- Fluorescent hydrogel formation from carboxyphenyl-terpyridine
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We report the analysis of a novel terpyridine based supramolecular hydrogel which shows fluorescent properties in the gel but not in the sol form; the gel forms in a narrow pH range in aqueous solutions specifically in the presence of sodium ions, and con
- Griffith, Ashleigh,Bandy, Thomas J.,Light, Mark,Stulz, Eugen
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- Mitochondrial targeted osmium polypyridyl probe shows concentration dependent uptake, localisation and mechanism of cell death
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A symmetric osmium(ii) [bis-(4′-(4-carboxyphenyl)-2,2′:6′,2′′-terpyridine)] was prepared and conjugated to two mitochondrial-targeting peptide sequences; FrFKFrFK (r = d-arginine). The parent and conjugate complexes showed strong near infra-red emission c
- Gkika, Karmel Sofia,Byrne, Aisling,Keyes, Tia E.
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- Expanded ligands: Bis(2,2′:6′,2″-terpyridine carboxylic acid)ruthenium(ii) complexes as metallosupramolecular analogues of dicarboxylic acids
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Ligands in which multiple metal-binding domains are linked by a metal-containing moiety rather than a conventional organic group are described as "expanded ligands". The use of 4,4′-difunctionalised {Ru(tpy)2} units provides a linear spacer bet
- Constable, Edwin C.,Dunphy, Emma L.,Housecroft, Catherine E.,Neuburger, Markus,Schaffner, Silvia,Schaper, Frank,Batten, Stuart R.
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- Free radical oxidation reaction for selectively solvatochromic sensors with dynamic sensing ability
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A novel BODIPY (boradiazaindacene) dye denoted as BODIPY-DT containing terpyridine unit has been designed and characterized. The dye is found to be selective and visual solvatochromic sensor toward DMF among test organic solvents. The sensing process displays time-controllable, dynamic signal outputs in the emission colors including red, purple, yellow and even white emission colors. It is presented that selective free radical oxidation reaction happens during the recognition process.
- Shen, Fengjuan,Wang, Tao,Yu, Xudong,Li, Yajuan
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p. 1919 - 1922
(2019/12/27)
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- Postsynthetic modification of single Pd sites into uncoordinated polypyridine groups of a MOF as the highly efficient catalyst for Heck and Suzuki reactions
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A novel holmium(iii) metal-organic framework (Ho-MOF), namely, [Ho(2-TriPP-COO)3] (2) has been hydrothermally obtained using 4′-(4-carboxyphenyl)-2,2′:6′,2′′-terpyridine (2-TriPP-COOH) and Ho(NO3)3·5H2O, and it is structurally characterized by single-crystal XRD, powder XRD as well as elemental analysis. The postsynthetic modification of Ho-MOF is based on the utilization of a strong coordination effect between Pd2+ ions and free polypyridine groups in the skeleton of Ho-MOF, which play a critical role to access the highly efficient Pd-HoMOF catalyst. Also, Pd-HoMOF exhibits very high activity in Heck and Suzuki-Miyaura cross-coupling reactions. Moreover, the MOF catalyst displays good thermal stability (up to 400 °C), and it can be recovered and reused for five reaction cycles. The bridging between the MOF structure and homogeneous molecular Pd catalyst represents a good example in designing highly efficient catalysts for various fine chemical transformations.
- Dong, Dapeng,Li, Zhenghua,Liu, Dedi,Yu, Naisen,Zhao, Haiyan,Chen, Huiying,Liu, Jia,Liu, Dongping
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p. 9317 - 9323
(2018/06/08)
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- Synthesis and Biological Evaluation of Ru(II) and Pt(II) Complexes Bearing Carboxyl Groups as Potential Anticancer Targeted Drugs
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The synthesis and characterization of Pt(II) (1 and 2) and Ru(II) arene (3 and 4) or polypyridine (5 and 6) complexes is described. With the aim of having a functional group to form bioconjugates, one uncoordinated carboxyl group has been introduced in all complexes. Some of the complexes were selected for their potential in photodynamic therapy (PDT). The molecular structures of complexes 2 and 5, as well as that of the sodium salt of the 4′-(4-carboxyphenyl)-2,2′:6′,2″-terpyridine ligand (cptpy), were determined by X-ray diffraction. Different techniques were used to evaluate the binding capacity to model DNA molecules, and MTT cytotoxicity assays were performed against four cell lines. Compounds 3, 4, and 5 showed little tendency to bind to DNA and exhibited poor biological activity. Compound 2 behaves as bonded to DNA probably through a covalent interaction, although its cytotoxicity was very low. Compound 1 and possibly 6, both of which contain a cptpy ligand, were able to intercalate with DNA, but toxicity was not observed for 6. However, compound 1 was active in all cell lines tested. Clonogenic assays and apoptosis induction studies were also performed on the PC-3 line for 1. The photodynamic behavior for complexes 1, 5, and 6 indicated that their nuclease activity was enhanced after irradiation at = 447 nm. The cell viability was significantly reduced only in the case of 5. The different behavior in the absence or presence of light makes complex 5 a potential prodrug of interest in PDT. Molecular docking studies followed by molecular dynamics simulations for 1 and the counterpart without the carboxyl group confirmed the experimental data that pointed to an intercalation mechanism. The cytotoxicity of 1 and the potential of 5 in PDT make them good candidates for subsequent conjugation, through the carboxyl group, to "selected peptides" which could facilitate the selective vectorization of the complex toward receptors that are overexpressed in neoplastic cell lines.
- Martínez, Mángeles,Carranza, M. Pilar,Massaguer, Anna,Santos, Lucia,Organero, Juan A.,Aliende, Cristina,De Llorens, Rafael,Ng-Choi, Iteng,Feliu, Lidia,Planas, Marta,Rodríguez, Ana M.,Manzano, Blanca R.,Espino, Gustavo,Jalón, Félix A.
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p. 13679 - 13696
(2017/11/24)
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- Wirelike dinuclear ruthenium(II)polyterpyridine complexes based on D–P–A architecture: Experimental and theoretical investigation
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To accomplish the goal of prolonged excited state, efficient for interfacial electron injection and low electron-hole recombination (LUMO?→?HOMO of complex) we have synthesized a heteroleptic complexes 1 and 2 based on D–P–A architecture (where P?=?Photosensitizer, A?=?Acceptor and D?=?Donor). The complexes 1 and 2 show the average excited state lifetimes (τavg) of 25?ns and 12.67?ns respectively compared to 0.25?ns for [Ru(tpy)2]2PF6. The τavg of such an order is sufficient for performing the interfacial electron transfer into the conduction band of TiO2 and redox chemistry of excited state. The electrochemical studies exhibit the oxidation potential (Eox) of 1.23?V and 1.27?V vs SCE with associated excited-state redox potentials (Eox*=?0.95?V and ?0.85?V and Ered*=1.0?V and 0.88?V for complexes 1 and 2 respectively) have evidence for stronger reductant and oxidant behaviour in 1MLCT excited state. Subsequent interfacial study with TiO2 nanocrystal is in good agreement with photo induced electron injection from LUMO of complex to conduction band (CB) of TiO2 as LUMO level (?3.22?eV and 3.16?eV for complexes 1 and 2 respectively) of complexes is above the CB of TiO2 (?3.65?eV). The experimental photophysical results of both the complexes are well supported by time dependent density functional theory.
- Singh, Pallavi,Rana, Prem Jyoti Singh,Kar, Prasenjit
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p. 170 - 180
(2017/03/30)
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- Optical and electrochemical properties of covalent assembled bis(4′-carboxylic phenyl terpyridyl) Ru(II)-monolayer
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Homoleptic monomolecular layers of optically-rich and redox-active Ru(II)-4′carboxylic-phenyl-2,2′:6′,2″-terpyridyl (1) have been fabricated on SiOx-based substrates. The optical and redox properties of the films have been studied in detail. Th
- Mondal, Prakash Chandra
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supporting information
p. 7403 - 7408
(2015/09/02)
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- WAVELENGTH CONVERSION MATERIAL FOR HIGHLY EFFICIENT DYE-SENSITIZED SOLAR CELL, AND PREPARATION METHOD THEREOF
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Novel compounds represented by the present invention refers to formula 1 or formula 2, said novel compounds including wavelength change material, and including said wavelength change material relates to dye-sensitized solar cell.
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Paragraph 0268-0271
(2016/10/10)
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- Photoinduced electron transfer in a chromophore-catalyst assembly anchored to TiO2
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Photoinduced formation, separation, and buildup of multiple redox equivalents are an integral part of cycles for producing solar fuels in dye-sensitized photoelectrosynthesis cells (DSPECs). Excitation wavelength-dependent electron injection, intra-assembly electron transfer, and pH-dependent back electron transfer on TiO2 were investigated for the molecular assembly [((PO3H2-CH2)-bpy) 2Rua(bpy-NH-CO-trpy)Rub(bpy)(OH 2)]4+ ([TiO2-RuaII- RubII-OH2]4+; ((PO3H 2-CH2)2-bpy = ([2,2′-bipyridine]-4, 4′-diylbis(methylene))diphosphonic acid); bpy-ph-NH-CO-trpy = 4-([2,2′:6′,2″-terpyridin]-4′-yl)-N-((4′-methyl- [2,2′-bipyridin]-4-yl)methyl) benzamide); bpy = 2,2′-bipyridine). This assembly combines a light-harvesting chromophore and a water oxidation catalyst linked by a synthetically flexible saturated bridge designed to enable long-lived charge-separated states. Following excitation of the chromophore, rapid electron injection into TiO2 and intra-assembly electron transfer occur on the subnanosecond time scale followed by microsecond- millisecond back electron transfer from the semiconductor to the oxidized catalyst, [TiO2(e-)-RuaII-Ru bIII-OH2]4+→[TiO 2-RuaII-RubII-OH 2]4+.
- Ashford, Dennis L.,Song, Wenjing,Concepcion, Javier J.,Glasson, Christopher R. K.,Brennaman, M. Kyle,Norris, Michael R.,Fang, Zhen,Templeton, Joseph L.,Meyer, Thomas J.
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p. 19189 - 19198
(2013/01/15)
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- A simple and environmentally benign synthesis of polypyridine- polycarboxylic acids
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An oxidation method using dilute nitric acid solutions under solvothermal conditions has been developed to synthesise a series of polypyridine- polycarboxylic acids. It has been successfully applied to a range of methyl substituted polypyridines including symmetrical and asymmetrical 2,2′-bipyridines; 2,2′:6′,2″-terpyridines and; 2,2′:6′,2″:6″,2?-tetra-pyridines and yields crystalline polypyridine-polycarboxylic acids in a single step. Simple product recovery through filtration yields a recyclable filtrate. More forcing conditions led to demethylation of the polypyridine ligand most probably via decarboxylation. This simple approach avoids potentially harmful metal-based oxidants and negates any issues associated with the disposal of their resultant (hazardous) waste.
- Kelly, Niamh R.,Goetz, Sandrine,Hawes, Chris S.,Kruger, Paul E.
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scheme or table
p. 995 - 998
(2011/03/21)
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- Ruthenium(II) complexes of carboxylated terpyridines and dipyrazinylpyridines
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One-pot preparations of carboxylated 2,2′6′,2Prime;-terpyridine and 2,6-dipy:razin-2-ylpyridine ligands are reported, in free acid and ester forms, as well as their transformations to homoleptic RuII complexes in very good yields. Density functional theory calculations of their geometry-optimized structures enabled their comparison with crystal, structures; although the gross features of the crystal structures were reproduced, they showed much variability and distortion. The spectroscopic and electrochemical properties were analyzed from, the point of view of their geometry-optimized, structures, molecular orbital characteristics and electronic transitions, specifically to assess the effects of carboxylation and of inserting a phenylene spacer between the tridentate portion and the carboxyl group. The dipyrazinylpyridine complexes had HOMO levels stabilized by approximately 1 eV relative to the terpyridine analogues, and showed positive-shifted electrochemical potentials and redshifted electronic absorptions. Phenylene spacers were found to act as electron-donating groups, and the lowest-energy UV/Vis transitions showed intraligand character.
- Stublla, Arta,Potvin, Pierre G.
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experimental part
p. 3040 - 3050
(2011/01/10)
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- Concerted proton-electron transfer in a ruthenium terpyridyl-benzoate system with a large separation between the redox and basic sites
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(Figure Presented) To understand how the separation between the electron and proton-accepting sites affects proton-coupled electron transfer (PCET) reactivity, we have prepared ruthenium complexes with 4′-(4-carboxyphenyl) terpyridine ligands, and studied
- Manner, Virginia W.,Mayer, James M.
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supporting information; experimental part
p. 9874 - 9875
(2009/12/06)
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- Surface bottom-up fabrication of porphyrin-terminated metal complex molecular wires with photo-electron conversion properties on ITO
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We fabricated photoelectron conversion system with porphyrin-terminated "molecular wires" on an ITO surface synthesized using stepwise metal-terpyridine complexation reactions. The efficiency and the electrode potential singniflcantly depended on the meta
- Miyachi, Manko,Ohta, Makiko,Nakai, Misaki,Kubota, Yoshihiro,Yamanoi, Yoshinori,Yonezawa, Tetsu,Nishihara, Hiroshi
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p. 404 - 405
(2008/09/20)
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- New carboxy-functionalized terpyridines as precursors for zwitterionic ruthenium complexes for polymer-based solar cells
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New carboxy-terpyridines selectively functionalized at the 4-, 4′- and 4″-positions were prepared in a three-step procedure with good yields using the Kr?hnke reaction followed by saponification. Their complexation with ruthenium led to symmetric and unsy
- Duprez, Virginie,Krebs, Frederik C.
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p. 3785 - 3789
(2007/10/03)
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- PHARMACEUTICAL USE OF TERPYRIDINE DERIVATIVE
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A terpyridine derivative represented by general formula (I) (wherein R represents hydrogen, (un)substituted phenyl, pyridyl, etc.), which has the effect of promoting the production of nerve growth factors or a neurotrophic factor activity. Hence it can be
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