- Thiophene-containing thiolato dimers, oxygen inserted Cu(II) complex, crystal structures, molecular docking and theoretical studies
-
Reactions of n-butyl- and n-octyl-thiophene with CS2 at 0?°C resulted in thiolate dimers 1 and 2, respectively. The reaction of 1 with Cu(NO3)2·3H2O in methanol under ambient reaction conditions yielded monomeric [CuII{(n-C4H9(C4H2S)CS2O}2] (3). 1 and 3 were authenticated by their single-crystal X-ray crystal structures. Crystal structure of 3 revealed cleavage of the S-S bond of 1 followed by insertion of O-atom, forming a new five-membered Cu–O–S–C–S metallacycle. 1, 2, and 3 were further investigated for their bioactivity through molecular docking with nine different proteins having medicinal implications. Molecular docking of 1, 2 and 3 revealed considerable interaction with different proteins viz. cancer protein Tankyrase 2, influenza viral protein Polymerase subunit PAC–PB1N complex (H5N1), Polymerase subunit PA endonuclease (H1N1), Polymerase subunit PAn Apo(avian influenza), and FTSZ (Bacillus subtilis). Comparatively, 1 has promising application in therapeutics as compared to 2 and 3 based on its inhibitory constant and binding energy. Density functional theory calculations were performed to better understand the bonding of complex using MO diagram in 1–3. Moreover, TDDFT calculations were performed to facilitate the assignment of electronic transitions of UV–Vis spectra.
- Mobin, Shaikh M.,Tauqeer, Mohd.,Mohammad, Akbar,Mishra, Veenu,Kumari, Pratibha
-
-
Read Online
- Ligand assessment for the suzuki-miyaura cross coupling reaction of aryl and heteroaryl bromides with n-butylboronic acid. The advantages of buchwald's s-phos
-
An investigation of biarylphosphine ligands for the Suzuki-Miyaura cross coupling reaction of aryl and heteroaryl bromides with n-butylboronic acid is presented. The results obtained on ligand modification and aryl as well as heteroaryl bromides variation represent a significant improvement in the state of the art of alkylboronic acid cross coupling methodology.
- Jagusch, Thomas,Lehnemann, Bernd,Meudt, Andreas,Nerdinger, Sven,Neuner, Sandro,Scherer, Stefan,Schottenberger, Herwig,Snieckus, Victor
-
p. 631 - 644
(2020/01/31)
-
- CATALYST COMPOSITION INCLUDING NOVEL TRANSITION METAL COMPOUND
-
The present invention relates to a catalyst composition including a transition metal compound represented by the following Formula 1; and one or more of a compound represented by the following Formula 2, a compound represented by the following Formula 3 and a compound represented by the following Formula 4. The catalyst composition according to the present invention has excellent copolymerization properties, and can be usefully used as a catalyst for a polymerization reaction for preparing an olefin-based polymer having a high molecular weight.
- -
-
-
- Palladium-catalyzed regioselective allylation of five-membered heteroarenes with allyltributylstannane
-
Palladium-catalyzed allylation reactions of 2-(chloromethyl)thiophenes, 2-(chloromethyl)furans, and N-protected 2-(chloromethyl)-1H-pyrroles with allyltributylstannane were described in this study. This type of allylation reaction regioselectively occurred on the heteroarene rings to produce allylated dearomatization products or allylated heteroarenes with satisfactory yields.
- Zhang, Sheng,Yu, Xiaoqiang,Feng, Xiujuan,Yamamoto, Yoshinori,Bao, Ming
-
supporting information
p. 3842 - 3845
(2015/03/30)
-
- Functional group tolerant Kumada-Corriu-Tamao coupling of nonactivated alkyl halides with aryl and heteroaryl nucleophiles: Catalysis by a nickel pincer complex permits the coupling of functionalized Grignard reagents
-
A nickel(II) pincer complex [(MeNN2)NiCl] (1) catalyzes Kumada-Corriu-Tamao cross coupling of nonactivated alkyl halides with aryl and heteroaryl Grignard reagents. The coupling of octyl bromide with phenylmagnesium chloride was used as a test reaction. Using 3 mol % of 1 as the precatalyst and THF as the solvent, and in the presence of a catalytic amount of TMEDA, the coupling product was obtained in a high yield. The reaction conditions could be applied to cross coupling of other primary and secondary alkyl bromides and iodides. The coupling is tolerant to a wide range of functional groups. Therefore, alkyl halides containing ester, amide, ether, thioether, alcohol, pyrrole, indole, furan, nitrile, conjugated enone, and aryl halide moieties were coupled to give high isolated yields of products in which these units stay intact. For the coupling of ester-containing substrates, O-TMEDA is a better additive than TMEDA. The reaction protocol proves to be efficient for the coupling of Knochel-type functionalized Grignard reagents. Thus aryl Grignard reagents containing electron-deficient and/or sensitive ester, nitrile, amide, and CF3 substituents could be successfully coupled to nonactivated and functionalized alkyl iodides. The catalysis is also efficient for the coupling of alkyl iodides with functionalized heteroaryl Grignard reagents, giving rise to pyridine-, thiophene-, pyrazole-, furan-containing molecules with additional functionalities. Concerning the mechanism of the catalysis, [(MeNN2)Ni-(hetero)Ar] was identified as an intermediate, and the activation of alkyl halides was found to take place through a radical-rebound process.
- Vechorkin, Oleg,Proust, Valerie,Hu, Xile
-
supporting information; experimental part
p. 9756 - 9766
(2011/03/19)
-
- Synthesis and the effect of alkyl chain length on optoelectronic properties of diarylethene derivatives
-
Photochromic symmetrical diarylethene derivatives 1a-6a bearing different long alkyl chains at 2-position of thiophene rings have been synthesized and their structures have been determined by single-crystal X-ray diffraction analysis. The effect of alkyl chain length on their optoelectronic properties, such as photochromism in solution as well as in the crystalline phase and electrochemical performance was investigated in detail. These diarylethenes have showed good photochromic behavior both in solution and in the single crystalline phase. Introduction of the long alkyl chains at 2-position of bis(5-formyl-3-thienyl)perfluorocyclopentene increased the absorption coefficients of both open- and closed-ring isomers and induced bathochromic shifts of the maximal wavelength absorption of the closed-ring isomers. The long alkyl chains can also decrease the cyclization/cycloreversion quantum yields and the oxidation potentials. The cyclic voltammetry indicated that the band gap of these diarylethene derivatives was significantly affected by the alkyl chain length.
- Zheng, Chunhong,Pu, Shouzhi,Xu, Jingkun,Luo, Mingbiao,Huang, Dechao,Shen, Liang
-
p. 5437 - 5449
(2008/01/07)
-
- Synthesis of end-blocked thienyl oligomers incorporating benzo[c]thiophene
-
A straightforward synthesis of end-capped bithienyl, quaterthienyl and sexithienyl systems incorporating benzo[c]thiophene units is presented.
- Mohanakrishnan, Arasambattu K.,Amaladass,Arul Clement
-
p. 779 - 784
(2007/10/03)
-
- Large area liquid crystal monodomain field-effect transistors
-
Butyl, hexyl, and decyl derivatives of the liquid-crystalline organic semiconductor 5,5″-bis(5-alkyl-2-thienylethynyl)-2,2′:5′, 2″-terthiophene were synthesized and studied with respect to their structural, optical, and electrical properties. By means of an optimized thermal annealing scheme the hexyl and decyl compounds could be processed into self-assembled monodomain films of up to 150 mm in diameter. These were investigated with X-ray diffractometry, which revealed a clearly single-crystalline monoclinic morphology with lamellae parallel to the substrate. Within the lamellae the molecules were found to arrange with a tilt of about 50° with the rubbing direction of the polyimide alignment layer. The resulting, close side-to-side packing was confirmed by measurements of the UV/vis absorption, which showed a dichroic ratio of 19 and indicated H-aggregation. AFM analyses revealed self-affinity in the surface roughness of the monodomain. The compounds showed bipolar charge transport in TOF measurements, with hole mobilities reaching up to 0.02 cm2/Vs and maximum electron mobilities around 0.002 cm2/Vs. The hexyl derivative was processed into large-area monodomain top-gate field-effect transistors, which were stable for months and showed anisotropic hole mobilities of up to 0.02 cm2/Vs. Compared to multidomain bottom-gate transistors the monodomain formation allowed for a mobility increase by 1 order of magnitude.
- Van Breemen, Albert J. J. M.,Herwig, Peter T.,Chlon, Ceciel H. T.,Sweelssen, Joergen,Schoo, Herman F. M.,Setayesh, Sepas,Hardeman, Willie M.,Martin, Christian A.,De Leeuw, Dago M.,Valeton, Josue J. P.,Bastiaansen, Cees W. M.,Broer, Dirk J.,Popa-Merticaru, Andreea R.,Meskers, Stefan C. J.
-
p. 2336 - 2345
(2007/10/03)
-
- 1,4-DITHIENYLBENZENE DERIVATIVE
-
A novel compound having a mesophase forming property or liquid crystallinity and a high level of electric charge mobility, a liquid crystal composition comprising said compound and a charge transfer material comprising the same, and various element using said charge transfer material. The novel compound is a 1,4-dithienylbenzene derivative represented by general formula (I): (I) wherein R1 and R2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, provided that R1 and R2 do not simultaneously represent a hydrogen atom; and A represents a benzene ring optionally having a substituent.
- -
-
Page/Page column 16
(2010/10/20)
-
- Synthesis of C3-symmetric nano-sized polyaromatic compounds by trimerization and Suzuki-Miyaura cross-coupling reactions
-
Various C3-symmetric molecules were prepared by trimerization of acetyl aromatic compounds and subsequently coupled with various boronic acids under Pd0 catalysis conditions to generate oligoaryl/-heteroaryl C3-symmetric molecules. Several furan- and thiophene-containing star-shaped molecules were prepared by the use of Suzuki-Miyaura cross-coupling as a key step. Structural and conformational details were explored by semi-empirical molecular orbital theory using the AM1 method. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Kotha, Sambasivarao,Kashinath, Dhurke,Lahiri, Kakali,Sunoj, Raghavan B.
-
p. 4003 - 4013
(2007/10/03)
-
- Benzylation via Tandem Grignard Reaction - Iodotrimethylsilane (TMSI) Mediated Reduction
-
A method has been developed which allows for the large scale preparation of biarylmethanes.This method involves the initial formation of biarylmethanols via reaction of aryl Grignards with carbonyl compounds followed by a subsequent reduction with iodotrimethylsilane (TMSI).A number of improvements over existing literature procedures are reported as well as previously unobserved dimerizations.Studies reveal that as few as 3 equiv of TMSI will give complete reduction in most cases where either of the substituents are not heteroaromatic.Mono-substituted alkanols react with TMSI to afford the corresponding iodides.A mechanistic study of the TMSI reduction is also reported.
- Stoner, Eric J.,Cothron, Darlene A.,Balmer, Mary K.,Roden, Brian A.
-
p. 11043 - 11062
(2007/10/02)
-
- The Synthesis and Liquid Crystal Properties of Some Series Homologues of 1,2,4-Oxadiazole Derivatives
-
Homologues series of some derivatives of 3,5-(4-substituted phenyl)-1,2,4-oxydiazole were synthesized and their phase behavior studied.Introduction of the pentagonal heteroaromatic ring leads to significant changes in mesomorphic behavior in comparison with analogous compounds containing the phenyl ring.The synthesised compounds exhibit smectic and nematic phases. - Keywords: 1,2,4-oxadiazole, nematic and smectic liquid crystals
- Gallardo, H.,Begnini, I. M.
-
-
- Side-chain Effects on the Fragmentation Behaviour of Alkylthiophenes
-
The processes leading to the fragment ions formed from alkylthiophene molecule ions by benzylic cleavage without and with transfer of one hydrogen from the side-chain to the ring and the influence of additional methyl groups on the relative importance of these two fragmentation reactions were investigated.
- Lange, D.,Budzikiewicz, H.
-
p. 432 - 438
(2007/10/02)
-
- NICKEL-PHOSPHINE COMPLEX-CATALYZED GRIGNARD COUPLING-II; GRIGNARD COUPLING OF HETEROCYCLIC COMPOUNDS
-
A general, versatile method for alkylation and arylation of haloheterocyclic compounds is reported.In the presence of a catalytic quantity of , where dppp stands for Ph2P(CH2)3PPh2, bromothiophenes, halopyridines, haloquinoline, and haloisoquinolines reacted with alkyl and aryl Grignard reagents at room temperature or at ether refluxing temperature to give the cross-coupling products.The coupling reactions has been applied to the synthesis of isoquinoline alkaloids.Reactivities of 2-thienyl and 2-pyridyl Grignard reagents have also been examined.
- Tamao, K.,Kodama, S.,Nakajima, I.,Kumada, M.,Minato, A.,Suzuki, K.
-
p. 3347 - 3354
(2007/10/02)
-