6813-38-3Relevant articles and documents
Synthesis and characterization of cross-linkable ruthenium complex dye and its application on dye-sensitized solar cells
Liu, Ken-Yen,Hsu, Chiao-Ling,Chang, Shun-Hsing,Chen, Jian-Ging,Ho, Kuo-Chuan,Lin, King-Fu
, p. 366 - 372 (2010)
A new crosslinkable light sensitizer, Ru(2,2′-bipyridine- 4,40-bicarboxylic acid)(4,4′-bis(11-dodecenyl)-2,2′-bipyridine)( NCS)2, denoted as Ru-C for titanium oxide nanocrystallinebased solar cells was synthesized with its crosslinking properties invesitigated by Fourier-transform infrared and UV-vis absorption spectroscopies. After crosslinking by itself or copolymerizing with methyacrylic acid, their sensitized solar cells with poly(methylacrylate)-gelled electrolyte system not only attained more than 5% of power conversion efficiency at AM 1.5 illumination (100 mW/cm2), but also gave rise to long storage life. To the best our knowledge, this is the first crosslinkable dye ever applied to the DSSC in the literature.
Hexameric supramolecular scaffold orients carbohydrates to sense bacteria
Gruenstein, Dan,Maglinao, Maha,Kikkeri, Raghavendra,Collot, Mayeul,Barylyuk, Konstantin,Lepenies, Bernd,Kamena, Faustin,Zenobi, Renato,Seeberger, Peter H.
, p. 13957 - 13966 (2011)
Carbohydrates are integral to biological signaling networks and cell-cell interactions, yet the detection of discrete carbohydrate-lectin interactions remains difficult since binding is generally weak. A strategy to overcome this problem is to create multivalent sensors, where the avidity rather than the affinity of the interaction is important. Here we describe the development of a series of multivalent sensors that self-assemble via hydrophobic supramolecular interactions. The multivalent sensors are comprised of a fluorescent ruthenium(II) core surrounded by a heptamannosylated β-cyclodextrin scaffold. Two additional series of complexes were synthesized as proof-of-principle for supramolecular self-assembly, the fluorescent core alone and the core plus β-cyclodextrin. Spectroscopic analyses confirmed that the three mannosylated sensors displayed 14, 28, and 42 sugar units, respectively. Each complex adopted original and unique spatial arrangements. The sensors were used to investigate the influence of carbohydrate spatial arrangement and clustering on the mechanistic and qualitative properties of lectin binding. Simple visualization of binding between a fluorescent, multivalent mannose complex and the Escherichia coli strain ORN178 that possesses mannose-specific receptor sites illustrates the potential for these complexes as biosensors.
Synthesis and recognition behaviour of allosteric hemicarcerands
Lützen, Arne,Ha?, Oliver,Bruhn, Torsten
, p. 1807 - 1811 (2002)
Bipyridine bridged bis(resorcinarenes) have been prepared. Upon co-ordinating to a transition metal ion, e.g. Ag+, the respective metal complex forms a hemicarcerand-like structure with the two resorcinarene moieties capable of binding non-polar organic molecules in a co-operative fashion, as shown qualitatively by NMR spectroscopy.
Protein Surface Mimetics: Understanding How Ruthenium Tris(Bipyridines) Interact with Proteins
Hewitt, Sarah H.,Filby, Maria H.,Hayes, Ed,Kuhn, Lars T.,Kalverda, Arnout P.,Webb, Michael E.,Wilson, Andrew J.
, p. 223 - 231 (2017)
Protein surface mimetics achieve high-affinity binding by exploiting a scaffold to project binding groups over a large area of solvent-exposed protein surface to make multiple cooperative noncovalent interactions. Such recognition is a prerequisite for competitive/orthosteric inhibition of protein–protein interactions (PPIs). This paper describes biophysical and structural studies on ruthenium(II) tris(bipyridine) surface mimetics that recognize cytochrome (cyt) c and inhibit the cyt c/cyt c peroxidase (CCP) PPI. Binding is electrostatically driven, with enhanced affinity achieved through enthalpic contributions thought to arise from the ability of the surface mimetics to make a greater number of noncovalent interactions than CCP with surface-exposed basic residues on cyt c. High-field natural abundance 1H,15N HSQC NMR experiments are consistent with surface mimetics binding to cyt c in similar manner to CCP. This provides a framework for understanding recognition of proteins by supramolecular receptors and informing the design of ligands superior to the protein partners upon which they are inspired.
Evaluation of Tris-Bipyridine Chromium Complexes for Flow Battery Applications: Impact of Bipyridine Ligand Structure on Solubility and Electrochemistry
Cabrera, Pablo J.,Yang, Xingyi,Suttil, James A.,Brooner, Rachel E. M.,Thompson, Levi T.,Sanford, Melanie S.
, p. 10214 - 10223 (2015)
This report describes the design, synthesis, solubility, and electrochemistry of a series of tris-bipyridine chromium complexes that exhibit up to six reversible redox couples as well as solubilities approaching 1 M in acetonitrile. We have systematically modified both the ligand structure and the oxidation state of these complexes to gain insights into the factors that impact solubility and electrochemistry. The results provide a set of structure-solubility-electrochemistry relationships to guide the future development of electrolytes for nonaqueous flow batteries. In addition, we have identified a promising candidate from the series of chromium complexes for further electrochemical and battery assessment.
Probing the limits: Ultraslow diffusion and heterogeneous electron transfers in redox polyether hybrid cobalt bipyridine molten salts
Crooker, Joseph C.,Murray, Royce W.
, p. 3245 - 3252 (2000)
This paper describes microelectrode voltammetry measurements of self-diffusion coefficients and of heterogeneous Co(II/III) electron-transfer rate constants (k°) in undiluted molten salts of three cobalt tris(bipyridine) perchlorate complexes in which the bipyridine ligands are "tailed" with poly(propylene oxide) and poly(ethylene oxide) oligomers. The self-diffusion coefficients are measured with potential step chronoamperometry and range from 10-12 to 10-17 cm2/s, while the quasi-reversible reaction rate constants are measured using cyclic voltammetry and small potential steps and range from 10-7 to 10-12 cm/s. The k° measurements are unusual in that when rate constants become smaller, the reaction remains quasi-reversible, because of concurrently decreasing self-diffusion rates. The measurements are, furthermore, accomplished in the face of uncompensated resistances that range from mega- to gigaohms, which is made possible by the combination of microelectrode properties and small diffusivities. The melt in which self-diffusion and k° values are smallest is at a temperature below its nominal glassing transition and in the regime of molecule-scale diffusion profiles.
An efficient preparation of 4,4'-dicarboxy-2,2'-bipyridine
Oki,Morgan
, p. 4093 - 4097 (1995)
A convenient and high yield preparation of 4,4'-dicarboxy-2,2'-bipyridine from the oxidation 4,4'-dimethyl-2,2'-bipyridine with potassium dichromate in sulfuric acid is reported.
Induction of mesomorphism through supramolecular association in coordination Pd (II) compounds of dialkyl 2,2′-bipyridine-4,4′-dicarboxylates
Pucci, Daniela,Barberio, Giovanna,Crispini, Alessandra,Ghedini, Mauro,Francescangeli, Oriano
, p. [325]/155-[335]/165 (2003)
A scries of three 4,4′-disubstituted-2,2′-bipyridines and the corresponding mononuclear cis-dichloro palladium(II) complexes have been synthesized None of the ligands show mesomorphisrn. Upon their complexation to Pd(II) the peculiar structural arrangement characterized by intermolecular associations of the new derivatives induces mesogenic properties, confirming the new and exciting role of the coordination chemistry in metal-mediated formation of liquid crystals.
Synthesis of a Water-Soluble, Soft N-Donor BTzBP Ligand Containing only CHON
Albright, Savannah G.,Ali, Bakr,Chapman, Hayley A.,Cheng, Yijie,Cusic, Rachel M.,Friese, Seth J.,Hartlove, Nathan B.,Labb, Samantha A.,Marr, Alissa N.,Masteran, Conner J.,Timmons, Miranda
supporting information, p. 1384 - 1388 (2020/08/03)
A hydrophilic ligand that contains only C, H, O, and N substituents and uses a 6,6′-bis(1 H -1,2,3-triazol-4-yl)-2,2′-bipyridine (BTzBP) structural core has been synthesized. The effect of adding water-soluble groups onto extractant ligands has been extensively studied to facilitate the efficient partitioning of 4f and transuranic 5f elements for the treatment of spent nuclear fuel. Soft, N-donor ligands exhibit greater binding affinities for the trivalent actinides over the trivalent lanthanides, making BTzBP ligands an ideal candidate in the search for extractants to be used on an industrial scale. To date, hydrophobic BTzBPs have been shown to exhibit physical and chemical properties that might be conducive to nuclear waste processing conditions. However, hydrophilic BTzBPs have yet to be reported. Herein, we show the synthesis of a hydrophilic BTzBP ligand featuring cationic water solubilizing groups attached to the bipyridal rings.
Chromium(VI) oxide-mediated oxidation of polyalkyl-polypyridines to polypyridine-polycarboxylic acids with periodic acid
Yamazaki, Shigekazu
supporting information, p. 2210 - 2218 (2019/06/25)
4,4′-Dicarboxy-2,2′-bipyridine was synthesized quantitatively by chromium(VI) oxide-mediated oxidation of 4,4′-dimethyl-2,2′-bipyridine or 4,4′-diethyl-2,2′-bipyridine with periodic acid as the terminal oxidant in sulfuric acid. 5,5′-Dicarboxy-2,2′-bipyridine and 6,6’-dicarboxy-2,2′-bipyridine were also synthesized by the method from the corresponding dimethyl bipyridines in excellent yields. 4,4′,4″-Tricarboxy-2,2′:6′,2″-terpyridine was obtained in 80% yield from 4,4′,4″-triethyl-2,2′:6′,2″-terpyridine, and 4,4′,4″,4′″-tetracarboxy-2,2′:6′,2″:6″,2′″-quaterpyridine was obtained in 72% yield from 4,4′,4″,4′″-tetraethyl-2,2′:6′,2″:6″,2′″-quaterpyridine by the same procedure.
Rational Design of Phosphorescent Iridium(III) Complexes for Selective Glutathione Sensing and Amplified Photodynamic Therapy
Huang, Tianci,Yu, Qi,Liu, Shujuan,Zhang, Kenneth Yin,Huang, Wei,Zhao, Qiang
, p. 576 - 586 (2018/11/23)
It is a huge challenge to avoid irreversible damage to normal tissues during irradiation in photodynamic therapy (PDT) for cancer. An effective strategy is to develop smart photosensitizers, which exhibit amplified generation of reactive oxygen species (ROS) through triggering specific reaction in the tumor microenvironment. In this work, we designed a class of glutathione (GSH)-activatable photosensitizers (Ir1 and Ir4) based on an effective strategy of GSH-induced nucleophilic substitution reaction. The addition of GSH, induced changes in both phosphorescence intensity and lifetime of photosensitizers with high sensitivity. Importantly, the amount of singlet oxygen generated was increased significantly by GSH-induced activation reaction. Hence, the photosensitizers can selectively distinguish cancer cells from normal cells through luminescence and lifetime imaging, and can amplify PDT effects in cancer cells, owing to the evidently higher level of GSH compared to normal cells. This work presents a novel paradigm for GSH-amplified PDT against cancer cells and provides a new avenue for smart-responsive theranostic systems that can avoid nonspecific damage to normal cells.
