Water based surfactant-assisted synthesis of thienylpyridines and thienylbipyridine intermediates

Published on Feb 1, 2017in Dyes and Pigments4.889
· DOI :10.1016/J.DYEPIG.2016.10.031
Pierluigi Quagliotto28
Estimated H-index: 28
(UNITO: University of Turin),
Nadia Barbero25
Estimated H-index: 25
(UNITO: University of Turin)
+ 4 AuthorsGuido Viscardi34
Estimated H-index: 34
(UNITO: University of Turin)
Sources
Abstract
Abstract The connection between heterocyclic systems by forming new C C bond is a relevant topic for the easy preparation of intermediates and functional dyes for technological applications. Several methods were developed in the last decades and the urge for sustainable synthetic chemical methods pushed us to prepare thienylpyridines and two thienylbipyridine ligands by the Suzuki reaction in aqueous CTAB micellar medium and in presence of a Pd catalyst. These intermediates can be found as component of dyes and functional thiophene monomers. Reaction conditions were optimized under both thermal and microwave (MW) activation obtaining good yields (70–93%) using Pd(PPh3)4 as catalyst. Two thienylbipyridine ligands were prepared and the transformation of one of them into a terthiophene-based bipyridine ligand was easily obtained by almost green methods and with very good yield. This clean and sustainable method can be proposed as a green step to obtain intermediates and final dyes for technological applications, such as CO2 reduction, in gram-multigram scale.
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#2Simona Prosperini (UNITO: University of Turin)H-Index: 2
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Three novel thiophene substituted bipyridine ligands and their corresponding rhenium complexes were synthesized and tested for the electrocatalytic reduction of CO2. Two complexes underwent oxidative electropolymerization on a glassy carbon electrode (GCE) surface. The conductive polymers chemically deposited on the GCE allow electron transport from the surface to the polymer-attached rhenium catalytic center in contact with the solution. The chemically modified electrodes show significant catal...
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#1Francesca Baldassarre (University of Salento)H-Index: 11
#2Federica Foglietta (UNITO: University of Turin)H-Index: 14
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The photodynamic activity occurring through the lysosome photo-damage is effective in terms of triggered synergic effects which can avoid chemo-resistance pathways. The potential photodynamic activity of two fluorescent lysosome-specific probes was studied providing their interaction with human serum albumin, demonstrating their in vitro generation of singlet oxygen and investigating the resulted photo-toxic effect in human cancer cells.
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#1Davide Saccone (UNITO: University of Turin)H-Index: 8
#2Claudio Magistris (UNITO: University of Turin)H-Index: 11
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Terpyridine and quaterpyridine-based complexes allow wide light harvesting of the solar spectrum. Terpyridines, with respect to bipyridines, allow for achieving metal-complexes with lower band gaps in the metal-to-ligand transition (MLCT), thus providing a better absorption at lower energy wavelengths resulting in an enhancement of the solar light-harvesting ability. Despite the wider absorption of the first tricarboxylate terpyridyl ligand-based complex, Black Dye (BD), dye-sensitized solar cel...
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#1Denis PratH-Index: 3
#2Andy WellsH-Index: 4
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A selection guide of common solvents has been elaborated, based on a survey of publically available solvent selection guides. In order to rank less classical solvents, a set of Safety, Health and Environment criteria is proposed, aligned with the Global Harmonized System (GHS) and European regulations. A methodology based on a simple combination of these criteria gives an overall preliminary ranking of any solvent. This enables in particular a simplified greenness evaluation of bio-derived solve...
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#1Alessandro Dani (UNITO: University of Turin)H-Index: 8
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A series of porous poly(ionic liquid)s (PILs) were synthesized using an innovative method which involves the synthesis of non-ionic co-polymers such as divinylbenzene and vinylimidazole, followed by an alkylation step to introduce the ionic liquid functionality in the polymeric matrix. This synthetic strategy allowed us to obtain tunable imidazolium type PILs having simultaneously high surface area and exposed ionic moieties. A set of PILs was obtained by changing systematically the alkyl chains...
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#1Yinjun Zou (NTU: Nanyang Technological University)H-Index: 3
#2Guizhou Yue (Sichuan Agricultural University)H-Index: 15
Last. Jianrong Steve Zhou (NTU: Nanyang Technological University)H-Index: 23
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A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids.
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#1Wouter Dierckx (University of Hasselt)H-Index: 6
#2Wibren D. Oosterbaan (University of Hasselt)H-Index: 18
Last. Jean Manca (University of Hasselt)H-Index: 56
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Semiconducting poly(3-alkylthiophene) nanofibers show remarkable optical and electrical properties, and because of their high aspect ratios they are perfectly suited to serve as organic quasi one-dimensional charge carriers. Hence, they offer interesting perspectives for next generation printable optoelectronic applications. This feature article provides an overview of the current state of the art regarding the preparation and characterization of poly(3-alkylthiophene) nanofibers, and a discussi...
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#6Hua Chen (Sichuan University)H-Index: 10
A new simple Pd(memantine) 2 Cl 2 complex was synthesized and characterized by 1 H NMR, 13 C NMR and X-ray single crystal structure determination. The Suzuki–Miyaura reaction of aryl bromides catalyzed by Pd(memantine) 2 Cl 2 complex was investigated in air with different temperature. The high turnover numbers of 650,000 have been obtained in the reaction of 4-bromonitrobenzene with phenylboronic acid at 80 °C. At room temperature, the complex also showed high activity for Suzuki–Miyaura cross-c...
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The catalytic hydrolysis of bis(4-nitrophenyl)phosphate (BNPP) and bis(2,4-dinitrophenyl)phosphate (BDNPP) catalyzed by α-nucleophiles in gemini micellar media was investigated at 27 °C. The cationic gemini surfactants, i.e., alkanediyl-α-ω-bis(hydroxyethylmethylhexadecylammonium bromide) (16-s-16 MEA 2Br−, where s = 4 and 6) were used. Nucleophilic reactivity of α-nucleophiles such as hydroperoxide (HOO−), acetohydroxamate (AHA−), and butane 2,3-dione monoximate ions (BDMO−) were compared. The ...
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Abstract The monodisperse palladium nanoparticles with the size of about 5.0 nm were prepared by the thermal decomposition of palladium acetylacetonate in the presence of oleylamine and borane tributylamine complex. The palladium nanoparticles were loaded on the active carbon black by the sonication followed by the acetic acid cleaning, and then they are used as the nanocatalysts for carbon coupling reactions, such as Heck reactions and Suzuki reactions. The nanocatalysts can promote Heck reacti...
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Certainly, the success of polythiophenes is due in the first place to their outstanding electronic properties and superior processability. Nevertheless, there are additional reasons that contribute to arouse the scientific interest around these materials. Among these, the large variety of chemical modifications that is possible to perform on the thiophene ring is a precious aspect. In particular, a turning point was marked by the diffusion of synthetic strategies for the preparation of terthioph...
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#1Fabrizio SordelloH-Index: 17
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According to numerous previous reports, a Z-scheme with two photon absorbers is the most promising strategy to achieve artificial photosynthesis, but in addition to two efficient catalysts—one for oxygen evolution, the other for CO2 reduction—two different and complementary semiconducting sensitizers are required. Here we present the synthesis of two bipyridine-functionalized terthiophenes, which can be electropolymerized to give photoactive p-type semiconductors the capability to perform as pho...
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Microwave-assisted organic synthesis (MAOS) provides a novel and efficient means of achieving heat organic reactions. Nevertheless, the potential arcing phenomena via microwave (MW) interaction with solid metal catalysts has limited its use by organic chemists. As arcing phenomena are now better understood, new applications of Pd/C-catalyzed reactions under MW dielectric heating are now possible. In this review, the state of the art, benefits, and challenges of coupling MW heating with heterogen...
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