the lattice-like molecular packing between the BODIPY and AP moieties was determined to bring about the unprecedented aggregation-induced 1O2 generation (AISG).
- Kim, Sooyeon,Zhou, Yang,Tohnai, Norimitsu,Nakatsuji, Hirotaka,Matsusaki, Michiya,Fujitsuka, Mamoru,Miyata, Mikiji,Majima, Tetsuro
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supporting information
p. 636 - 645
(2018/01/26)
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- Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents
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A direct transformation of carboxylic acid esters into arenes with 1,5-bifunctional organomagnesium reagents is described. This efficient and practical method enables the one-step defunctionalization of various carboxylic acid esters to prepare benzene, anthracene, tetracene, and pentacene derivatives. A double nucleophilic addition of the 1,5-organodimagnesium reagent to the ester is followed by an immediate 1,4-elimination reaction that leads to the direct [5+1] formation of a new aromatic ring.
- Link, Achim,Fischer, Christian,Sparr, Christof
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supporting information
p. 12163 - 12166
(2015/10/12)
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- The unprecedented J-aggregate formation of rhodamine moieties induced by 9-phenylanthracenyl substitution
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We report a substitution of 9-phenylanthracenyl group into rhodamine derivatives that can induce the J-aggregate formation of rhodamine moieties in the aqueous solution upon the addition of a halide ion. From X-ray crystallographic analysis, the dramatic red-shift in the absorption band (i.e. app. 100 nm) originates from the cooperative slipped-stacking of rhodamine and anthracene molecules.
- Kim, Sooyeon,Fujitsuka, Mamoru,Tohnai, Norimitsu,Tachikawa, Takashi,Hisaki, Ichiro,Miyata, Mikiji,Majima, Tetsuro
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supporting information
p. 11580 - 11583
(2015/07/15)
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- Extended fluorochromism of anthracene trimers with a meta-substituted triphenylamine or triphenylphosphine core
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Combining meta-triphenylamine or triphenylphosphine with three anthracene fluorophores gives rise to fluorescent non-planar triskelions 1 and 2. The emissive properties of 1 are highly solvatochromic, yielding blue to pale green and even pale yellow fluor
- Li, Zhiou,Ishizuka, Hiromi,Sei, Yoshihisa,Akita, Munetaka,Yoshizawa, Michito
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supporting information; experimental part
p. 1789 - 1794
(2012/09/07)
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- Bipolar anthracene derivatives containing hole- and electron-transporting moieties for highly efficient blue electroluminescence devices
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A series of bipolar anthracene derivatives containing hole-transporting triphenylamine and electron-transporting benzimidazole moieties were synthesized and characterized. These compounds possess high thermal properties and quantum yield in toluene solution but their photoluminescence spectra are sensitive to the polarity of the solvent. Three types of devices were fabricated to investigate their electron-transporting and hole-transporting as well as light-emitting properties. The electroluminescence spectra for the three derivatives B1, B3 and B4 show that they emit blue light, while the B2-based devices produced white light at a low current density because of the electromer formation. Moreover, a single layer OLED device for B4 exhibited a current efficiency of 3.33 cd A-1 with a pure blue color of CIE (x,y) of (0.16, 0.16) at 20 mA cm-2 and a maximum brightness of 8472 cd m-2 at 8.7 V. The Royal Society of Chemistry 2011.
- Huang, Jinhai,Su, Jian-Hua,Li, Xin,Lam, Mei-Ki,Fung, Ka-Man,Fan, Hai-Hua,Cheah, Kok-Wai,Chen, Chin H.,Tian, He
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experimental part
p. 2957 - 2964
(2011/10/04)
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- Molecular engineering to improve the charge carrier balance in single-layer silole-based OLEDs
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We report a molecular engineering study on optical, structural and electrical properties of seven silole derivates aimed at enhancing the charge carrier balance in single-layer devices. By functionalizing two hole-transporting groups, dipyridylamine and anthracene, on the silole ring, we have investigated the influence of both substituents on the hole current. We have concluded that in contrast to dipyridylamine groups, anthracene groups decrease the charge carrier balance since the latter groups not only increase the hole current but also electron contribution. Mixing these hole-transporting groups and doubling their number lead to a novel silole becoming a very efficient emissive layer exhibiting threshold voltage below 3 V and luminous efficiency Le = 0.8 cd A-1 at 7 V. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2009.
- Aubouy, Laurent,Huby, Nolwenn,Hirsch, Lionel,Van Der Lee, Arie,Gerbier, Philippe
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scheme or table
p. 1290 - 1300
(2009/09/24)
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- Cyanine Borate Salts That Form Penetrated Ion Pairs in Benzene Solution: Synthesis, Properties, and Structure
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A series of cyanine borate salts were prepared and studied by laser spectroscopy, fluorescence spectroscopy, NMR spectral methods, and computer modeling.Analysis of the chemical, physical, and spectral properties of these salts shows that, in benzene solution, they form penetrated ion pairs.The center-to-center distance between the ions is less than the sum of the individual ionic radii.We call such structures penetrated ion pairs.Penetration affects the properties of the cyanine dyes in unique ways that are described.
- Murphy, Sean,Yang, Xiquiang,Schuster, Gary B.
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p. 2411 - 2422
(2007/10/02)
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- Dihydroazulene/Vinylheptafulvene Photochromism: Effect of ?-Arylenes on the Switching Behavior
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The reversible interconversion of dihydroazulene (DHA) and vinylheptafulvene (VHF) can be utilized to switch a number of physical properties.This communication reports on a fluorescent switch.By a multistep sequence involving an cycloaddition rout
- Spreitzer, Hubert,Daub, Joerg
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p. 1637 - 1642
(2007/10/02)
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