DBSA catalyzed cyclotrimerization of acetophenones: An efficient synthesis of 1,3,5-triarylbenzenes under solvent-free conditions

Prasad, Davinder; Nath, Mahendra

doi:10.1016/j.crci.2012.12.008

Cited by 24 publications

(9 citation statements)

References 45 publications

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“…On the other hand, 1,3,5-tris(4-bromophenyl)benzene was synthesized from 4-bromoacetophenone using H 2 SO 4 (conc.) and K 2 S 2 O 7 as the catalytic system following the procedure reported by Prasad et al [ 39 ]. N -benzoyl dithieno[3,2-b:2′,3′-d]pyrrole (monomer 3) was prepared via an amidation reaction by using copper(I) iodide and DMEDA as the catalytic system in the presence of K 2 CO 3 at the reflux temperature for 24 h [ 15 ].…”

Section: Resultsmentioning

confidence: 99%

N-Benzoyl dithieno[3,2-b:2′,3′-d]pyrrole-based hyperbranched polymers by direct arylation polymerization

Nguyen

Tran

et al. 2017

Chemistry Central Journal

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BackgroundAlthough poly(N-acyl dithieno[3,2-b:2′,3′-d]pyrrole)s have attracted great attention as a new class of conducting polymers with highly stabilized energy levels, hyperbranched polymers based on this monomer type have not yet been studied. Thus, this work aims at the synthesis of novel hyperbranched polymers containing N-benzoyl dithieno[3,23,2-b:2′,3′-d]pyrrole acceptor unit and 3-hexylthiophene donor moiety via the direct arylation polymerization method. Their structures, molecular weights and thermal properties were characterized via 1H NMR and FTIR spectroscopies, GPC, TGA, DSC and XRD measurements, and the optical properties were investigated by UV–vis and fluorescence spectroscopies.ResultsHyperbranched conjugated polymers containing N-benzoyl dithieno[3,23,2-b:2′,3′-d]pyrrole acceptor unit and 3-hexylthiophene donor moiety, linked with either triphenylamine or triphenylbenzene as branching unit, were obtained via direct arylation polymerization of the N-benzoyl dithieno[3,23,2-b:2′,3′-d]pyrrole, 2,5-dibromo 3-hexylthiophene and tris(4-bromophenyl)amine (or 1,3,5-tris(4-bromophenyl)benzene) monomers. Organic solvent-soluble polymers with number-average molecular weights of around 18,000 g mol−1 were obtained in 80–92% yields. The DSC and XRD results suggested that the branching structure hindered the stacking of polymer chains, leading to crystalline domains with less ordered packing in comparison with the linear analogous polymers. The results revealed that the hyperbranched polymer with triphenylbenzene as the branching unit exhibited a strong red-shift of the maximum absorption wavelength, attributed to a higher polymer stacking order as a result of the planar structure of triphenylbenzene.ConclusionBoth hyperbranched polymers with triphenylamine/triphenylbenzene as branching moieties exhibited high structural order in thin films, which can be promising for organic solar cell applications. The UV–vis absorption of the hyperbranched polymer containing triphenylbenzene as branching unit was red-shifted as compared with the triphenylamine-containing polymer, as a result of a higher chain packing degree.

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Section: Resultsmentioning

confidence: 99%

N-Benzoyl dithieno[3,2-b:2′,3′-d]pyrrole-based hyperbranched polymers by direct arylation polymerization

Nguyen

Tran

et al. 2017

Chemistry Central Journal

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“…3,3′′,4,4′′‐Tetrachloro‐5′‐(3,4‐dichlorophenyl)‐1,1′:3′,1′′‐terphenyl (2k): (Table ): White solid (167.60 mg, 98 %); 1 H NMR (500 MHz, CDCl 3 ): δ = 7.79 (s,3 H), 7.70 (d, J = 9.0 Hz, 3 H), 7.48 (t, J = 9.0 Hz, 3 H), 7.39 (t, J = 9.0 Hz, 3 H). 13 C NMR (125 MHz, CDCl 3 ): δ = 142.4, 141.2, 128.9, 127.6, 127.4, 125.2.…”

Section: Methodsmentioning

confidence: 99%

Facile Synthesis of 1,3,5‐Triarylbenzenes and 4‐Aryl‐NH‐1,2,3‐Triazoles Using Mesoporous Pd‐MCM‐41 as Reusable Catalyst

Saha

Peng

et al. 2018

Eur J Org Chem

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We report mesoporous nano‐Pd‐MCM‐41 catalyzed rapid and efficient synthesis of 1,3,5‐triarylbenzenes via de‐nitrative cyclotrimerization of β‐nitrostyrenes. All the reactions were very fast and high yielding. The Pd‐MCM‐41 was also very effective in catalyzing de‐nitrative [3+2] cycloaddition of β‐nitrostyrenes with TMSN3 to synthesize 4‐aryl‐NH‐1,2,3‐triazoles. The catalyst was reused at least up to eight times with minimum loss of catalytic activity.

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“…Although, previous reports stated that no reaction occurs with strong electron-withdrawing nitro group, the present system provided yield of 83% for the desired product aer 2.5 h (entry 3). 26,28 3.7. Recyclability of nanozeolite/HDTMA in the cyclotrimerization of acetophenone Capability of the catalyst to recycle was evaluated via cyclotrimerization of acetophenone as a typical reaction according to the common reaction procedure introduced in the Experimental section.…”

Section: Surface Modication Of Ncp By Some Quaternary Ammonium Salts...mentioning

confidence: 99%

A new method for the preparation of 1,3,5-triarylbenzenes catalyzed by nanoclinoptilolite/HDTMA

et al. 2015

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A new natural surface modified nanoclinoptilolite (NCP) was prepared and applied as an efficient catalyst for the cyclotrimerization of acetophenones to obtain 1,3,5-triarylbenzenes. The results showed that the efficiency of this catalytic system was enhanced due to the surface modification by hexadecyltrimethylammonium bromide (HDTMA-Br). This proposed protocol brings about significant economic and environmental advantages, such as operational simplicity, short reaction time, mild reaction conditions, good reaction yield, and high recyclability of the catalyst. Furthermore, the only side product of the reaction is water, which makes this methodology an environmentally friendly process.

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DBSA catalyzed cyclotrimerization of acetophenones: An efficient synthesis of 1,3,5-triarylbenzenes under solvent-free conditions

Cited by 24 publications

References 45 publications

N-Benzoyl dithieno[3,2-b:2′,3′-d]pyrrole-based hyperbranched polymers by direct arylation polymerization

N-Benzoyl dithieno[3,2-b:2′,3′-d]pyrrole-based hyperbranched polymers by direct arylation polymerization

Facile Synthesis of 1,3,5‐Triarylbenzenes and 4‐Aryl‐NH‐1,2,3‐Triazoles Using Mesoporous Pd‐MCM‐41 as Reusable Catalyst

A new method for the preparation of 1,3,5-triarylbenzenes catalyzed by nanoclinoptilolite/HDTMA

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