5216-37-5Relevant articles and documents
Efficient deep blue emission by 4-styrylbenzonitrile derivatives in solid state: Synthesis, aggregation induced emission characteristics and crystal structures
Fang, Ying,Meng, Yuanyuan,Yuan, Chunming,Du, Chunhui,Wang, Kun-Peng,Chen, Shaojin,Hu, Zhi-Qiang
, (2021/11/16)
Organic fluorescent molecules with π-conjugated system have shown great importance in numerous applications including bioimaging and optoelectronics. Planar aggregation-induced emissive (AIE) organic compounds with efficient solid-state luminescence are rarely developed and urgently needed in various applications. In this work, highly planar 4-styrylbenzonitrile derivatives have been synthesized. Most of these compounds show strong AIE properties with hundred-fold fluorescent enhancement. Moreover, these molecules are deep blue emissive in solid state, exhibiting good to excellent fluorescence quantum efficiency. The single crystal analysis shows that adjacent molecules could form special J-type aggregation. The intramolecular rotations are efficiently restricted by various noncovalent interactions. These molecular arrangements could be essential for the observed strong emission in aggregated and solid state. This work has paved a new path to efficient AIE-active organic emitters with highly planar conformations from 4-styrylbenzonitrile structure.
Effect of substituents on TiO2 photocatalytic oxidation of trans-stilbenes
Miyake, Teruyuki,Hashimoto, Yuichiro,Jinnai, Seihou,Oketani, Ryusei,Higashida, Suguru
, p. 55 - 60 (2019/01/29)
Photocatalytic reaction of trans-stilbene on TiO2 particles produces benzaldehyde with high selectivity in acetonitrile-water mixed solvent. Introduction of electron-donating substituents to the benzene rings accelerated the reaction. On the other hand, the rate was decelerated by electron-withdrawing substituents. These results suggest that the reaction proceeds by hydroperoxo or hydroperoxy, which were formed on TiO2 surface by UV irradiation, rather than free OH radicals.
SYNTHESIS OF ALKENES FROM PHOSPHAALKENES AND CARBONYL COMPOUNDS
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Page/Page column 14; 15; 17, (2018/05/24)
The present invention is a method for the reductive coupling of carbonyl compounds to selectively prepare unsymmetrical alkene(s). In a first step of the method according to the invention, a phosphorus reagent, such as a phosphanylphosphonate, a phosphoranylidenephosphane, or a silylphosphane, is used to convert the first carbonyl compound to a λ3 σ2 phosphaalkene intermediate. This phosphaalkene intermediate is activated by the addition of a base such as hydroxide or alkoxide, potentially under oxidizing conditions, and then reacted with a second carbonyl compound to form the alkene. The first and the second carbonyl compounds may be different from each other, substituted and selected from the group consisting of aldehydes, such as aromatic or aliphatic aldehyde, or ketones, such as aromatic or aliphatic ketones. In such a case, an unsymmetrical alkene is selectively formed. The invention also embraces any alkene compound prepared as taught by the present application. Another aspect of the invention is a kit of parts for the reductive coupling of a first and a second (substituted) carbonyl compound to selectively prepare unsymmetrically substituted alkene(s).
Oxidative Dephosphorylation of Benzylic Phosphonates with Dioxygen Generating Symmetrical trans-Stilbenes
Huang, Tianzeng,Chen, Tieqiao,Han, Li-Biao
, p. 2959 - 2965 (2018/03/09)
Under a dioxygen atmosphere, benzylphosphonates and related phosphoryl compounds can readily produce the corresponding trans-stilbenes in high yields with high selectivity upon treatment with bases. Various functional groups were tolerable under the reaction conditions.
Coordination-driven hierarchical organization of π-conjugated systems: From molecular to supramolecular π-stacked assemblies
Yao, Yishan,Shen, Wenting,Nohra, Brigitte,Lescop, Christophe,Reau, Regis
experimental part, p. 7143 - 7163 (2010/09/05)
The reaction of U-shaped, bimetallic, CuI complexes, assembled from a heteroditopic pincer, with cyano-capped π-conjugated linkers gives a straightforward access to πstacked metallocyclophanes in good yields. In these assemblies, the π-walls ha
Synthesis of novel sulfonyl-stabilized phosphorus ylides, and the kinetics and mechanism of their conventional and flash vacuum pyrolysis reactions
Al-Bashir, Rasha F.,Al-Awadi, Nouria A.,El-Dusouqui, Osman M.E.
, p. 1543 - 1553 (2007/10/03)
Nine substituted sulfonyl-stabilized phosphorus ylides were prepared by treating their intermediate ylide analogues with phenylmethanesulfonyl fluoride. The stoichiometric ratio of the reactants for each preparation needed to be adjusted according to the basicity of each ylide intermediate. The nine ylide compounds were then subjected to conventional (sealed-tube) gas-phase pyrolysis at 470-545 K. The pyrolytic reactions were homogeneous and obeyed a first-order rate equation. The values of the Arrhenius log A (s-1) and E a (kJ mol-1) obtained for these reactions averaged 11.12 ± 2.00 and 131.8 ± 24.4, respectively. Analysis of the pyrolysates from conventional pyrolysis and from flash vacuum pyrolysis at 600 K showed the products to be complex mixtures of triphenylphosphine, triphenylphosphine oxide, triphenylphosphine sulfide, and symmetric and unsymmetric alkenes. Conventional pyrolysis also gave novel mixed sulfones and, for the p-methoxyaryl substituent, p-anisaldehyde. The products of the reactions under study are explained on the basis of a mechanism involving a sulfonyl carbene intermediate, and the reaction mechanism is used to rationalize the kinetic results and molecular reactivities.
Synthesis of stilbenes via homocoupling of aryl aldehyde tosylhydrazones
Kabalka, George W,Wu, Zhongzhi,Ju, Yuhong
, p. 4759 - 4760 (2007/10/03)
Stilbenes are readily prepared in good yields via homocoupling of aryl aldehyde tosylhydrazones in the presence of lithium tert-butoxide and trimethyl borate under reflux in THF.
Mesogenic glycidyl esters
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, (2008/06/13)
Glycidyl esters are disclosed which contain mesogenic moieties which result in improved properties when cured.
Evaluation of the selectivity of the epoxidation of cis- versus trans-alkenes by oxo[meso-tetrakis(2,6-dibromophenyl)porphinato]chromium(V). Dynamics, products, and van der Waals energies
He, Gong-Xin,Mei, Houng-Yau,Bruice, Thomas C.
, p. 5644 - 5650 (2007/10/02)
Studies of the reaction of oxo[meso-tetrakis(2,6-dibromophenyl)porphinato]chromium(V) [(Br8TPP)CrV(O)(X)] with a number of trans-alkenes have been carried out with the objective of clarifying the nature of the reported stereoselectivity of the epoxidation of cis-alkenes as compared to trans-alkenes. The alkenes employed were trans-p,p′-dimethoxystilbene, trans-stilbene, trans-β-methylstyrene, trans-p,p′-dicyanostilbene, trans-2-pentene, trans-5-decene, trans-2-hexenyl acetate, (E)-1,2-bis(trans-2,trans-3-diphenylcyclopropyl)ethene, and also (Z)-1,2-bis(trans-2,trans-3-diphenylcyclopropyl)ethene. The influence of electronic and steric factors in determining the second-order rate constants (k1) for the reactions of trans-alkenes with (Br8TPP)CrV(O)(X) were separated by use of the linear free-energy relationship of log k1 and the one-electron oxidation potentials (E1/2) established by the reaction of a series of cis-alkenes with (Br8TPP)CrV(O)(X). Quantification of the steric factors established that there is no appreciable steric retardation of the second-order rate constants for reaction of trans-p,p′-dimethoxystilbene, trans-β-methylstyrene, trans-2-pentene, trans-5-decene, and trans-2-hexenyl acetate with (Br8TPP)CrV(O)(X). Steric hindrance is quite marked with trans-stilbene, trans-p,p′-dicyanostilbene, and (E)-1,2-bis-(trons-2,trans-3-diphenylcyclopropyl)ethene. In comparison with trans-stilbene, the lack of a kinetic steric effect with trans-p,p′-dimethoxystilbene requires a change of mechanism. The standard free energy (ΔGo) for one-electron oxidation of trans-p,p′-dimethoxystilbene [(Br8TPP)CrV(O)(X) + >C=C8TPP)CrIV(O)(X) + >C+C?o values for trans-stilbene and cis-stilbene by 0.46 and 0.59 V, respectively. Thus, trans-p,p′-dimethoxystilbene but not trans-stilbene can undergo facile le- oxidation by (Br8TPP)CrV(O)(X). This can be shown to be allowed by comparison of ΔGo and ΔGa values. One-electron transfer can take place at significantly longer distances than can covalent bond formation. Computer docking experiments have defined the stereochemistry associated with the closest approach of minimal van der Waals repulsive forces in the reaction of trans- and cis-stilbene. For trans-stilbene the closest approach is at a distance of 3.88 A? from directly above the CrV(O) while for cis-stilbene lowest energy closest approach is at 2.81 A? with the C=C bond: (i) lined parallel to opposite meso carbons; and (ii) above the CrV(O) oxygen with an offset (α) from the perpendicular CrV-O bond of α = 24°. Product yields are in accord with assigned steric effects and the nature of the products and mode of formation are discussed.
