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Search Results (8)

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Keywords = oligopyridine

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24 pages, 10051 KiB  
Review
Functional Materials from Biomass-Derived Terpyridines: State of the Art and Few Possible Perspectives
by Jérôme Husson
Int. J. Mol. Sci. 2024, 25(16), 9126; https://doi.org/10.3390/ijms25169126 - 22 Aug 2024
Cited by 1 | Viewed by 1350
Abstract
This review focuses on functional materials that contain terpyridine (terpy) units, which can be synthesized from biomass-derived platform chemicals. The latter are obtained by the chemical conversion of raw biopolymers such as cellulose (e.g., 2-furaldehyde) or lignin (e.g., syringaldehyde). These biomass-derived platform chemicals [...] Read more.
This review focuses on functional materials that contain terpyridine (terpy) units, which can be synthesized from biomass-derived platform chemicals. The latter are obtained by the chemical conversion of raw biopolymers such as cellulose (e.g., 2-furaldehyde) or lignin (e.g., syringaldehyde). These biomass-derived platform chemicals serve as starting reagents for the preparation of many different terpyridine derivatives using various synthetic strategies (e.g., Kröhnke reaction, cross-coupling reactions). Chemical transformations of these terpyridines provide a broad range of different ligands with various functionalities to be used for the modification or construction of various materials. Either inorganic materials (such as oxides) or organic ones (such as polymers) can be combined with terpyridines to provide functional materials. Different strategies are presented for grafting terpy to materials, such as covalent grafting through a carboxylic acid or silanization. Furthermore, terpy can be used directly for the elaboration of functional materials via complexation with metals. The so-obtained functional materials find various applications, such as photovoltaic devices, heterogeneous catalysts, metal–organic frameworks (MOF), and metallopolymers. Finally, some possible developments are presented. Full article
(This article belongs to the Special Issue Biomass-Derived Materials: Synthesis and Applications)
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8 pages, 2129 KiB  
Short Note
Bis(2,6-di(pyridin-2-yl)pyridin-4-yl)-6,6′-(1,2-diselanediyl)dihexanoate
by Evelyn Popa, Adelina A. Andelescu, Valentin Badea, Paula Svera (m. Ianăşi) and Elisabeta I. Szerb
Molbank 2024, 2024(1), M1752; https://doi.org/10.3390/M1752 - 20 Dec 2023
Viewed by 2019
Abstract
The present paper describes the preparation and characterization of a new dinuclear ligand based on terpyridine featuring a diselenide unit. This new compound was synthesized in a two-step procedure that first involved the insertion of the diselenide moiety on a carboxylic acid and [...] Read more.
The present paper describes the preparation and characterization of a new dinuclear ligand based on terpyridine featuring a diselenide unit. This new compound was synthesized in a two-step procedure that first involved the insertion of the diselenide moiety on a carboxylic acid and was followed by a Steglich esterification reaction between the biscarboxylic acid containing the diselenide unit and 2,6-di(pyridin-2-yl)pyridin-4-ol (tpyOH). The title compound was characterized via FT-IR, Raman, NMR (1D and 2D), and UV-Vis spectroscopies and elemental analysis. Emission properties were investigated. Full article
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15 pages, 3074 KiB  
Article
Current Design of Mixed-Ligand Complexes of Magnesium(II): Synthesis, Crystal Structure, Thermal Properties and Biological Activity against Mycolicibacterium Smegmatis and Bacillus Kochii
by Marina E. Nikiforova, Dmitriy S. Yambulatov, Yulia V. Nelyubina, Petr V. Primakov, Olga B. Bekker, Konstantin B. Majorov, Maxim A. Shmelev, Andrey V. Khoroshilov, Igor L. Eremenko and Irina A. Lutsenko
Crystals 2023, 13(9), 1306; https://doi.org/10.3390/cryst13091306 - 27 Aug 2023
Cited by 3 | Viewed by 2401
Abstract
The interaction of Mg2+ with 2-furoic acid (HFur) and oligopyridines, depending on the synthesis conditions, leads to the formation of mixed-ligand complexes [Mg(H2O)4(phen)]·2HFur·phen·H2O (1), [Mg(NO3)2(phen)2] (2) [...] Read more.
The interaction of Mg2+ with 2-furoic acid (HFur) and oligopyridines, depending on the synthesis conditions, leads to the formation of mixed-ligand complexes [Mg(H2O)4(phen)]·2HFur·phen·H2O (1), [Mg(NO3)2(phen)2] (2) and [Mg3(Fur)6(bpy)2]·3CH3CN (3); these structures were determined with an SC X-ray analysis. According to the X-ray diffraction data, in complex 1, obtained in ambient conditions, the magnesium cation coordinated four water molecules and one phenanthroline fragment, while in complexes 2 and 3 (synthesized in an inert atmosphere), the ligand environment of the complexing agent was represented by neutral oligopyridine molecules and acid anions. The thermal behavior of 1 and 2 was studied using a simultaneous thermal analysis (STA). The in vitro biological activity of complexes 1–3 was studied in relation to the non-pathogenic Mycolicibacterium smegmatis and the virulent strain Mycobacterium tuberculosis H37Rv. Full article
(This article belongs to the Special Issue Feature Papers in Crystals 2023)
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4 pages, 788 KiB  
Short Note
4′-(N-(2-Cyanoethyl)pyrrol-2-yl)-2,2′:6′,2″-terpyridine
by Jérôme Husson
Molbank 2023, 2023(3), M1689; https://doi.org/10.3390/M1689 - 5 Jul 2023
Cited by 1 | Viewed by 1434
Abstract
The preparation and characterization of a new multi-functionalized terpyridine molecule featuring a pyrrole heterocycle and a cyano group is described. This new compound was obtained via a KF/alumina-catalyzed Michael addition of 4′-(pyrrol-2-yl)-2,2′:6′,2″-terpyridine into acrylonitrile. The mild reaction conditions leave the nitrile group unaltered. [...] Read more.
The preparation and characterization of a new multi-functionalized terpyridine molecule featuring a pyrrole heterocycle and a cyano group is described. This new compound was obtained via a KF/alumina-catalyzed Michael addition of 4′-(pyrrol-2-yl)-2,2′:6′,2″-terpyridine into acrylonitrile. The mild reaction conditions leave the nitrile group unaltered. The title compound was fully characterized via NMR spectroscopy (1H and 13C) as well as via high resolution mass spectrometry and infrared spectroscopy. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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5 pages, 825 KiB  
Short Note
4′-(3,5-Dimethoxy-4-propargyloxyphenyl)-2,2′:6′,2″-terpyridine
by Romain Chameroy, Clément Deboskre, Jérôme Husson, Isabelle Jourdain and Michael Knorr
Molbank 2022, 2022(4), M1527; https://doi.org/10.3390/M1527 - 14 Dec 2022
Viewed by 1749
Abstract
The preparation and characterization of a new terpyridine molecule containing an acetylenic moiety is described. Part of this molecule, unknown in the literature, is obtained from a biomass-derived synthon that is formed from the naturally occurring syringaldehyde 4-hydroxy-3,5-dimethoxybenzaldehyde. The title compound was fully [...] Read more.
The preparation and characterization of a new terpyridine molecule containing an acetylenic moiety is described. Part of this molecule, unknown in the literature, is obtained from a biomass-derived synthon that is formed from the naturally occurring syringaldehyde 4-hydroxy-3,5-dimethoxybenzaldehyde. The title compound was fully characterized by NMR spectroscopy (1H and 13C), as well as by high-resolution mass spectrometry and infrared spectroscopy. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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7 pages, 1539 KiB  
Proceeding Paper
New 2,6-Bis(5-phenyloxazolyl)pyridine Ligands for Luminescent LnIII Complexes
by André Carvalho, Paula M. T. Ferreira and José A. Martins
Chem. Proc. 2022, 12(1), 56; https://doi.org/10.3390/ecsoc-26-13714 - 18 Nov 2022
Viewed by 1756
Abstract
Lanthanide (Ln(III)) luminescent complexes have been attracting interest for technological applications and molecular imaging. The luminescence of Ln(III)) ions is weak and depends on the use of light absorbing coordination ligands which sensitizes the lanthanide ion. A large variety of coordination ligands has [...] Read more.
Lanthanide (Ln(III)) luminescent complexes have been attracting interest for technological applications and molecular imaging. The luminescence of Ln(III)) ions is weak and depends on the use of light absorbing coordination ligands which sensitizes the lanthanide ion. A large variety of coordination ligands has been screened such as dipicolinates, oligo-pyridines, cyclen and crown ether derivatives, porphyrins, cryptands or calixarenes. In our research group we have developed an expeditious methodology to prepare bis(oxazolyl)pyridine ligands for LnIII from threonine and 2,6-pyridinedicarbonyl dichloride. In this work, two new pyridine-bis-oxazolyl ligands with an aromatic ring in position 5 of the oxazole ring were prepared from phenyl-serine and 2,6-pyridinedicarbonyl dichloride. The photophysical properties of compounds 1 and 2 were studied in acetonitrile and in Tris-HCl buffer (0.1 M, pH 7.1). These compounds were used for complexation with Eu(III) and/or Tb(III) ions and the photophysical properties of the complexes studied. Luminescence titrations with anhydrous EuCl3 and TbCl3 allowed the determination of the stoichiometry of the complexes and of the stability constants. Full article
(This article belongs to the Proceedings of The 26th International Electronic Conference on Synthetic Organic Chemistry)
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5 pages, 1342 KiB  
Short Note
4′-(N-(Propargyl)pyrrol-2-yl)-2,2′:6′,2′′-terpyridine
by Jérôme Husson and Laurent Guyard
Molbank 2022, 2022(2), M1356; https://doi.org/10.3390/M1356 - 25 Mar 2022
Cited by 2 | Viewed by 2811
Abstract
A new terpyridine molecule, bearing a N-propargylated pyrrole, was prepared and characterized. Its synthesis was based on a Krohnke-type reaction between 2-acetylpyridine and N-propargylpyrrole-2-carboxaldehyde in a basic medium. An allene-containing terpyridine was also obtained as a by-product. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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4 pages, 704 KiB  
Communication
4′-(5-Methylfuran-2-yl)-2,2′:6′,2″-terpyridine: A New Ligand Obtained from a Biomass-Derived Aldehyde with Potential Application in Metal-Catalyzed Reactions
by Jérôme Husson and Laurent Guyard
Molbank 2018, 2018(4), M1032; https://doi.org/10.3390/M1032 - 24 Nov 2018
Cited by 8 | Viewed by 2965
Abstract
The new ligand 4′-(5-methylfuran-2-yl)-2,2′:6′,2″-terpyridine (1) was prepared in one step from 2-acetylpyridine and 5-methylfurfural. The latter is an aldehyde that can be readily obtained from biomass. The new terpyridine molecule was characterized by 1H and 13C-NMR spectroscopy as well [...] Read more.
The new ligand 4′-(5-methylfuran-2-yl)-2,2′:6′,2″-terpyridine (1) was prepared in one step from 2-acetylpyridine and 5-methylfurfural. The latter is an aldehyde that can be readily obtained from biomass. The new terpyridine molecule was characterized by 1H and 13C-NMR spectroscopy as well as by elemental analyses and HR-MS. Owing to its chelating properties, this new terpyridine molecule was tested as a ligand in a metal-catalyzed reaction: The Ni-catalyzed dimerization of benzyl bromide. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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