- Deep-blue light-emitting polyfluorenes with asymmetrical naphthylthio-fluorene as Chromophores
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A novel blue polycyclic aromatic compound 2,8-dibromo-14,14-dioctyl-14H-benzo[b]benzo [5,6] fluoreno[1,2-d]thiophene 9,9-dioxide (Br2NFSO) is designed and synthesized through multistep synthesis, and its structure is confirmed by nuclear magnetic resonance. Based on synthesized polycyclic aromatic compound Br2NFSO, a series of twisted blue light-emitting polyfluorenes derivatives (PNFSOs) are prepared by one-pot Suzuki polycondensation. Based on the twisted polymer molecular structure resulted from the asymmetric links of 14,14-dioctyl-14H-benzo[b]benzo[5,6]fluoreno[1,2-d]thiophene 9,9-dioxide (NFSO) unit in copolymers and better electron transport ability of NFSO than those of the electron-deficient dibenzothiophene-S,S-dioxide counterpart, the resulting polymers exhibit excellent electroluminescent spectra stability in the current densities from 100 to 800 mA cm?2, and show blue-shifted and narrowed electroluminescent spectra with the Commission Internationale de L′Eclairage (CIE) of (0.16, 0.07) for PNFSO5, compared to poly(9,9-dioctylfluorene) (PFO) with the CIE of (0.18, 0.18). Moreover, the superior device performance is achieved based on PNFSO5 with the maximum luminous efficiency (LEmax) of 1.96 cd A?1, compared with the LEmax of 0.49 cd A?1 for PFO. The results indicate that the twisted polycyclic aromatic structure design strategy has a great potential to tuning blue emission spectrum and improving EL efficiency of blue light-emitting polyfluorenes.
- Hu, Liwen,Wu, Zhonglian,Wang, Xiaojun,Ma, Yawei,Guo, Ting,Ying, Lei,Peng, Junbiao,Cao, Yong
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Read Online
- Annelated Pyridine Bases for the Selective Acylation of 1,2-Diols
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A set of 24 annelated derivatives of 4-diaminopyridine (DMAP) has been synthesized and tested with respect to its catalytic potential in the regioselective acylation of 1,2-diol substrates. The Lewis basicities of the catalysts as quantified through quantum chemical calculations vary due to inductive substituent effects and intramolecular stacking interactions between side chain π-systems and the pyridinium core ring system. The primary over secondary hydroxyl group selectivities in catalytic acylations of 1,2-diol substrates depend on the size and the steric demand of the Lewis base and the anhydride reagent.
- Mayr, Stefanie,Zipse, Hendrik
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supporting information
(2022/03/08)
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- Efficient polyfluorene derivatives for blue light-emitting diodes enabled by tuning conjugation length of bulky chromophores
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In this work, a series of blue chromophores containing PAH core with different conjugation lengths and end-capped with diphenylamine were developed and introduced into PPF derivatives. Since the blue chromophores can enhance the thermal stability and suppress the interchain interactions efficiently, all copolymers present outstanding thermal decomposition temperatures up to 425 °C, high photoluminescence quantum yields (PLQYs) up to 48% and smooth surface morphology. Furthermore, the corresponding single-layer blue polymer light-emitting devices (PLEDs) based on these blue copolymers show good blue light emission peaking at 456–468 nm, and excellent stability of electroluminescence (EL) spectra. In particular, the best PLED with a maximum luminance of 8938 cd m?2, a maximum luminous efficiency (LEmax) of 3.73 cd A?1, Commission International de L'Eclairage (CIE) coordinates of (0.14, 0.16) is achieved based on PPF-F. These results demonstrate that tuning the conjugation length of the bulky chromophores in blue light-emitting polymers is a novel and effective molecular design strategy toward highly stable and efficient blue polymer light-emitting diodes.
- Guo, Feng,Hu, Liwen,Xiao, Biao,Yang, Renqiang,Ying, Lei,Zhang, Mingrui,Zhao, Sen
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- AROMATIC DIAMINE DERIVATIVE
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PROBLEM TO BE SOLVED: To provide an aromatic diamine derivative that makes it possible to prepare a blue organic electroluminescent element having high luminous efficiency and sufficient service life. SOLUTION: An aromatic diamine derivative is represente
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Paragraph 0207-0209
(2021/09/03)
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- Synthesis and photophysical properties of isocoumarin-based D-π-A systems
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We prepared a small library of polarity-sensitive fluorescent dyes characterized by an isocoumarin core properly functionalized with a conjugated push-pull system. The key step of the synthesis is based on a regio-selective silver(I)/p-TSA co-catalyzed cyclization of 2-alkynylbenzoates recently optimized in our laboratory. The photophysical properties of isocoumarin-based D-π-A systems have been investigated and a rationale was proposed based on their dipole moments and Hammett constants of the ED and EW groups involved.
- Pirovano, Valentina,Marchetti, Marialaura,Carbonaro, Jessica,Brambilla, Elisa,Rossi, Elisabetta,Ronda, Luca,Abbiati, Giorgio
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- Small molecule light-emitting material based on naphthothiodibenzofuran unit, preparation method and applications thereof
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The invention discloses a small molecule light-emitting material based on a naphthothiodibenzofuran unit, a preparation method and applications thereof, wherein the naphthothiodibenzofuran unit is beneficial to improving the electron affinity and promoting the injection and transmission of electrons, and has high fluorescence efficiency and high chemical stability. According to the invention, thesmall molecule light-emitting material based on the naphthothiodibenzofuran unit is obtained through a Suzuki or C-N coupling reaction, and has high thermal stability, good film-forming property and good dissolvability; and after the small molecule light-emitting material based on the naphthothiodibenzofuran unit is dissolved by adopting a common organic solvent, and the light emitting layer of alight-emitting diode is prepared through spin coating, vacuum evaporation, ink-jet printing or printing film formation.
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Paragraph 0031; 0037; 0038
(2020/03/06)
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- Red or near-infrared light operating negative photochromism of a binaphthyl-bridged imidazole dimer
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The development of red or near-infrared light (NIR) switchable photochromic molecules is required for an efficient utilization of sunlight and regulation of biological activities. While the photosensitization of photochromic molecules to red or NIR light has been achieved by a two-photon absorption process, the development of a molecule itself having sensitivity to red or NIR light has been now a challenging study. Herein, we developed an efficient molecular design for realizing red or NIR-light-responsive negative photochromism based on binaphthyl-bridged imidazole dimers. The introduction of electron-donating substituents shows the red shift of the absorption band at the visible-light region because of the contribution of a charge-transfer transition. Especially, the introduction of a di(4-methoxyphenyl)amino group (TPAOMe) and a perylenyl group largely shifts the absorption edge of the stable colored form to 900 nm. In addition, because the absorption band of one of the derivatives substituted with TPAOMe covers the whole visible-light region, the colored form shows a neutral gray color. Upon red (660 nm) or NIR-light (790 nm) irradiation, we observed the negative photochromic reaction from the stable colored form to the metastable colorless form. Therefore, the substituted binaphthyl-bridged imidazole dimers constitute the attractive photoswitches within a biological window.
- Kometani, Aya,Inagaki, Yuki,Mutoh, Katsuya,Abe, Jiro
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p. 7995 - 8005
(2020/05/27)
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- p-TSA-Based DESs as “Active Green Solvents” for Microwave Enhanced Cyclization of 2-Alkynyl-(hetero)-arylcarboxylates: an Alternative Access to 6-Substituted 3,4-Fused 2-Pyranones
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In this paper, we describe the use of p-TSA based Deep Eutectic Solvents (DESs) as alternative environmental-friendly “active” solvents for the microwave-mediated synthesis of 6-substituted 3,4-fused 2-pyranones, and in particular isocoumarins, starting from 2-alkynyl-(hetero)arylcarboxylates. When the alkyne terminus bears a neutral or an electron-donating group (EDG), the reactions are fast, clean and highly regioselective, to give the 6-endo-dig cyclization products in good to excellent yields. For substrates bearing an electron-withdrawing group (EWG) on the alkyne end, the regioselectivity can be tuned by adding a small amount of silver(I) triflate as co-catalyst. DES was demonstrated to be reusable without loss of efficiency in terms of reaction yields. Based on experimental evidence and previous findings, two competitive mechanisms working simultaneously are proposed to explain the outcomes and the regioselectivity issues.
- Curti, Fabiola,Tiecco, Matteo,Pirovano, Valentina,Germani, Raimondo,Caselli, Alessandro,Rossi, Elisabetta,Abbiati, Giorgio
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p. 1904 - 1914
(2019/02/26)
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- 9-Benzofiurene-terminated electroluminescence material as well as preparation method and application thereof
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The invention discloses a 9-benzofiurene-terminated electroluminescence material as well as a preparation method and application thereof. The electroluminescence material adopts a five-membered ring structure as a core, respectively adopts C-C or C-N to b
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Paragraph 0062-0064
(2018/05/16)
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- Exploration of Biaryl Carboxylic Acids as Proton Shuttles for the Selective Functionalization of Indole C-H Bonds
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A survey of diversely substituted 2-arylbenzoic acids were synthesized and tested for use as proton shuttle in the direct arylation of indoles with bromobenzenes. It was found that 3-ethoxy-2-phenylbenzoic acid gives superior yield and selectivity for this class of substrates.
- Pi, Jing-Jing,Lu, Xiao-Yu,Liu, Jing-Hui,Lu, Xi,Xiao, Bin,Fu, Yao,Guimond, Nicolas
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p. 5791 - 5800
(2018/05/14)
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- Bipolar micromolecular luminescent material taking naphthalene diindenofluorene cell as core, and preparation method and application of bipolar micromolecular luminescent material
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The invention discloses a bipolar micromolecular luminescent material taking a naphthalene diindenofluorene cell as a core, and a preparation method and application of the bipolar micromolecular luminescent material. The naphthalene diindenofluorene cell
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Paragraph 0041; 0042; 0043; 0044
(2017/07/19)
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- Bipolar small molecular light-emitting material based on naphthothiodibenzofuran unit as well as preparation method and application of bipolar small molecular light-emitting material
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The invention discloses a bipolar small molecular light-emitting material based on a naphthothiodibenzofuran unit as well as a preparation method and application of the bipolar small molecular light-emitting material. The preparation method provided by th
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Paragraph 0033; 0034; 0035; 0036
(2017/07/19)
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- Bipolar blue-light micro-molecular luminescent material based on naphtho-8-S,S-dioxydibenzothiophene unit, and preparation method and application thereof
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The invention discloses a bipolar blue-light micro-molecular luminescent material based on a naphtho-8-S,S-dioxydibenzothiophene unit, and a preparation method and application thereof. According to the invention, the naphtho-8-S,S-dioxydibenzothiophene un
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Paragraph 0034; 0035; 0036; 0037
(2017/09/13)
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- Bipolar micro-molecular luminescent material based on naphtho-2,7-S,S-dioxydibenzothiophene unit, and preparation method and application thereof
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The invention discloses a bipolar micro-molecular luminescent material based on a naphtho-2,7-S,S-dioxydibenzothiophene unit, and a preparation method and application thereof. According to the invention, the naphtho-2,7-S,S-dioxydibenzothiophene unit is u
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Paragraph 0032; 0033; 0034; 0035
(2017/09/13)
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- Organic photovoltaic cell micromolecule receptor material using naphtho-indenofluorene unit as core, and preparation method and application thereof
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The invention discloses an organic photovoltaic cell micromolecule receptor material using a naphtho-indenofluorene unit as a core and a preparation method and the application thereof. The preparation method is characterized in that the polar substituent group containing naphtho-indenofluorene unit is used as the core; electron withdrawing units are sequentially connected to two sides of the naphtho-indenofluorene unit through coupling reaction to obtain the organic photovoltaic cell micromolecule receptor material using the naphtho-indenofluorene unit as the core; the organic photovoltaic cell micromolecule receptor material using the naphtho-indenofluorene unit as the core and a donor material are dissolved into an organic solvent; the surface of an ITO/ PEDOT: PSS is spirally coated with the mixture to form a film; then a residual organic solvent is removed by evaporating to dryness, therefore, an active layer of an organic photovoltaic cell can be obtained. The organic photovoltaic cell micromolecule receptor material using the naphtho-indenofluorene unit as the core has the characteristics of simplicity in structure, and easiness in process.
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Paragraph 0051; 0052; 0053; 0054; 0055
(2018/01/11)
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- Synthesis method of axially chiral dinaphthalene ligand precursor (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid
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The invention relates to the technical field of bromination, hydrolysis, oxidation and coupling reaction in organic synthesis, particularly a synthesis method of an axially chiral dinaphthalene ligand precursor (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid. The method comprises the following steps: synthesizing a compound 1-bromo-2-methylnaphthalene from an initial raw material 2-bromomethylnaphthalene, carrying out bromination, hydrolysis and oxidation on the 1-bromo-2-methylnaphthalene to obtain 1-bromo-2-naphthoic acid, generating an ester under the actions of methanol and thionyl chloride, protecting the carboxyl group, carrying out Ullmann reaction under the action of copper powder to perform coupling, carrying out hydrolysis to obtain 2,2'-dinaphthyl-1,1'-dicarboxylic acid, and finally, resolving to obtain the (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid. The method is simple to operate, and has the advantages of higher yield and favorable economical efficiency.
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- Palladium NNC Pincer Complex as an Efficient Catalyst for the Cycloisomerization of Alkynoic Acids
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A two-step (nucleophilic substitution/palladation by oxidative addition) sequence provides a high-yielding access to a non-symmetrical palladium NNC pincer complex. A number of terminal and internal alkynoic acids with different substitution patterns at the α- and β-positions are regio- and diastereoselectively cycloisomerized to the corresponding exocyclic enol lactones in the presence of exceedingly low amounts of the latter palladium complex, so that unprecedented turnover numbers and frequencies ranging from 1,000,000 to 700,000 and from 41,667 to 9722 h?1, respectively, are achieved. The optimized protocol, based on the use of a catalytic amount of triethylamine as base, allows an easy real-time monitoring of the reaction by NMR spectroscopy. Several pieces of evidence in favor of the direct participation of the above pincer complex as the catalyst of the reaction have been gathered from kinetic and poisoning experiments. (Figure presented.).
- Conde, Nerea,SanMartin, Raul,Herrero, María Teresa,Domínguez, Esther
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supporting information
p. 3283 - 3292
(2016/10/21)
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- Asymmetric Suzuki-Miyaura cross-coupling of 1-bromo-2-naphthoates using the helically chiral polymer ligand PQXphos
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A single-handed helical polymer ligand PQXphos afforded axially chiral biaryl esters with high enantioselectivities in asymmetric Suzuki-Miyaura cross-coupling. The use of naphthyl bromide bearing a 2,4-dimethyl-3-pentyl ester resulted in both high yields and high enantioselectivities. Either enantiomer could be synthesized selectively by using a single PQXphos through a solvent-dependent switch of the helical chirality. This journal is
- Akai, Yuto,Konnert, Laure,Yamamoto, Takeshi,Suginome, Michinori
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supporting information
p. 7211 - 7214
(2015/04/27)
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- Selenium-catalyzed C(sp3)-H acyloxylation: Application in the expedient synthesis of isobenzofuranones
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Oxidative Se-catalyzed C(sp3)-H bond acyloxylation has been used to construct a diverse array of isobenzofuranones from simple ortho-allyl benzoic acid derivatives. The synthetic procedure employs mild reaction conditions and gives high chemoselectivity enabled by an inexpensive organodiselane catalyst. The presented approach offers a new synthetic pathway toward the core structures of phthalide natural products.
- Kr?tzschmar, Felix,Kassel, Martin,Delony, Daniel,Breder, Alexander
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supporting information
p. 7030 - 7034
(2015/05/05)
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- Design and synthesis of new stable fluorenyl-based radicals
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Organic neutral radicals have long fascinated chemists with a fundamental understanding of structure-reactivity relationships in organic reactions and with applications as new functional materials. However, the elusive nature of these radicals makes the synthesis, isolation, and characterization very challenging. In this work, the synthesis of three long-lived, fluorenyl-based radicals are reported. The geometry and electronic structures of these radicals were systematically investigated with a combination of various experimental methods, besides density functional theory (DFT) calculations, which include X-ray crystallographic analysis, electron spin resonance (ESR), electron nuclear double resonance (ENDOR), cyclic voltammetry, and UV-vis-NIR measurements. Their half-life periods (τ1/2) in air-saturated solution under ambient conditions were also determined. Surprisingly, all three radicals showed remarkable stabilities: τ1/2 = 7, 3.5, and 43 days.
- Tian, Yi,Uchida, Kazuyuki,Kurata, Hiroyuki,Hirao, Yasukazu,Nishiuchi, Tomohiko,Kubo, Takashi
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p. 12784 - 12793
(2015/02/19)
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- Supramolecular control of selectivity in hydroformylation of vinyl arenes: Easy access to valuable β-aldehyde intermediates
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Go against the flow! A rationally designed regioselective hydroformylation catalyst, [Rh/L], in which noncovalent ligand-substrate interactions allow the unprecedented reversal of selectivity from the typical α-aldehyde to the otherwise unfavored product β-aldehyde, is reported. This catalytic system opens up novel and sustainable synthetic pathways to important intermediates for the fine-chemicals industry.
- Dydio, Pawel,Reek, Joost N. H.
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supporting information
p. 3878 - 3882
(2013/05/09)
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- A suite of activity-based probes for human cytochrome P450 enzymes
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Cytochrome P450 (P450) enzymes regulate a variety of endogenous signaling molecules and play central roles in the metabolism of xenobiotics and drugs. We recently showed that an aryl alkyne serves as an effective activity-based probe for profiling mouse liver microsomal P450s in vitro and in vivo. However, individual P450s display distinct substrate and inhibitor specificities, indicating that multiple probe structures may be required to achieve comprehensive coverage of this large and diverse enzyme family. Here, we have synthesized a suite of P450-directed, activity-based protein profiling (ABPP) probes that contain: (1) varied chemical architectures validated as mechanism-based inhibitors of the P450 enzyme family, and (2) terminal alkyne groups for click chemistry conjugation of reporter tags. This set of probes was screened against a wide cross-section of human P450s, leading to the discovery of an optimal set of probes that provide broad coverage of this enzyme family. We used these probes to profile the effects on P450 activity of aromatase inhibitors in current clinical use for the treatment of breast cancer. We describe the surprising discovery that one of these aromatase inhibitors, anastrozole, significantly increases probe-labeling of P450 1A2, indicative of a heterotypic cooperativity effect on a central P450 isozyme involved in metabolizing numerous drugs and xenobiotics. The results presented herein greatly expand the suite of ABPP probes for profiling P450s and illuminate new applications for these tools to understand P450-drug interactions.
- Wright, Aaron T.,Song, Joongyu D.,Cravatt, Benjamin F.
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scheme or table
p. 10692 - 10700
(2009/12/08)
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- NEW CXCR2 INHIBITORS
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The invention relates to compounds of the formula (I), in which R1, R2, X, A, B, Z and Y1 to Y4 have the meanings indicated in the claims, and/or a pharmaceutically acceptable salt and/or a prodrug thereof. Because of their properties as inhibitors of chemokine receptors, especially as CXCR2 inhibitors, the compounds of the formula I and the pharmaceutically acceptable salts and prodrugs thereof are suitable for the prevention and treatment of chemokine mediated diseases.
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Page/Page column 114-115
(2008/06/13)
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- A practical synthesis of C2-symmetric chiral binaphthyl ketone catalyst
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A practical synthesis of 11-membered C2-symmetric binaphthyl ketone (R)-1, a catalyst for asymmetric epoxidation, was developed. (±)-1,1'-Binaphthyl-2,2'-dicarboxylic acid [(±)-6] was efficiently resolved by (R)-(-)-1-cyclohexylethylamine to give (R)-6 in >99% ee and in 38% yield. Condensation of the acid chloride derived from (R)-6 with 1,3-dihydroxyacetone dimer at 60-70 °C provided the desired chiral ketone (R)-1 in 61-63% yield without need for high dilution techniques.
- Seki,Yamada,Kuroda,Imashiro,Shimizu
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p. 1677 - 1680
(2007/10/03)
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- Enantioselective dihydroxylation of olefins by osmium tetroxide in the presence of an optically active 1,1'-binaphthyl diamine derivative
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The chiral diamine (S)-1, introduced by Cram and Mazaleyrat, has been reprepared following a different sequence which involves the resolution of diacid (RS)-3. The e.e. (via HPLC and NMR), the absolute configuration (via CD) and the most stable conformation (via UV and molecular mechanics calculations) of (S)-1 have been determined. (S)-1 has been employed as a chiral auxiliary in the stoichiometric syn-dihydroxylation of olefins obtaining optically active 1,2-diols with e.e.s up to 98%.
- Rosini, Carlo,Tanturli, Roberto,Pertici, Paolo,Salvadori, Piero
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p. 2971 - 2982
(2007/10/03)
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- Enantioselective catalysis of the triplex diels-alder reaction: A study of scope and mechanism
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Irradiation of the chiral sensitizers 1,1-bis(2,4-dicyanonaphthalene) and 1,r-bis(2,10-dicyanoanthracene) catalyzes the triplex Diels-Alder reaction of trans-β-methylstyrene with 1,3-cyclohexadiene to form the [4 + 2] cycloadducts endo-trans-6-methyl-5-phenylbicyclo[2.2.2]oct-2-ene. When the sensitizer is optically active and the irradiation is performed at low temperature in ether or toluene solution, the [4 + 2] cycloadducts are formed enantioselectively. The mechanism of the enantioselective triplex Diels-Alder reaction was examined by chemical and spectroscopic means. Interaction of the chiral sensitizer with the prochiral styrene forms diastereomeric exciplexes. The equilibration of these exciplexes is fast at room temperature but not at low temperature. The exciplexes react with diene to form a triplex. This reaction leads to cycloadduct formation. Enantioselection is a consequence of different trapping efficiencies for the diastereomeric exciplexes by diene.
- Kim, Ji-In,Schuster, Gary B.
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p. 9309 - 9317
(2007/10/02)
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- A Novel Clathrate Design: Selective Inclusion of Uncharged Molecules via the Binaphthyl Hinge and Appended Coordinating Groups. X-ray Crystal Structures and Binding Modes of 1,1'-Binaphthyl-2,2'-dicarboxylic Acid Host/Hydroxylic Guest Inclusions
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1,1'-Binaphthyl-2,2'-dicarboxylic acid (1) is demonstrated as a novel type of clathrate host whose main mode of action is derived from a combination of the steric barrier and the coordinative interaction principle which constitutes the new "coordinatoclathrate" strategy.Inclusion properties of the crystal lattice of 1 are revealed for a variety of uncharged organic guest molecules (30 examples), ranging from OH-, to NH-, to CH-acidic compounds such as alcohols, carboxylic acids, amides, and nitriles to rather unpolar compounds like bromobenzene and toluene.Marked discrimination selectivities in the clathrate formation from solvent mixtures are found in regard to the group functionality, the substitution pattern, and the molecular size of the guest species, making accessible a simple process for chemical compound separation.The stoichiometries and the increased-temperature as well as the reduced-pressure stabilities of the various clathrates are discussed.The principles of stucture of five different alcohol clathrates of 1 are determined with the aid of X-ray structure analysis at 273 K: 1*2MeOH (10) 1/n, a = 15.642 Angstroem, b = 14.532 Angstroem, c = 9.292 Angstroem, β = 95.14 deg, Z = 4>; 1*2EtOH (11) ; 1*2(2-PrOH) (13) ; 1*2-BuOH (15) 1/n, a = 12.009 Angstroem, b = 12.747 Angstroem, c = 14.982 Angstroem, β = 105.52 deg, Z = 4>; 1*ethylene glycol (24) 1/n, a = 14.276 Angstroem, b = 9.533 Angstroem, c = 15.556 Angstroem, β = 109.19 deg, Z = 4>.In all these cases, however, hydroxyl groups of the host molecules were found to be intercalated via large pseudo-ring formation between the carboxyl functions of at least two host units of opposite chirality with a different mode of hydrogen bridging.Depending on the host:guest stoichiometry (1:1 or 1:2) and on the nature of the guest molecules, these entities consist of three, four, or eight moieties (COOH, OH).The direction of the strong and cooperative bonds is always homodromic.The shape and the size of the cleft formed in the matrix of cooperating host moieties are shown to vary, matching the specific needs of coordinating interactions (hydrogen bonding) and topological requirements (branching, e.g.) of the guest species.
- Weber, Edwin,Csoregh, Ingeborg,Stensland, Brigitta,Czugler, Matyas
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p. 3297 - 3306
(2007/10/02)
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