14162-95-9Relevant articles and documents
A high molar extinction coefficient mono-anthracenyl bipyridyl heteroleptic ruthenium(II) complex: Synthesis, photophysical and electrochemical properties
Adeloye, Adewale O.,Ajibade, Peter A.
, p. 4615 - 4631 (2011)
In our quest to develop good materials as photosensitizers for photovoltaic dye-sensitized solar cells (DSSCs), cis-dithiocyanato-4-(2,3-dimethylacrylic acid)-2,2'- bipyridyl-4-(9-anthracenyl-(2,3-dimethylacrylic)-2,2'-bipyridyl ruthenium(II) complex, a high molar extinction coefficient charge transfer sensitizer, was designed, synthesized and characterized by spectroscopy and electrochemical techniques. Earlier studies on heteroleptic ruthenium(II) complex analogues containing functionalized oligo-anthracenyl phenanthroline ligands have been reported and documented. Based on a general linear correlation between increase in the length of p-conjugation bond and the molar extinction coefficients, herein, we report the photophysical and electrochemical properties of a Ru(II) bipyridyl complex analogue with a single functionalized anthracenyl unit. Interestingly, the complex shows better broad and intense metal-to ligand charge transfer (MLCT) band absorption with higher molar extinction coefficient (δmax = 518 nm, σ = 44900 M-1cm-1), and appreciable photoluminescence spanning the visible region than those containing higher anthracenyl units. It was shown that molar absorption coefficient of the complexes may not be solely depended on the extended p-conjugation but are reduced by molecular aggregation in the molecules.
Synthesis and characterization of a new ditopic bipyridine-terpyridine bridging ligand using a Suzuki cross-coupling reaction
Zibaseresht, Ramin
, p. 277 - 287 (2019)
Synthesis of a new bridging ligand 4'-{4-[(2,2'-bipyridin)-4-yl]-phenyl}-2,2':6'-2''-terpyridine (I) was reported. A Suzuki cross-coupling reaction was conducted for the preparation of such ligand in two different routes either between 4'-(4-bromophenyl)-2,2':6'-2''-terpyridine and 2,2'-bipyridyl-4-boronic acid or 4'-(4-boronatophenyl)-2,2':6',2''-terpyridine and 4-bromo-2,2'-bipyridine. Br HO OH B + N N N N N N N HO OH B Br N + N N N (I) N N N N
Synthesis and spectral properties of ruthenium(II) complexes based on 2,2′-bipyridines modified by a perylene chromophore
Kodama, Koichi,Kobayashi, Akinori,Hirose, Takuji
, p. 5514 - 5517 (2013)
Five new 2,2′-bipyridines functionalized with a perylene or a perylenediimide moiety were synthesized and the corresponding heteroleptic ruthenium(II) complexes ([Ru(bpy)2(L)](PF6)2; bpy = 2,2′-bipyridyl, L = perylene-substituted bpy ligand) were prepared. The UV-vis spectra of the ruthenium(II) complexes showed red-shifted and intense absorption bands derived from the conjugated structure of the new ligands.
Synthesis and optical properties of bifunctional thiophene molecules coordinated to ruthenium
Bair, Joseph S.,Harrison, Roger G.
, p. 6653 - 6661 (2007)
(Chemical Equation Presented) A series of unsymmetrical bi- and tetrathiophenes have been synthesized with bipyridine and phosphonic acid functional groups. To do this, phosphonic esters were bonded to thiophenes and the thiophenes coupled to bipyridine. After synthesis of the thienylbipyridines, bis(bipyridine) ruthenium was coordinated to them through the bipyridines. The thienylbipyridines absorb visible light and fluoresce; however, on attachment to ruthenium, both their fluorescence and that of ruthenium are quenched. An additional effect of coordinating ruthenium to the thiophenes is a new absorption band around 470 nm. Variation in oligothiophene length and bipyridine substitution position allowed comparison of the effect of these variables on electronic properties. The longer oligothiophenes display lower-energy absorptions and emissions than that of the shorter thiophenes. In contrast, the position of the bipyridine attachment does not have a large effect on the absorbance or emission wavelength, or on the fluorescence quantum yield.
Stereoselective and hierarchical self-assembly from nanotubular homochiral helical coordination polymers to supramolecular gels
He, Yabing,Bian, Zheng,Kang, Chuanqing,Gao, Lianxun
, p. 5695 - 5697 (2010)
A new binaphthylbisbipyridine-based ligand underwent diastereoselective self-assembly with silver(i) ions to form nanotubular homochiral helical coordination polymers, which further hierarchically self-assemble into nanofibers, capable of immobilizing organic solvents.
Microwave assisted synthesis of 3-(2,2′-bipyridine-4-yl)-2-propenoic acid ethyl ester
Heintz, Katharina,Imhof, Wolfgang,G?rls, Helmar
, p. 991 - 998 (2017)
Abstract: 3-(2,2′-Bipyridine-4-yl)-2-propenoic acid ethyl ester which may be used for the introduction of metal coordination sites in polyacrylates is synthesized by an improved synthetic route to the key intermediate 4-bromo-2,2′-bipyridine working under microwave conditions, which leads to drastic shortening of reaction times, as well as to the reduction of reaction steps. In addition, a synthetic procedure to formyl-bipyridines that is not based on reductive or oxidative reaction conditions could be applied. Starting from the formyl-bipyridine derivative the title compound may be effectively generated using modified Horner–Wadsworth–Emmons reaction conditions to yield the new ligand. Graphical abstract: [Figure not available: see fulltext.].
Click chemistry on a ruthenium polypyridine complex. An efficient and versatile synthetic route for the synthesis of photoactive modular assemblies
Baron, Aurelie,Herrero, Christian,Quaranta, Annamaria,Charlot, Marie-France,Leibl, Winfried,Vauzeilles, Boris,Aukauloo, Ally
, p. 5985 - 5987 (2012)
In this Communication, we present the synthesis and use of [Ru(bpy) 2(bpy-CCH)]2+, a versatile synthon for the construction of more sophisticated dyads by means of click chemistry. The resulting chromophore-acceptor or -donor complexes have been studied by flash photolysis and are shown to undergo efficient electron transfer to/from the chromophore. Additionally, the photophysical and chemical properties of the original chromophore remain intact, making it a very useful component for the preparation of visible-light-active dyads.
A boronic acid-diol interaction is useful for chiroselective transcription of the sugar structure to the Δ- Versus Λ-[CoIII(bpy)3]3+ ratio
Mizuno, Toshihisa,Takeuchi, Masayuki,Hamachi, Itaru,Nakashima, Kazuaki,Shinkai, Seiji
, p. 2281 - 2288 (1998)
In order to apply boronic acid-saccharide interactions to the chiroselective synthesis of Δ- and Λ-[CoIII(bpy)3]3+ saccharide-binding ligands, 2,2′-bipyridine-4-boronic acid (bpymb) and 2,2′-bipyridine-4,4′-diboronic acid (bpydb) were newly synthesized. It was shown that most D-saccharides form cyclic 1:1 complexes with bpydb to afford the CD-active species. The positive exciton coupling band implies that two pyridine rings are twisted in a clockwise direction ((R)-chirality). In contrast, such a CD-active species was not yielded from bpymb. The treatment of the bpydb-D-saccharide complexes with Co(OAc)2 gave the substitution-active [CoII(bpyba)3]4--saccharide complexes, which were oxidized to the substitution-inactive [CoIII(bpyba)3]3--saccharide complexes. In this stage, the Δ vs. Λ ratio was fixed. The complexes were converted to [CoIII(bpy)]3+ by treatment with AgNO3 and the e.e. was determined by comparison with authentic Δ- or Λ-[CoIII(bpy)]3+. The Δ-isomer was obtained in excess from most D-saccharides but the Λ-isomer was also obtained from D-fructose and D-fucose. At 4°C, the largest e.e. for bpydb was attained with D-glucose (47% e.e.; Δ excess). Under the same reaction conditions the bpymb + D-glucose system gave 16% e.e. (Δ excess). The e.e. of the bpydb + D-glucose system increased with lowering the reaction temperature and at -25°C it reached 79% e.e. The foregoing results clearly establish that the saccharide-templated synthesis is useful as a new concept for the preparation of chiral tris(2,2′-bipyridine)-metal complexes. Furthermore, the Δ vs. Λ equilibrium can be shifted in either direction by the selection of saccharide enantiomers.
Conducting redox polymers: Investigations of polythiophene-Ru(bpy)3(n+) hybrid materials
Zhu, Sherry S.,Kingsborough, Richard P.,Swager, Timothy M.
, p. 2123 - 2131 (1999)
A series of thiophene-appended Ru(II)(bpy)3 derivatives, Ru(1)3, Ru(2)3, Ru(3)3, Ru(bpy)2(1), and Ru(bpy)2(2), and their resulting polymers have been synthesized and characterized. The bpy ligands 5,5'-bis (5-(2,2'-bithienyl))-2,2'-bipyridine, 1, 4,4'-bis (5-(2,2'-bithienyl))-2,2'- bipyridine, 2, and 4-(5-(2,2'-bithienyl))-2,2'-bipyridine, 3, all contain electrochemically polymerizable bithienyl moieties. The monomers Ru (2)3, Ru(3)3, Ru (bpy)2(1) and Ru(bpy)2(2) display spectroscopic features that are similar to the ligand-based and MLCT bands found for Ru(bpy)3. The cyclic voltammograms of all of these polymers display both metal-centered and thiophene-based electroactivity. High redox conductivity was found in poly(Ru(2)3) and poly(Ru(3)3) for both the thiophene-based oxidation and metal-based reduction processes. These results indicate that the polymers display charge localization for both the metal complexes as well as the tetrathienyl connecting units. The degree of interconnection (number of linkages) as well as the substitution pattern were found to control the conductivity of these polymers. The highest conductivity (3.3 x 10-3 S cm- 1) was found for poly(Ru(2)3), which is able to have up to 6 linkages with other ruthenium complexes as well as possessing a 4,4'-substitution pattern that allows effective orbital overlap of the conjugated polymer backbone with the ruthenium centers.
Sensitizer-catalyst assemblies for water oxidation
Wang, Lei,Mirmohades, Mohammad,Brown, Allison,Duan, Lele,Li, Fusheng,Daniel, Quentin,Lomoth, Reiner,Sun, Licheng,Hammarstr?m, Leif
, p. 2742 - 2751 (2015)
Two molecular assemblies with one Ru(II)-polypyridine photosensitizer covalently linked to one Ru(II)(bda)L2 catalyst (1) (bda = 2,2′-bipyridine-6,6′-dicarboxylate) and two photosensitizers covalently linked to one catalyst (2) have been prepared using a simple C-C bond as the linkage. In the presence of sodium persulfate as a sacrificial electron acceptor, both of them show high activity for catalytic water oxidation driven by visible light, with a turnover number up to 200 for 2. The linked photocatalysts show a lower initial yield for light driven oxygen evolution but a much better photostability compared to the three component system with separate sensitizer, catalyst and acceptor, leading to a much greater turnover number. Photocatalytic experiments and time-resolved spectroscopy were carried out to probe the mechanism of this catalysis. The linked catalyst in its Ru(II) state rapidly quenches the sensitizer, predominantly by energy transfer. However, a higher stability under photocatalytic condition is shown for the linked sensitizer compared to the three component system, which is attributed to kinetic stabilization by rapid photosensitizer regeneration. Strategies for employment of the sensitizer-catalyst molecules in more efficient photocatalytic systems are discussed.
