113682-56-7Relevant articles and documents
Enantioselective adsorption in homochiral metal-organic frameworks: The pore size influence
Gu, Zhi-Gang,Grosjean, Sylvain,Br?se, Stefan,W?ll, Christof,Heinke, Lars
, p. 8998 - 9001 (2015)
Uptake experiments in thin films of isoreticular chiral MOFs of type Cu2(Dcam)2(L) with identical stereogenic centers but different pore dimensions show that the enantioselectivity is significantly influenced by the pore size. The hi
One-Pot Synthesis and Redox Properties of Conjugation-Extended 4,4'-Bipyridines and Related Compounds. New Ligands Consisting of a Heterocyclic Three-Ring Assembly
Takahashi, Kazuko,Nihira, Takayasu
, p. 1855 - 1859 (1992)
Dipyridyl-substituted heterocycles such as 2,5-di(4-pyridyl)thiophene 3, 2,5-di(4-pyridyl)furan 4, 2,5-di(4-pyridyl)thienothiophene 7, 1,4-di(4-pyridyl)benzene 6, 2,5-di(2-pyridyl)thiophene 8, and 2,5-di(3-pyridyl)thiophene 9 have been efficiently
Achieving a rare breathing behavior in a polycatenated 2 D to 3 D net through a pillar-ligand extension strategy
Zhao, Xiaoliang,Liu, Fuling,Zhang, Liangliang,Sun, Di,Wang, Rongming,Ju, Zhangfeng,Yuan, Daqiang,Sun, Daofeng
, p. 649 - 652 (2014)
Through a pillar-ligand extension strategy, a rare breathing behavior in polycatenated 2D→3D nets has been achieved. Three variants exhibit interesting sorption properties that range from non-breathing to breathing behaviors, which is influenced by the angles between the pillars and the single honeycomb layers. The increase in pillar length does not lead to an increase in polycatenation multiplicity, which is controlled by the length of intralayer tripodal carboxylate. It also does not induce obviously expanded interlayer separations but occupies much more the free voids, and as a consequence, a smaller pore volume is obtained. This suggests that in 2D→3D polycatenated bilayer metal-organic frameworks, the porosity is not always enhanced by increasing the length of the interlayer pillars with the intralayer linker remaining unchanged. Copyright
Viologen Derivatives Extended with Aromatic Rings Acting as Negative Electrode Materials for Use in Rechargeable Molecular Ion Batteries
Kato, Minami,Sano, Hikaru,Kiyobayashi, Tetsu,Yao, Masaru
, p. 2379 - 2385 (2020)
Many types of batteries have been proposed as next-generation energy-storage systems. One candidate is a rocking-chair-type “molecular ion battery” in which a molecular ion, instead of Li+, works as a charge carrier. Previously, we reported a viologen-type derivative as a negative electrode material that releases and receives PF6? anions during the charge–discharge process; however, its redox potential was not satisfactorily low. Further, the two potential plateaus of this material (difference=0.5 V) should be reduced. In this study, PF6? salts of viologen (bipyridinium) derivatives extended by aromatic rings were synthesized to obtain a negative electrode material with a lower redox potential and small potential change during the charge and discharge processes. Some of the synthesized viologen derivatives were fluorescent even in solid-state electrodes. In the half-cell configuration, the prepared negative electrode materials showed average voltages of approximately 2 V (vs. Li+/Li), which is lower than that of conventional viologen derivatives.
Chemical control of spin propagation between heterometallic rings
Faust, Thomas B.,Bellini, Valerio,Candini, Andrea,Carretta, Stefano,Lorusso, Giulia,Allan, David R.,Carthy, Laura,Collison, David,Docherty, Rebecca J.,Kenyon, Jasbinder,MacHin, John,McInnes, Eric J. L.,Muryn, Christopher A.,Nowell, Harriott,Pritchard, Robin G.,Teat, Simon J.,Timco, Grigore A.,Tuna, Floriana,Whitehead, George F. S.,Wernsdorfer, Wolfgang,Affronte, Marco,Winpenny, Richard E. P.
, p. 14020 - 14030 (2011)
We present a synthetic, structural, theoretical, and spectroscopic study of a family of heterometallic ring dimers which have the formula [{Cr 7NiF3(Etglu)(O2CtBu)15} 2(NLN)], in which Etglu is the pentadeprotonated form of the sugar N-ethyl-D-glucamine, and NLN is an aromatic bridging diimine ligand. By varying NLN we are able to adjust the strength of the interaction between rings with the aim of understanding how to tune our system to achieve weak magnetic communication between the spins, a prerequisite for quantum entanglement. Micro-SQUID and EPR data reveal that the magnetic coupling between rings is partly related to the through-bond distance between the spin centers, but also depends on spin-polarization mechanisms and torsion angles between aromatic rings. Density functional theory (DFT) calculations allow us to make predictions of how such chemically variable parameters could be used to tune very precisely the interaction in such systems. For possible applications in quantum information processing and molecular spintronics, such precise control is essential.
Eliminating the need for independent counterions in the construction of metal-organic rotaxane frameworks (MORFs)
Knight, Lisa K.,Vukotic, V. Nicholas,Viljoen, Elizabeth,Caputo, Christopher B.,Loeb, Stephen J.
, p. 5585 - 5587 (2009)
The combination of a disulfonated-dibenzo-24crown-8 ether wheel and a dicationic 1,2-bis(pyridinium)ethane axle yields a neutral [2]pseudorotaxane which in combination with neutral metallic units such as a Cu(ii)benzoate paddlewheel or Cu(i)Br unit yields
Palladium(O)/LiCl Promoted Cross-Coupling Reaction of (4-Pyridyl)stannanes and Aromatic Bromides: Easy Access to Poly(4-pyridyl)-Substituted Aromatics
Fujita, Makoto,Oka, Hiroko,Ogura, Katsuyuki
, p. 5247 - 5250 (1995)
A PdCl2(PPh3)2/LiCl catalyst effectively promoted the cross-coupling reaction of trimethyl(4-pyridyl)stannane and aromatic polybromides to offer easy access to poly(4-pyridyl)-substituted aromatic compounds.
ExBox: A polycyclic aromatic hydrocarbon scavenger
Barnes, Jonathan C.,Jurí?ek, Michal,Strutt, Nathan L.,Frasconi, Marco,Sampath, Srinivasan,Giesener, Marc A.,McGrier, Psaras L.,Bruns, Carson J.,Stern, Charlotte L.,Sarjeant, Amy A.,Stoddart, J. Fraser
, p. 183 - 192 (2013)
A template-directed protocol, which capitalizes on donor-acceptor interactions, is employed to synthesize a semi-rigid cyclophane (ExBox 4+) that adopts a box-like geometry and is comprised of π-electron-poor 1,4-phenylene-bridged ("extended") bipyridinium units (ExBIPY2+). ExBox4+ functions as a high-affinity scavenger of an array of different polycyclic aromatic hydrocarbons (PAHs), ranging from two to seven fused rings, as a result of its large, accommodating cavity (approximately 3.5 A? in width and 11.2 A? in length when considering the van der Waals radii) and its ability to form strong non-covalent bonding interactions with π-electron-rich PAHs in either organic or aqueous media. In all, 11 PAH guests were observed to form inclusion complexes with ExBox4+, with coronene being the largest included guest. Single-crystal X-ray diffraction data for the 11 inclusion complexes ExBox 4+?PAH as well as UV/vis spectroscopic data for 10 of the complexes provide evidence of the promiscuity of ExBox4+ for the various PAHs. Nuclear magnetic resonance spectroscopy and isothermal titration calorimetric analyses of 10 of the inclusion complexes are employed to further characterize the host-guest interactions in solution and determine the degree with which ExBox4+ binds each PAH compound. As a proof-of-concept, a batch of crude oil from Saudi Arabia was subjected to extraction with the water-soluble form of the PAH receptor, ExBox·4Cl, resulting in the isolation of different aromatic compounds after ExBox·4Cl was regenerated.
ExTzBox: A Glowing Cyclophane for Live-Cell Imaging
Roy, Indranil,Bobbala, Sharan,Zhou, Jiawang,Nguyen, Minh T.,Nalluri, Siva Krishna Mohan,Wu, Yilei,Ferris, Daniel P.,Scott, Evan Alexander,Wasielewski, Michael R.,Stoddart, J. Fraser
, p. 7206 - 7212 (2018)
The ideal fluorescent probe for live-cell imaging is bright and non-cytotoxic and can be delivered easily into the living cells in an efficient manner. The design of synthetic fluorophores having all three of these properties, however, has proved to be challenging. Here, we introduce a simple, yet effective, strategy based on well-established chemistry for designing a new class of fluorescent probes for live-cell imaging. A box-like hybrid cyclophane, namely ExTzBox·4X (6·4X, X = PF6-, Cl-), has been synthesized by connecting an extended viologen (ExBIPY) and a dipyridyl thiazolothiazole (TzBIPY) unit in an end-to-end fashion with two p-xylylene linkers. Photophysical studies show that 6·4Cl has a quantum yield φF = 1.00. Furthermore, unlike its ExBIPY2+ and TzBIPY2+ building units, 6·4Cl is non-cytotoxic to RAW 264.7 macrophages, even with a loading concentration as high as 100 μM, presumably on account of its rigid box-like structure which prevents its intercalation into DNA and may inhibit other interactions with it. After gaining an understanding of the toxicity profile of 6·4Cl, we employed it in live-cell imaging. Confocal microscopy has demonstrated that 64+ is taken up by the RAW 264.7 macrophages, allowing the cells to glow brightly with blue laser excitation, without any hint of photobleaching or disruption of normal cell behavior under the imaging conditions. By contrast, the acyclic reference compound Me2TzBIPY·2Cl (4·2Cl) shows very little fluorescence inside the cells, which is quenched completely under the same imaging conditions. In vitro cell investigations underscore the significance of using highly fluorescent box-like rigid cyclophanes for live-cell imaging.
{[Ru(bda)]:XLy}n cross-linked coordination polymers: Toward efficient heterogeneous catalysis for water oxidation in an organic solvent-free system
Zheng, Tao,Li, Lianwei
, p. 2526 - 2536 (2018)
Recently, the development of polymeric catalysts for water splitting has received an increasing amount of attention. In this study, we successfully developed a few novel cross-linked coordination polymers (CCPs) with the formula {[Ru(bda)]xLy}n as efficient heterogeneous catalysts for water oxidation in an organic solvent-free system, where Ru(bda) represents the catalytic center. Detailed water oxidation catalytic kinetics studies suggested that single-site water nucleophilic attack (WNA) is the general mechanism applied to these polymeric catalysts, which is different to the small-molecular reference, [Ru(bda)(pic)2] (pic = 4-picoline). The experimental evidence also indicated the importance of interfacial wettability and the existence of the Ru(bda)-macrocyclic fragments in the polymer network in determining the overall catalytic activity. More interestingly, end-capping modification via the pyridine/DMSO exchange reaction further removed the residual Ru(DMSO)x moieties on the surfaces of the polymer network, which leads to the improved performance with an impressive TOF of ～4.6 s-1 and TON of ～750 in an organic solvent-free system, which are superior to [Ru(bda)(pic)2]. The rate of catalysis is among the highest for a heterogeneous system reported to date. An electrochemical study showed the polymeric catalysts were also promising electrode materials for electrocatalytic water oxidation and an electrode based on CCP/Nafion/ITO maintained ～73% of its initial activity after 27 cycles under the optimal conditions.
