30752-19-3Relevant articles and documents
Alkyloxy modified pyrene fluorophores with tunable photophysical and crystalline properties
Kapf, Andreas,Eslahi, Hassan,Blanke, Meik,Saccone, Marco,Giese, Michael,Albrecht, Marcel
supporting information, p. 6361 - 6371 (2019/04/25)
Novel alkyloxy modified 2,7-di-tert-butyl-4,5,9,10-tetra(arylethynyl)pyrenes were prepared through a straightforward Sonogashira coupling approach. Optical properties such as quantum yields and absorption/emission spectra of the fluorophores were investigated by UV/Vis and fluorescence measurements. Aggregation induced excimer formation of the chromophores in polar solvents and in the solid state was proved by the presence of a characteristic bathochromically shifted emission band and a decrease of the emission capability. These results strongly indicate the unexpected observation that the excimer formation of adjacent pyrene rings is not prevented by the introduction of bulky tert-butyl substituents. Single-crystal X-ray and computational analyses reveal the co-planar alignment of adjacent molecules and the presence of π-π-stacking in the molecular packing of the pyrene polyaromatics. Furthermore, fluorescence, DSC and POM measurements indicate that the aggregation behaviour, the thermal characteristics and the crystalline properties are significantly influenced by changing structural features of the attached functional groups at the periphery of the pyrene core.
Semiheterogeneous Dual Nickel/Photocatalytic (Thio)etherification Using Carbon Nitrides
Cavedon, Cristian,Madani, Amiera,Seeberger, Peter H.,Pieber, Bartholom?us
supporting information, p. 5331 - 5334 (2019/07/08)
A carbon nitride material can be combined with homogeneous nickel catalysts for light-mediated cross-couplings of aryl bromides with alcohols under mild conditions. The metal-free heterogeneous semiconductor is fully recyclable and couples a broad range of electron-poor aryl bromides with primary and secondary alcohols as well as water. The application for intramolecular reactions and the synthesis of active pharmaceutical ingredients was demonstrated. The catalytic protocol is applicable for the coupling of aryl iodides with thiols as well.
Derivative based on 1,3,5-triazine and fluorene unit and application thereof
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Paragraph 0037; 0039, (2018/09/12)
The invention relates to a derivative based on a 1,3,5-triazine structure and a fluorene unit and application thereof. The 1,3,5-triazine derivative and the fluorenyl derivative are fixed into a single molecule through sp3 hybrid carbon atoms by means of a Pd(dba)2 catalytic C-H coupled reaction, and a bipolar body material is prepared. The synthesis method is simple, raw materials are easy to obtain, and industrial development is facilitated. The bipolar body material has the balanced carrier transport capability, the high triplet energy level, the wide energy gap and the high quantum efficiency. According to the bipolar body material, under the film state, due to the interplanar pi-pi effect of the 1,3,5-triazine, excimer fluorescence spectrum red shifting is formed. The body material has the good solubility in a common organic solvent and can be applied to preparing a solution machined electroluminescent device. The body material is applied to the electroluminescent device, the device efficiency is improved, driving voltage and efficiency roll-off are lowered, and the service life of the device is prolonged.
Thermotropic MIDA Boronates as a Case Study for the Role of Dipolar Interactions in Liquid Crystalline Self-Assembly
W?hrle, Tobias,Gündemir, Rafet,Frey, Wolfgang,Knecht, Friederike,K?hn, Andreas,Laschat, Sabine
supporting information, p. 4149 - 4159 (2017/03/31)
A series of MIDA (N-methylimino diacetic acid) boronates carrying 4-alkoxy, 3,4-bisalkoxy, or 3,4,5-trisalkoxyphenyl substituents were synthesized and their mesomorphic properties characterized by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X-ray diffraction (XRD) techniques such as small- and wide-angle X-ray scattering (SAXS and WAXS, respectively). Most derivatives were liquid crystalline. In the case of mono- and bisalkoxy-substituted derivatives, C6 chains already induced smectic A (SmA) mesophases despite the bulky MIDA head group. With increasing chain length, columnar hexagonal (Colh) phases replaced SmA phases in the disubstituted series. Quantum chemical calculations on a series of MIDA boronates show that the B?N bond is a dative bond with a positive charge on the boron atom and negative charges on the nitrogen and oxygen atoms. In addition, no π-interaction between the aryl moiety and B?N bond was found, thus the mesogenic unit is electronically decoupled from the MIDA head group. These theoretical findings were supported by IR and Raman spectra as well as by asingle crystal structure analysis of 4-ethoxyphenyl MIDA boronate. Calculations of the electrostatic potential of the MIDA boronate reveal a special polarity pattern that can support the formation of a two-dimensional network and is likely to explain the liquid crystalline self-assembly. The absence of any electronic cross-talk between the MIDA head group and B-aryl or B-alkyl substituents allows the efficient tailoring of the mesophase type through variation of the substituents.
Probing the Hydrophobic Binding Pocket of G-Protein-Coupled Lysophosphatidylserine Receptor GPR34/LPS1 by Docking-Aided Structure-Activity Analysis
Sayama, Misa,Inoue, Asuka,Nakamura, Sho,Jung, Sejin,Ikubo, Masaya,Otani, Yuko,Uwamizu, Akiharu,Kishi, Takayuki,Makide, Kumiko,Aoki, Junken,Hirokawa, Takatsugu,Ohwada, Tomohiko
supporting information, p. 6384 - 6399 (2017/08/02)
The ligands of certain G-protein-coupled receptors (GPCRs) have been identified as endogenous lipids, such as lysophosphatidylserine (LysoPS). Here, we analyzed the molecular basis of the structure-activity relationship of ligands of GPR34, one of the LysoPS receptor subtypes, focusing on recognition of the long-chain fatty acid moiety by the hydrophobic pocket. By introducing benzene ring(s) into the fatty acid moiety of 2-deoxy-LysoPS, we explored the binding site's preference for the hydrophobic shape. A tribenzene-containing fatty acid surrogate with modifications of the terminal aromatic moiety showed potent agonistic activity toward GPR34. Computational docking of these derivatives with a homology modeling/molecular dynamics-based virtual binding site of GPR34 indicated that a kink in the benzene-based lipid surrogates matches the L-shaped hydrophobic pocket of GPR34. A tetrabenzene-based lipid analogue bearing a bulky tert-butyl group at the 4-position of the terminal benzene ring exhibited potent GPR34 agonistic activity, validating the present hydrophobic binding pocket model.
Double thiopheneglyoxylic [...] and derivatives and preparation method
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Page/Page column 15, (2016/10/07)
The invention discloses bithienofluorene, its derivative and a preparation method. The compounds are characterized in that: a fluorene ring is in connection with thieno rings, and the 2- position of thiophene has a substituent group, which can be hydrogen, alkyl or aryl. The preparation method consists of: taking 2, 7-dyhydroxyl-9-fluorenone as a raw material, employing sulfonyl chloride to conduct chlorination so as to synthesize 3, 6-dichloro-2, 7-dyhydroxyl-9-fluorenone; and then adopting trifluoromethanesulfonic anhydride to carry out esterification, and performing a Sonogashira coupling reaction to obtain series of 2, 7-disubstituted ethynyl-3, 6-dichloro-9-fluorenone, and finally conducting ring closing by sodium sulfide and reduction to obtain bithienofluorene and its derivative. The series of compounds involved in the invention provides a new option for organic field effect transistor materials, and the preparation method provides a new method for aromatic ketone carbonyl reduction.
Synthesis and Characterization of a New Series of Paramagnetic Ferroelectric Liquid Crystalline Nitroxide Radicals
Uchida, Yoshiaki,Tamura, Rui,Suzuki, Katsuaki,Takahashi, Hiroki,Aoki, Yoshio,Nohira, Hiroyuki
, p. 89 - 106 (2015/09/01)
A new series of all-organic liquid-crystalline (LC) chiral radical compounds,trans-1-alkoxyphenyl-4-[(4-(4-alkoxyphenyl)-2,5-dimethylpyrrolidine-1-oxy-2-yl)-benzylideneamino]benzenes (1) with various alkyl chains, containing a chiral nitroxide unit in the mesogen core were synthesized and their LC properties were fully characterized. The enantiomerically enriched compounds (2S,5S)-1 showed N, TGBA, SmA and SmC phases, while the racemates (±)-1 exhibited N, SmA and SmC phases. The phase transition behavior and the ferroelectric properties of the SmC phase of (2S,5S)-1 differed from those of previously reported analogues with an ester group as a substitute for the imino group of (2S,5S)-1. Some of the (2S,5S)-1 series showed a temperature-dependent spontaneous polarization PS (θ) inversion. We discuss the origin of this difference in terms of their molecular structures optimized by molecular orbital calculations. The phase transition behavior supports the hypothesis that the large φ, which is defined as the angle between the molecular long axis (one of the principal axes of inertia) and the direction of the dipole moment in each molecule, results in the stabilization of the SmA (SmA) phase.
CYCLOHEXADIENE FULLERENE DERIVATIVES
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Page/Page column 78; 79, (2015/03/28)
The invention relates to novel fullerene derivatives, to methods for their preparation and educts or intermediates used therein, to mixtures and formulations containing them, to the use of the fullerene derivatives, mixtures and formulations as organic semiconductors in, or for the preparation of, organic electronic (OE) devices, especially organic photovoltaic (OPV) devices and organic photodetectors (OPD), and to OE, OPV and OPD devices comprising, or being prepared from, these fullerene derivatives, mixtures or formulations.
Copper and l-sodium ascorbate catalyzed hydroxylation and aryloxylation of aryl halides
Song, Guang-Lin,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
supporting information, p. 8823 - 8829 (2015/10/20)
CuSO4·5H2O and NaAsc catalyzed hydroxylation and C-O/C-S cross-coupling reactions of aryl halides with phenols or 4-methylbenzenethiol were described. A wide range of substrates and test cases highlight the synthetic utility of the approach. A series of phenols, diaryl ethers, alkylaryl ethers, and diaryl thioethers were synthesized in high yield.
