117585-58-7Relevant articles and documents
A three-photon probe with dual emission colors for imaging of Zn(ii) ions in living cells
Mandal, Amal Kumar,He, Tingchao,Maji, Swarup Kumar,Sun, Handong,Zhao, Yanli
, p. 14378 - 14381 (2014)
A novel three-photon probe for the imaging of exogenous Zn(ii) ions in live cells with varying emission colors under three-photon excitation is developed. The tuning of the charge transfer state and the emission color of the probe was also demonstrated in the presence of acid.
Functionalized gold nanoparticles as phosphorescent nanomaterials and sensors
Ipe, Binil Itty,Yoosaf, Karuvath,Thomas, Kakkudiyil George
, p. 1907 - 1913 (2006)
Ligand-capped gold nanoparticles were synthesized by capping monothiol derivatives of 2,2′-dipyridyl onto the surface of Au nanoparticles (Au-BT). The average size of the metal core is around 4 nm, with a shell of ～340 bipyridine ligands around the Au nanoparticle. The high local concentration of the chelating ligands (～5 M) around the Au nanoparticle makes these particles excellent ion sponges, and their complexation with Eu III/TbIII ions yields phosphorescent nanomaterials. Absorption spectral studies confirm a 1:3 complexation between Eu III/TbIII ions and bipyridines, functionalized on the surface of Au nanoparticles. The red-emitting Au-BT:EuIII complex exhibits a long lifetime of 0.36 ms with six line-like emission peaks, whereas the green-emitting Au-BT:TbIII complex exhibits a lifetime of 0.7 ms with four line-like emission peaks. These phosphorescent nanomaterials, designed by linking BT:EuIII complexes to Au nanoparticles, were further utilized as sensors for metal cations. A dramatic decrease in the luminescence was observed upon addition of alkaline earth metal ions (Ca2+, Mg2+) and transition metal ions (Cu2+, Zn2+, Ni2+), resulting from an isomorphous substitution of EuIII ions, whereas the luminescence intensity was not influenced by the addition of Na+ and K+ ions. Direct interaction of bipyridine-capped Au nanoparticles with Cu2+ ions brings the nanohybrid systems closer, leading to the formation of three-dimensional superstructures. Strong interparticle plasmon interactions were observed in these closely spaced Au nanoparticles.
New scaffolds for supramolecular chemistry: Upper-rim fully tethered 5-methyleneureido-5′-methyl-2,2′-bipyridyl cyclodextrins
Heck, Romain,Dumarcay, Florence,Marsura, Alain
, p. 2438 - 2445 (2002)
Seven upper-rim fully tethered cyclodextrins (URFT-CDs) have been synthesised in a good average coupling yield using the one-step "phosphine imide" approach and their metal complexation behaviour with lanthanides and transition metals was explored. We observed that the A-TE-E light conversion process (antennae effect) occurs in the URFT-CD lanthanide complexes. A molecular redox switch based on the corresponding iron complexes is also reported. A reversible intramolecular translocation of the FeII and FeIII ions, between two distinct binding cavities has been monitored spectroscopically and achieved by chemical triggering. Finally, a negative allosteric control of ion recognition through the formation of a CD pseudocryptand is discussed.
Construction and structure studies of DNA-bipyridine complexes as versatile scaffolds for site-specific incorporation of metal ions into DNA
Wang, Rui,Ranganathan, Srivathsan V.,Haruehanroengra, Phensinee,Mao, Song,Scalabrin, Matteo,Fabris, Daniele,Chen, Alan,Liu, Hehua,Hassan, Abdalla E.A.,Gan, Jianhua,Sheng, Jia
, p. 1 - 11 (2018)
The facile construction of metal–DNA complexes using ‘Click’ reactions is reported here. A series of 2′-propargyl-modified DNA oligonucleotides were initially synthesized as structure scaffolds and were then modified through ‘Click’ reaction to incorporate a bipyridine ligand equipped with an azido group. These metal chelating ligands can be placed in the DNA context in site-specific fashion to provide versatile templates for binding various metal ions, which are exchangeable using a simple EDTA washing-and-filtration step. The constructed metal–DNA complexes were found to be thermally stable. Their structures were explored by solving a crystal structure of a propargyl-modified DNA duplex and installing the bipyridine ligands by molecular modeling and simulation. These metal–DNA complexes could have wide applications as novel organometallic catalysts, artificial ribonucleases, and potential metal delivery systems.
Synthesis of polydendate acyclic and macrocyclic polyamine ligands bearing 2,2'-bipyridine or 2,2'-bipyridine N,N'-dioxide moieties
Ziessel, Raymond,Hissler, Muriel,Ulrich, Gilles
, p. 1339 - 1346 (1998)
The synthesis of various acyclic and macrocyclic complexing agents bearing bypyridine or bipyridine N,N'-dioxide substituents is reported. These ligands, which possess three, four, or six pendant units, have been prepared by a general synthetic protocol starling from the mono(bromomethyl)-2,2'-bipyridine or mono(bromomethyl)-2,2'-bipyridine N,N'-dioxide derivatives and the corresponding amine in the presence of a mineral base. NMR and FAB-MS spectral data indicate that tripode 5 and hexapode 9, respectively form stable, highly colored and redox-active mono-and diiron(II) complexes.
Synthesis, structure and inclusion properties of cone-tris{[(5′- methyl-2,2′-bipyridyl)-5-yl]oxycarbonylmethoxy}hexahomotrioxacalix[3]arene
Ni, Xin-Long,Takimoto, Masashi,Xi, Zeng,Yamato, Takehiko
, p. 231 - 237 (2011)
Hexahomotrioxacalix[3]arene having [(5′-methyl-2,2′-bipyridyl)- 5-yl]oxycarbonylmethoxy group with cone conformation was prepared, which shows strong Ag+ affinity and acts as a ditopic receptor for Ag+ and nBuNH3 +/s
Bifunctional DNA architectonics: Three-way junctions with sticky perylene bisimide caps and a central metal lock
Stubinitzky, Claudia,Bijeljanin, Andrea,Antusch, Linda,Ebeling, Daniel,H?lscher, Hendrik,Wagenknecht, Hans-Achim
, p. 12009 - 12014 (2014)
A new type of a bifunctional DNA architecture based on a three way junction is developed that combines the structural motif of sticky perylene bisimide caps with a tris-bipyridyl metal ion lock in the center part. A clear stabilizing effect was observed in the presence of Fe3+, Ni2+ and Zn2+ by the formation of corresponding bipyridyl complexes in the branching part of the DNA three way junctions. The dimerization of the 5-terminally attached perylene diimides (PDI) chromophores by hydrophobic interactions can be followed by significant changes in the UV/Vis absorption and steady-state fluorescence. The PDI-mediated DNA assembly occurs at temperatures below the melting temperature and is not influenced by the metal-ion bipyridyl locks in the central part. The corresponding AFM images revealed the formation of higher-ordered structures as the result of DNA assemblies mediated by the PDI interactions.
Directed synthesis of monofunctionalized 5,5'-disubstituted 2,2'- bipyridines and their first application as metallo-supramolecular initiators
Schubert, Ulrich S.,Eschbaumer, Christian,Hochwimmer, Georg
, p. 8643 - 8644 (1998)
Monofunctionalized 5,5'-disubstituted 2,2'-bipyridines were synthesized in very high yields and used in a first application for the construction of a metal centered star-like AB block copolymer.
Evaluation of multisite polypyridyl ligands as platforms for the synthesis of Rh/Zn, Rh/Pd, and Rh/Pt heterometallic complexes
Goforth, Sarah K.,Walroth, Richard C.,McElwee-White, Lisa
, p. 5692 - 5701 (2013)
Ligands containing linked dipicolylamine (dpa) and bipyridine (bpy) sites have been utilized in the synthesis of monometallic and heterometallic complexes. The two sites have different selectivities for metal binding, which allows preferential formation of singly metalated complexes. The dpa site of the ligands has been observed to bind selectively to Zn2+, Pd 2+, and Pt2+, while the bpy site binds selectively to Rh+. Addition of a second metal then results in the formation of heterometallic products. In the presence of CD3OD, the heterometallic Rh/Pt and Rh/Pd complexes undergo rapid selective H/D exchange of one of the diastereotopic protons of the dpa methylene group.
Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A Meta-Selective C-H Borylation of Aromatic Quaternary Ammonium Salts
Davis, Holly J.,Mihai, Madalina T.,Phipps, Robert J.
supporting information, p. 12759 - 12762 (2016/10/13)
The use of noncovalent interactions to direct transition-metal catalysis is a potentially powerful yet relatively underexplored strategy, with most investigations thus far focusing on using hydrogen bonds as the controlling element. We have developed an ion pair-directed approach to controlling regioselectivity in the iridium-catalyzed borylation of two classes of aromatic quaternary ammonium salts, leading to versatile meta-borylated products. By examining a range of substituted substrates, this provides complex, functionalized aromatic scaffolds amenable to rapid diversification and more broadly demonstrates the viability of ion-pairing for control of regiochemistry in transition-metal catalysis.
