- Synthesis of C3-Symmetric star-shaped molecules containing 1,3-azoles via hetero-aryl Heck coupling
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We have demonstrated a useful synthetic strategy to assemble star-shaped C3-symmetric molecules containing 1,3-azole moieties at the periphery. To generate these C3-symmetric heterocycles, we have employed the Pd/Cu-based coupling reactions. To this end, we have used benzoxazole, benzothiazole, and benzimidazole as coupling partners to generate the corresponding hetero-aryl Heck coupling products.
- Kotha, Sambasivarao,Todeti, Saidulu
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p. 1359 - 1363
(2019/02/06)
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- Synthesis of C3-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step
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We demonstrate a new synthetic strategy toward star-shaped C3-symmetric molecules containing α-amino acid (AAA) derivatives and dipeptides. In this regard, trimerization and Negishi cross-coupling reactions are used as the key steps starting fr
- Kotha, Sambasivarao,Todeti, Saidulu
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p. 371 - 377
(2019/02/20)
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- Selective and reversible interconversion of nanosliders commanded by remote control: Via metal-ion signaling
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A multi-device network mainly consisting of two two-component nanosliders was formed by self-sorting of six components. Addition/removal of zinc(ii) ions reversibly reorganized the network by chemical signaling involving the translocation of copper(i) from a relay station followed by the selective disassembly/assembly of one of both multi-component devices. The thus liberated machine parts served to erect a three-component nanoslider alongside the other unchanged two-component nanoslider.
- Saha, Suchismita,Biswas, Pronay Kumar,Paul, Indrajit,Schmittel, Michael
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supporting information
p. 14733 - 14736
(2019/12/24)
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- Electrical and electrochemical properties of lithium solvated electron solutions derived from 1,3,5-triphenylbenzenes
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A series of 1,3,5-triphenylbenzenes (TPBs) bearing various substituents have been made and their ability to form lithium solvated electron solutions (LiSESs) in tetrahydrofuran (THF) solution have been studied. It was found that the TPBs bearing electron
- Lunchev, Andrey V.,Tan, Kim Seng,Grimsdale, Andrew C.,Yazami, Rachid
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supporting information
p. 15678 - 15683
(2018/10/04)
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- Sulfated tungstate catalyzed synthesis of C3-symmetric 1,3,5-triaryl benzenes under solvent-free condition
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Sulfated tungstate catalyzed environmentally benign, simple, one pot, and solvent-free method has been developed for the synthesis of 1,3,5-triarylbenzenes via cyclic self-condensation of three molecules of aryl ketones. High yields, short reaction time, easy work-up procedure and recycling of the catalyst endorse advantage.
- Wagh, Ganesh D.,Akamanchi, Krishnacharya G.
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supporting information
p. 3032 - 3036
(2017/07/17)
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- Structure-property relationships of star-shaped blue-emitting charge-transporting 1,3,5-triphenylbenzene derivatives
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Three star-shaped derivatives of 1,3,5-triphenylbenzene bonded to fluorene moieties with various linking groups were designed and synthesized. The three dendritic compounds are characterized by high values of decomposition temperature (up to 434 °C) and f
- Kukhta, Nadzeya A.,Volyniuk, Dmytro,Peciulyte, Laura,Ostrauskaite, Jolita,Juska, Gytis,Grazulevicius, Juozas V.
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p. 122 - 132
(2015/03/18)
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- Alcohol-soluble electron-transport small molecule for fully solution-processed multilayer white electrophosphorescent devices
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A novel alcohol-soluble electron-transport material was designed and synthesized. This material not only possesses a high triplet energy and a low HOMO level but also exhibits excellent electron-transport properties and good film-forming ability. Efficien
- Jiang, Wei,Xu, Huange,Ban, Xinxin,Yuan, Guolong,Sun, Yueming,Huang, Bin,Duan, Lian,Qiu, Yong
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supporting information
p. 1140 - 1143
(2014/03/21)
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- Novel self-assembled 2D networks based on zinc metal ion co-ordination: Synthesis and comparative study with 3D networks
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The synthesis of linear and trigonal terpyridine bearing molecules (tpys) and their self-assembly to form novel extended self-assembled 2D networks of trigonal tpys with linear tpys through zinc metal ion (Zn2+) co-ordination is reported. The r
- Rajwar, Deepa,Liu, Xinfeng,Lim, Zheng Bang,Cho, Sung Ju,Chen, Shi,Thomas, Jens M. H.,Trewin, Abbie,Lam, Yeng Ming,Sum, Tze Chien,Grimsdale, Andrew C.
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p. 17680 - 17693
(2014/05/06)
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- Modular syntheses of star-shaped pyridine, bipyridine, and terpyridine derivatives by employing sonogashira reactions
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A simple and flexible synthesis for a series of star-shaped pyridine, bipyridine, and terpyridine derivatives is reported by using a modular approach that combines the use of a ligand, spacer, and core unit. A fairly efficient method to prepare 4′-nonafloxy-functionalized terpyridine derivatives is described. The building blocks that contain the functionalized pyridine, bipyridine, or terpyridine derivatives were linked to different C3-symmetrical core units. In most cases, Sonogashira reactions were employed in the crucial final steps of the synthesis. A star-shaped dodecafluorinated compound was also prepared in a straightforward fashion. A simple procedure for the preparation of partially silylated 1,3,5-triethynylbenzene derivatives is presented, which provides an approach to C2-symmetrical star-shaped compounds that have only one terpyridine and two terphenyl units as "dummy" ligands. The absorption and emission spectra of the fully conjugated C3-symmetrical pyridine derivatives were systematically investigated, and fairly large Stokes shifts were observed.
- Trawny, Daniel,Kunz, Valentin,Reissig, Hans-Ulrich
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supporting information
p. 6295 - 6302
(2015/03/30)
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- Highly efficient synthesis of substituted benzenes in the presence of B(HSO4)3 as a new and reusable catalyst under solvent-free conditions
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A highly efficient and simple procedure for the synthesis of substituted benzenes is described. A broad range of ketones (alkyl-aryl ketones and cyclic ketones) were condensed via a cyclotrimerization reaction in the presence of catalytic amounts of boron sulfonic acid [B(HSO4)3], a new, highly efficient, and reusable catalyst, under solvent-free conditions. All reactions completed in short times without formation of any by-products. The catalyst was recovered and reused successfully for 15 cycles of the reaction. Copyright
- Safaei, Hamid Reza,Davoodi, Mansooreh,Shekouhy, Mohsen
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supporting information
p. 2178 - 2190
(2013/07/19)
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- Palladium nanoparticles immobilized on nano-silica triazine dendritic polymer (Pdnp-nSTDP): An efficient and reusable catalyst for suzuki-miyaura cross-coupling and heck reactions
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A new catalyst based on palladium nanoparticles immobilized on nano-silica triazine dendritic polymer (Pdnp-nSTDP) was synthesized and characterized by FT-IR spectroscopy, thermogravimetric analysis, field emission scanning electron microscopy, energy dispersive X-ray, transmission electron microscopy and elemental analysis. The size of the palladium nanoparticles was determined to be 3.1±0.5 nm. This catalytic system showed high activity in the Suzuki-Miyaura cross-coupling of aryl iodides, bromides and chlorides with arylboronic acids and also in the Heck reaction of these aryl halides with styrenes. These reactions were best performed in a dimethylformamide (DMF)/water mixture (1:3) in the presence of only 0.006 mol% and 0.01 mol% of the catalyst, respectively, under conventional conditions and microwave irradiation to afford the desired coupling products in high yields. The Pdnp-nSTDP was also used as an efficient catalyst for the preparation of a series of star- and banana-shaped compounds with a benzene, pyridine, pyrimidine or 1,3,5-triazine unit as the central core. Moreover, the catalyst could be recovered easily and reused several times without any considerable loss of its catalytic activity. Copyright
- Isfahani, Amir Landarani,Mohammadpoor-Baltork, Iraj,Mirkhani, Valiollah,Khosropour, Ahmad R.,Moghadam, Majid,Tangestaninejad, Shahram,Kia, Reza
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p. 957 - 972
(2013/05/08)
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- PH-Controlled reversible formation of a supramolecular hyperbranched polymer showing fluorescence switching
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A π-conjugated AB2 monomer 1 with a dibenzo[24]crown-8 (DB24C8) ring and two secondary amine centres has been synthesised. Treatment of a solution of 1 in dichloromethane with trifluoroacetic acid (TFA) leads to protonation of the amine groups,
- Yu, Bingran,Wang, Baoyan,Guo, Shuwen,Zhang, Qian,Zheng, Xiaorui,Lei, Haitao,Liu, Weisheng,Bu, Weifeng,Zhang, Yun,Chen, Xin
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p. 4922 - 4930
(2013/05/23)
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- DBSA catalyzed cyclotrimerization of acetophenones: An efficient synthesis of 1,3,5-triarylbenzenes under solvent-free conditions
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A facile method for the synthesis of 1,3,5-triarylbenzenes is developed via cyclotrimerization of acetophenones in the presence of 4-dodecylbenzenesulfonic acid (DBSA) as an efficient Bronsted acid catalyst under solvent-free conditions. This synthetic pr
- Prasad, Davinder,Preetam, Amreeta,Nath, Mahendra
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p. 252 - 256
(2013/05/08)
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- Efficient one-step synthesis of C 3-symmetrical benzenoid compounds mediated by SOCl 2/EtOH
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An efficient one-step synthesis of branched functionalized benzenoid compounds from aryl methyl ketones mediated by SOCl2/EtOH is described; some novel C 3-symmetrical molecules were prepared with satisfactory yields. The method enjo
- Zhao, Sanhu,Kang, Lina,Ge, Haixia,Yang, Feifei,Wang, Chenlu,Li, Chang,Wang, Qiang,Zhao, Minggen
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p. 3569 - 3578
(2012/10/30)
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- Nano-silica sulfuric acid catalyzed the efficient synthesis of 1,3,5-triarylbenzenes under microwave irradiation
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Nano-silica sulfuric acid as a heterogeneous, eco-friendly and reusable catalyst was used in the synthesis of 1,3,5-triarylbenzenes via triple-self condensation of acetophenones. All reactions were performed under solventfree conditions and microwave irra
- Ghanbaripour,Mohammadpoor-Baltork,Moghadam,Khosropour,Tangestaninejad,Mirkhani
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p. 791 - 798
(2013/02/22)
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- Microwave-promoted efficient conversion of acetophenones to 1,3,5-triarylbenzenes catalyzed by H3PW12O40 and nano-silica supported H3PW12O40 as reusable catalysts
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H3PW12O40 and nano-silica supported H 3PW12O40 were found to be efficient heterogeneous catalysts for the preparation of 1,3,5-triarylbenzenes via triple self condensation of acetophenones
- Ghanbaripour, Rashid,Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Khosropour, Ahmad R.,Tangestaninejad, Shahram,Mirkhani, Valiollah
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experimental part
p. 721 - 728
(2012/03/12)
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- 1,3,5-Triphenylbenzene fluorophore as a selective Cu2+ sensor in aqueous media
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Three water-soluble fluorophores are synthesized from 1,3,5-tris-(4′- iodophenyl)benzene. The compound with salicylate groups exhibits a selective fluorescent quenching by Cu2+via a static quenching mechanism. The addition of Triton X-100 impro
- Sirilaksanapong, Sakan,Sukwattanasinitt, Mongkol,Rashatasakhon, Paitoon
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supporting information; experimental part
p. 293 - 295
(2012/01/13)
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- Triple condensation of aryl methyl ketones catalyzed by amine and trifluoroacetic acid: Straightforward access to 1,3,5-triarylbenzenes under mild conditions
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An efficient triple condensation reaction of aryl methyl ketones catalyzed by ethylenediamine and trifluoroacetic acid was reported. A broad scope of 1,3,5-triarylbenzenes was obtained in good to excellent yields. The reaction provides a novel and practical approach to access organic materials of polycyclic aromatic hydrocarbons under mild conditions.
- Zhang, Shao-Liang,Xue, Zhao-Feng,Gao, Ya-Ru,Mao, Shuai,Wang, Yong-Qiang
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supporting information; experimental part
p. 2436 - 2439
(2012/06/01)
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- PTSA-catalyzed green synthesis of 1,3,5-triarylbenzene under solvent-free conditions
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An economical and green conversion of acetophenones into 1,3,5-triarylbenzenes catalyzed by PTSA is described. The present method is facile and chemo-selective without using any metal catalyst or solvent.
- Zhao, Yanan,Li, Jian,Li, Chunju,Yin, Kun,Ye, Dongyan,Jia, Xueshun
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supporting information; experimental part
p. 1370 - 1372
(2010/10/03)
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- Highly efficient and novel method for synthesis of 1,3,5-triarylbenzenes from acetophenones
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Heteropolyacid-phosphomolybdic acid has been found to be an efficient and recyclable catalyst for cyclotrimerization of acetophenones into 1,3,5-triarylbenzenes in good yields.
- Phatangare, Kiran,Padalkar, Vikas,Mhatre, Devidas,Patil, Ketan,Chaskar, Atul
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experimental part
p. 4117 - 4121
(2009/12/09)
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- Synthesis and self-assembly of propeller-shaped amphiphilic molecules
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Propeller-shaped aromatic amphiphiles based on a conformationally flexible aromatic segment are shown to self-assemble into well-defined discrete nanostructures with high fluorescence characteristic. The Royal Society of Chemistry.
- Moon, Kyung-Soo,Lee, Eunji,Lee, Myongsoo
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supporting information; experimental part
p. 3061 - 3063
(2009/02/04)
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- Efficient conversion of acetophenones into 1,3,5-triarylbenzenes catalyzed by bismuth(III) trifluoromethanesulfonate tetrahydrate
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Bismuth(III) trifluoromethanesulfonate tetrahydrate is found to efficiently catalyze the cyclotrimerization of acetophenones into 1,3,5-triarylbenzenes in good yields. Georg Thieme Verlag Stuttgart.
- Ono, Fumiaki,Ishikura, Yuichi,Tada, Yuusuke,Endo, Masato,Sato, Tsuneo
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scheme or table
p. 2365 - 2367
(2009/05/07)
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- Organic electroluminescent device
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An organic EL device includes a pair of electrodes, a light emitter layer obtained by mixing a hole transporting material made of a tertiary amine compound, an electron transporting material and a light emitting additive. The tertiary amine compound constituting the hole transporting material has only one oxidation potential as measured by the cyclic voltammetry. A difference in ionization potential between the hole transporting material and electron transporting material of the light emitter layer is 0.35 eV or greater.
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- ORGANIC ELECTRONIC FUNCTIONAL MATERIAL AND USE THEREOF
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The invention provides an organic electronic functional material which comprises a 1,3,5-tris(4-(N,N-diarylamino)phenyl)benzene represented by the general formula (I) wherein A and B are each preferably a phenyl group having an alkyl group of 1-6 carbons or a cycloalkyl group of 5 or 6 carbons at the 4-position.
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- Efficient intermolecular [2 + 2 + 2] alkyne cyclotrimerization in aqueous medium using a ruthenium(IV) precatalyst
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The dimeric bis(allyl)-ruthenium(IV) complex [{Ru(η3:η3-C10H16)(μ-Cl)Cl}2] (C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) was found to catalyze efficiently the [2 + 2 + 2] cyclization of terminal and internal alkynes in aqueous medium. Copyright
- Cadierno, Victorio,Garcia-Garrido, Sergio E.,Gimeno, Jose
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p. 15094 - 15095
(2007/10/03)
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- Synthesis of C3-symmetric nano-sized polyaromatic compounds by trimerization and Suzuki-Miyaura cross-coupling reactions
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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.
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p. 4003 - 4013
(2007/10/03)
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- Nanosized Molecular Propellers by Cyclodehydrogenation of Polyphenylene Dendrimers
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In a polymer analogous approach, large dendritic oligophenylenes containing benzene and tetraphenylmethane cores are transformed via oxidative cyclodehydrogenation to novel propeller-shaped molecules with large polycyclic aromatic hydrocarbon units as "bl
- Simpson, Christopher D.,Mattersteig, Gunter,Martin, Kai,Gherghel, Lileta,Bauer, Roland E.,Raeder, Hans Joachim,Muellen, Klaus
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p. 3139 - 3147
(2007/10/03)
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- Auto-organization of nanostructured organic-inorganic hybrid xerogels prepared from planar precursors by sol-gel processing
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Nanostructured hybrid materials were prepared by sol-gel hydrolysis-polycondensation of 1,3,5-tris(p-triethoxysilylphenyl)benzene PR having a rigid structure and 1,3,5-tris(p-trimethoxysilylpropylphenyl)benzene PF having a planar core connected to three short and flexible arms. Both precursors presented nine directions for solid formation. Their organization was evaluated by birefringence measurements (micrometre scale) and X-ray diffraction studies (nanometre scale). The influence of the planar geometry and the rigidity or flexibility of the organic groups has been studied as well as the effect of changes in experimental conditions. It has been shown that the organization of these solids was less influenced by the experimental parameters than in the case of linear precursors. In the case of the rigid precursor PR, the solids obtained XR had a high intensity of birefringence (7.5-8 × 10-3) and the gels presented cracks whatever the experimental conditions (nucleophile or acid catalysis). In contrast the flexible precursor PF led to solids XF with a lower birefringence (6.2-6.8 × 10-3) and the morphology of the solids in the cells depended on the concentration of catalyst. Interestingly the birefringence appeared without cracks with a lower amount of catalyst and isotropic circular cross-shaped nodules were observed in this case whatever the temperature. The X-ray diffraction diagrams clearly showed that these solids presented a better nanometre scale organization than the gel formed from 1,3,5-tris(trimethoxysilyl)benzene. These observations show that the auto-organization of hybrid materials appears induced by weak van der Waals type interactions as a general phenomenon which is not limited to linear and mesogenic precursors.
- Cerveau, Genevieve,Corriu, Robert J. P.,Framery, Eric,Lerouge, Frederic
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p. 3019 - 3025
(2007/10/03)
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- Rational syntheses of cyclic hexameric porphyrin arrays for studies of self-assembling light-harvesting systems
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Two new cyclic hexameric arrays of porphyrins have been prepared in a rational, convergent manner. The porphyrins in each cyclic hexamer are joined by diphenylethyne linkers affording a wheel-like array with a diameter of ~35 A. One array is comprised of
- Yu,Lindsey
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p. 7402 - 7419
(2007/10/03)
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- Synthesis of 1,3,5-tris[4-(diarylamino)phenyl]benzene and 1,3,5-tris(diarylamino)benzene derivatives
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The title compounds were prepared by the copper catalysed Ullmann coupling of aromatic amines with aromatic aryl iodides. Full spectroscopic details are reported. Solutions of 1,3,5-tris(diarylamino)benzene derivatives in deuterated chloroform undergo hydrogen-deuterium exchange on the central ring and readily turn green owing to partial oxidation by traces of dissolved oxygen. The green colour is quenched by the addition of ascorbic acid. The solutions are more stable in chloroform that has been filtered through basic alumina to remove traces of acid. N-Arylbenzenesulfonamides can be converted to diarylamines by treatment with the sodium salt of an aniline. The Royal Society of Chemistry 2000.
- Plater, M. John,McKay, Murray,Jackson, Toby
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p. 2695 - 2701
(2007/10/03)
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