- Triple Oxa[7]helicene with Circularly Polarized Luminescence: Enhancing the Dissymmetry Factors via Helicene Subunit Multiplication
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The development of multiple heterohelicenes with a high luminescence dissymmetry factor (glum) is an appealing yet challenging task. Herein, we disclose the synthesis of a structurally unusual furan-based triple oxa[7]helicene, which represents the first reported triple hetero[7]helicene, via [2+2+2] cyclotrimerization/intramolecular dehydrogenative annulation. Compared to the reported double oxa[7]helicene, the triple oxa[7]helicene exhibits an improved glum value of 1.8 × 10-3, exemplifying the potential of the helicene subunit multiplication approach to enhance the glum of heterohelicenes.
- Zhou, Fulin,Huang, Zhenmei,Huang, Zhongyan,Cheng, Rui,Yang, Yudong,You, Jingsong
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- Anti and Syn Eliminations from 2,3-Dihalo-2,3-dihydrobenzofurans. The Role of the Substrate Structure and the Base-Solvent System on the Reaction Mechanism
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The anti and syn β-eliminations from a series of 31 2,3-dihalo-2,3-dihydrobenzofurans (to give 3-halobenzofuran) have been kinetically investigated in t-BuOK-t-BuOH, in the presence and in the absence of 18-crown-6 ether (18C6), and in EtOK-EtOH.Reaction mechanisms have been assigned on the basis of leaving group, kinetic deuterium isotope, ring substituent (5-chlorine), and β-halogen effects.These data have provided information concerning structure and solvent effect on the mechanism of β-elimination reactions that lead to the following conclusions: (a) an E1cBI mechanism is likely to be operating, regardless of stereochemistry, with chlorine as β-activating atom and fluorine as the leaving group and (b) an E2 reaction is likely to be operating for the opposite structural situation, i. e., with β-fluorine activation and chlorine as the leaving group.The mechanism is likely to change from E2 to E1cBI as the reaction stereochemistry changes from anti to syn and as we move from EtOK-EtOH to t-BuOK-t-BuOH and from here to t-BuOK-t-BuOH-18C6.
- Baciocchi, Enrico,Ruzziconi, Renzo,Sebastiani, Giovanni V.
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- A series of π-extended thiadiazoles fused with electron-donating heteroaromatic moieties: Synthesis, properties, and polymorphic crystals
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π-Extended thiadiazoles 4-8 fused with various electron-donating heteroaromatic moieties have been designed and synthesized. Just like thiadiazoles 1-3 synthesized previously, 4-8 exhibit intramolecular charge-transfer (CT) interactions, moderate-to-good fluorescence quantum yields of up to 0.78, and electrochemical amphoterism. In comparison with 1-3, the benzannulation in thiadiazoles 4-7 moderately extends the p conjugation and significantly increases the stability of the cationic species formed upon electrochemical oxidation. The fluorescence quantum yields increase remarkably from 3 to 6 and 7 due to the efficient suppression of nonradiative intersystem crossing resulting from the benzannulation. The properties of 4-8 strongly reflect the different species annulated to the pyrrole rings, namely benzothiophene, naphthalene, and benzofuran. Eleven crystals, including poly- and pseudopolymorphic crystals of 1 (1-Crys.(Y ) and 1-Crys.(G)), 2 (2-Crys.(O) and 2-Crys.(G)), 4 (4-Crys.(O) and 4-Crys. (G)), and 6 (6-Crys.(O) and 6-Crys.(G)), were obtained and characterized by X-ray crystallography. The fluorescence colors and efficiencies are distinct for each poly- and pseudopolymorph of 1, 2, 4, and 6. It has been suggested that both the extent of the electronic interactions in the π-stacked dimers and the presence of excitonic interactions originating in the 1D face-to-face slipped columns affect the fluorescence wavelengths of the poly- and pseudopolymorphs.
- Kato, Shin-Ichiro,Furuya, Takayuki,Nitani, Masashi,Hasebe, Naoya,Ie, Yutaka,Aso, Yoshio,Yoshihara, Toshitada,Tobita, Seiji,Nakamura, Yosuke
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- Thermally activated delayed fluorescent deep blue light material and preparation method thereof with organic electroluminescent device
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The present invention discloses a thermal activation delayed fluorescent deep blue light material and preparation method thereof and an organic electroluminescent device, the thermal activation delayed fluorescent deep blue light material having the follo
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Paragraph 0091-0095; 0097-0101
(2022/01/08)
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- GLUE DEGRADERS AND METHODS OF USE THEREOF
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Described herein are glue degrader compounds, their various targets, their preparation, pharmaceutical compositions comprising them, and their use in the treatment or prevention of conditions, diseases, and disorders mediated by various target proteins.
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Page/Page column 318
(2021/04/01)
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- Room Temperature C-H Arylation of Benzofurans by Aryl Iodides
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A robust method of room temperature direct arylation for benzofuran is reported. This discovery allows for mild arylation by commercially available aryl iodides with complete C-2 regioselectivity and tolerates a range of functional groups, including heat sensitive groups. Mechanistically, a Heck-type oxyarylation product from a direct arylation process is reported as a key piece of evidence for a carbopalladation intermediate.
- Mayhugh, Amy L.,Luscombe, Christine K.
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supporting information
p. 7079 - 7082
(2021/09/18)
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- POLYCYCLIC AROMATIC DERIVATIVE COMPOUNDS AND ORGANIC LIGHT-EMITTING ELEMENTS USING THE SAME
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PROBLEM TO BE SOLVED: To provide: organic light-emitting compounds used in organic layers of organic light-emitting elements and capable of realizing efficient and long-lasting organic light-emitting elements; and organic light-emitting elements comprising the same. SOLUTION: An organic light-emitting compound is such that Q1 to Q3 are linked by linkers Y and X at specific positions, where Q1 to Q3 are identical to or different from each other and each independently a substituted or unsubstituted C6-50 aromatic hydrocarbon ring or a substituted or unsubstituted C2-50 heteroaromatic ring; each of the linkers Y is one selected from among N-R1, CR2R3, O, S, Se and SiR4R5; the multiple linkers Y are identical to or different from each other; and X is one selected from among B, P and P=O. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0108; 0113-0116
(2020/06/30)
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- POLYCYCLIC AROMATIC COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICES USING THE SAME
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Disclosed are polycyclic aromatic compounds that can be employed in various organic layers of organic electroluminescent devices. Also disclosed are organic electroluminescent devices including the polycyclic aromatic compounds. The organic electroluminescent devices are highly efficient and long lasting and have greatly improved luminous efficiency.
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Paragraph 0074-0075
(2020/06/29)
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- ORGANIC COMPOUND AND ORGANIC LIGHT EMITTING DIODE INCLUDING SAME
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Disclosed herein are an organic light emitting compound represented by [Chemical Formula 1] below and an organic light emitting diode comprising same. In [Chemical Formula 1], the substituents R1 to R5, R11 to R18, R21 to R22, and R31 to R40, the linkers L1 to L3, and m1 and m2 are as defined in the description:.
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Paragraph 0291; 0295-0297
(2020/12/31)
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- ORGANIC ELECTROLUMINESCENT DEVICE
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Disclosed is an organic electroluminescent device that employs a compound represented by Formula A-1 or A-2: and a compound represented by Formula B: The organic electroluminescent device has excellent luminescent properties such as high color purity and long lifetime.
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Paragraph 0080-0081
(2020/12/30)
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- Rhodium-catalyzed Sommelet-Hauser type rearrangement of α-diazoimines: Synthesis of functionalized enamides
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An efficient rhodium catalyzed Sommelet-Hauser type rearrangement of sulfur ylides derived from α-thioesters and N-sulfonyl-1,2,3-triazoles has been successfully accomplished for the synthesis of various functionalized enamides. The developed reaction involves the unprecedented [2,3]-sigmatropic rearrangement of sulfur ylides with the imine motif. Importantly, the method works well with various substituted α-thioesters/-amides/-ketones and substituted N-sulfonyl-1,2,3-triazoles and allows the synthesis of diverse enamide derivatives in good to excellent yields. The reaction was also successfully extended to the one-pot synthesis of enamides from terminal alkynes.
- Anbarasan, Pazhamalai,Ramachandran, Kuppan,Reddy, Angula Chandra Shekar,Reddy, Palagulla Maheswar
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supporting information
p. 5649 - 5652
(2020/06/09)
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- Dioxazolones as masked ester surrogates in the Pd(ii)-catalyzed direct C-H arylation of 6,5-fused heterocycles
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A simple and effective Pd(ii)-catalyzed regioselective C(2)-H arylation of 6,5-fused heterocycles with dioxazolones as a masked ester surrogate under mild conditions is reported. The significance of the arylation is highlighted by the new reactivity demonstrated in dioxazolones via proximal C-H activation of the cyclic carbonate of the hydroxamic acid functionality under protic conditions.
- Saxena, Paridhi,Maida, Neha,Kapur, Manmohan
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supporting information
p. 11187 - 11190
(2019/09/30)
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- Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes
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Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes' intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.
- Fredrich, Sebastian,Bonasera, Aurelio,Valderrey, Virginia,Hecht, Stefan
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supporting information
p. 6432 - 6440
(2018/05/31)
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- NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles
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The pair NaBH4-TMEDA as hydride source and a palladium catalyst in THF prove to be an efficient system for the hydrodehalogenation of halogenated heterocycles with one or more heteroatoms. In general, Pd(OAc) 2-PPh3 rapidly hydrodehalogenates reactive halo-heterocycles such as bromo-pyridines, -quinolines, -thiophenes, -indoles, -imidazoles, etc., at room temperature in very good yields, whereas in most cases PdCl2(dppf) reduces less reactive halides such as chloro-pyridines, -quinolines, -pyrimidines and bromo-indoles, -benzofurans, etc. Moreover, PdCl2(tbpf) shows to be even more active removing the 2- and 5-chlorine from both thiophene and thiazole rings. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene and nitrile substituents. Moreover, with a proper selection of the catalyst it is also possible to obtain a good control in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.
- Chelucci, Giorgio,Figus, Susanna
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p. 191 - 209
(2014/07/21)
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- Benzo[b]furane and benzo[b]thiophene derivatives
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The present invention relates to benzo[b]furane and benzo[b]thiophene derivatives of the general formula IV as the free base or salts thereof and their use.
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Page/Page column 17
(2008/06/13)
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- FURYL COMPOUNDS
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Compounds of formula (I) and pharmaceutically-acceptable salts thereof, wherein Ar and R are as defined in the specification, compositions containing such compounds and the use of such compounds and compositions for use in therapy.
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Page/Page column 20-21
(2008/06/13)
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- Fungicides for the control of take-all disease of plants
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Plant disease caused by soil-borne fungus Gaeumannonyces graminis (Gg) is controlled by applying to the seed or the soil a fungicide which has the following general formula: STR1
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- New Class of Chiral Diphosphine Ligands for Highly Efficient Transition Metal-Catalyzed Stereoselective Reactions: The Bis(diphenylphosphino) Five-membered Biheteroaryls
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The synthesis and application of three examples of a new class of chiral (C2) atropisomeric diphosphines characterized by two interconnected five-membered heteroaromatic rings, with hindered rotation around the interanular bond, are described.Optically pure (+)- and (-)-2,2'-bis(diphenylphosphino)-4,4',6,6'-tetramethyl-3,3'-bibenzothiophene (tetraMe-bitianp) (1a) and the parent unsubstituted system (+)- and (-)-bitianp (1b) were synthesized.They were found to be optically stable at 100 deg C and were successfully employed as ligands in the Ru(II)-catalyzed hydrogenation of α- and β-oxo esters to the corresponding α- and β-hydroxy esters and in the hydrogenation of olefinic substrates.The optical and chemical yields were comparable with those reported for the same Ru(II)-binap-catalyzed reactions carried out under the same experimental conditions.The 2,2'-bis(diphenylphosphino)-3,3'-bibenzofuran (1c), the oxygenated analogue of bitianp, was found to be configurationally unstable at room temperature.Complete structural X-ray elucidation of the Pd complexes of 1a-c is reported.The advantages of these biheteroaromatic ligands over the classical biaryl systems are discussed.
- Benincori, Tiziana,Brenna, Elisabetta,Sannicolo, Franco,Trimarco, Licia,Antognazza, Patrizia,et al.
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p. 6244 - 6251
(2007/10/03)
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