102437-81-0Relevant articles and documents
Antimicrobial Properties of Mono-and Di-fac-rhenium Tricarbonyl 2-Pyridyl-1,2,3-triazole Complexes
Kumar, Sreedhar V.,Lo, Warrick K. C.,Brooks, Heather J. L.,Hanton, Lyall R.,Crowley, James D.
, p. 489 - 498 (2016)
A family of mono-and di-fac-rhenium tricarbonyl 2-pyridyl-1,2,3-triazole complexes with different aliphatic and aromatic substituents was synthesized in good-to-excellent yields (46-99%). The complexes were characterized by 1H and 13
Dumbbells, trikes and quads: Organic-inorganic HYBRID NANOARCHITECTURES BASED on "cLICKED" GOLD NANOPARTICLES
Sander, Fabian,Fluch, Ulrike,Hermes, Jens Peter,Mayor, Marcel
, p. 349 - 359 (2014)
The controlled assembly of gold nanoparticles in terms of the spatial arrangement and number of particles is essential for many future applications like electronic devices, sensors and labeling. Here an approach is presented to build up oligomers of mono functionalized gold nanoparticles by the use of 1,3-bipolar azide alkyne cycloaddition click chemistry. The gold nanoparticles of 1.3 nm diameter are stabilized by one dendritic thioether ligand comprising an alkyne function. Together with di-, tri- and tetra-azide linker molecules the gold nanoparticle can be covalently coupled by a wet chemical protocol. The reaction is tracked with IR and UV-vis spectroscopy and the yielded organic-inorganic hybrid structures are analyzed by transmission electron microscopy. To evaluate the success of this click chemistry reaction statistical analysis of the formed oligomers is performed. The geometric and spatial arrangements of the found oligomers match perfectly the calculated values for the used linker molecules. Dimers, trimers and tetramers could be identified after the reaction with the corresponding linker molecule. The results of this model reaction suggest that the used click chemistry protocol is working well with mono functionalized gold nanoparticles. Functionalized gold nanoparticles are interlinked by a click chemistry protocol into defined oligomers. The spatial and geometric arrangement is directed by the size and numbers of functional moieties of the linker molecule. Electron transmission microscopy reveal the formation of dimers, trimers and tetramers.
Ionic liquid brush as a highly efficient and reusable catalyst for on-water nucleophilic substitutions
Li, Jing,Cao, Jing-Jing,Wei, Jun-Fa,Shi, Xian-Ying,Zhang, Li-Hui,Feng, Jin-Juan,Chen, Zhan-Guo
, p. 229 - 233 (2011)
A very efficient and reusable catalyst has been developed for the on-water nucleophilic substitution of alkyl halides and tosylates with azide or thiocyanate in excellent to quantitative yields. The reaction proceeds smoothly and cleanly without any organic cosolvent or other adductive, and the brush can be reused at least 10 times without noticeable loss of the catalytic activity. The high efficiency, simplicity of product and catalyst isolation, outstanding recyclability, and organic-solvent-free conditions show promise for the use of this catalyst in the laboratory and in industry. A highly efficient and reusable ionic liquid brush catalyst has been developed for the on-water nucleophilic substitution of alkyl halides and tosylates with azide or thiocyanate in excellent to quantitative yields without any organic cosolvent or other adductive. The catalyst can be reused at least 10 times without noticeable loss of the catalytic activity. Copyright
Catalysis of C-C cross-coupling reactions in aqueous solvent by bis- and tris(ferrocenyltriazolylmethyl)arene-β-cyclodextrin-stabilized Pd 0 nanoparticles
Liang, Liyuan,Diallo, Abdou K.,Salmon, Lionel,Ruiz, Jaime,Astruc, Didier
, p. 2950 - 2958 (2012)
Mono-, bis-, and tris(4-ferrocenyl-1,2,3-triazolylmethyl)arene-β- cyclodextrin adducts have been used to prepare new Pd0 nanoparticle (PdNP) catalysts for C-C cross-coupling reactions in EtOH/H2O. The results show that these catalysts work well in Miyaura-Suzuki and Heck reactions with iodoarenes at 25 and 80 °C, respectively, with turnover numbers (TONs) of up to 31000 for standard Miyaura-Suzuki reactions of PhI when 10 ppm of the Pd catalyst (5 nm PdNPs) were used. The results show the benefit for PdNP catalysis of encapsulating hydrophobic catalytic systems between peripheral water-solubilizing cyclodextrins as bolamphiphile-like materials because the open monoferrocenyltriazolylmethylbenzene system shows a considerably reduced catalytic efficiency compared with bis- and tris(4-ferrocenyl-1,2,3- triazolylmethyl)arene-β-cyclodextrin adducts. Copyright
Bis-triazolium containing macrocycles, pseudorotaxanes and interlocked structures for anion recognition
White, Nicholas G.,Lovett, Henry G.,Beer, Paul D.
, p. 12133 - 12147 (2014)
Two bis-triazole macrocycles were prepared by the copper(i)-catalysed azide alkyne cycloaddition of a bis-azide and 1,6-heptadiyne or 1,3-diethynylbenzene. Upon alkylation of one of these to give the dicationic bis-triazolium cycle, a potent receptor was generated which was demonstrated to be selective for sulfate. Two acyclic bis-triazolium receptors were also synthesized and the halide anion recognition properties of these systems investigated, as well as their ability to form anion templated pseudorotaxanes with an isophthalamide macrocycle. Interestingly, the propyl-linked bis-triazolium host displayed stronger anion binding affinities than the analogous 1,3-phenyl-linked system, although the phenyl-linked receptor formed a more stable halide anion templated pseudorotaxane. An acyclic bis-triazolium threading component produced a stable sulfate anion templated pseudorotaxane with a bis-triazolium macrocycle, which was used to synthesise a tetra-triazolium catenane. An anion templated stoppering strategy was used to prepare a bis-triazolium rotaxane host system which binds halide anions selectively over dihydrogenphosphate in competitive 1:1 CDCl3:CD3OD solvent media.
[3 + 3] Cycloaddition of azides with in situ formed azaoxyallyl cations to synthesize 1,2,3,4-Tetrazines
Xu, Xiaoying,Zhang, Kaifan,Li, Panpan,Yao, Hequan,Lin, Aijun
, p. 1781 - 1784 (2018)
A formal [3 + 3] cycloaddition reaction between azides and in situ formed azaoxyallyl cations has been realized. This reaction provided an efficient and practical pathway to synthesize 1,2,3,4-tetrazines in good yields under mild conditions. Biologically active molecules could also be well compatible, highlighting the potential value of this reaction.
Greatly enhanced thermo-oxidative stability of polybenzoxazine thermoset by incorporation of m-carborane
Huang, Xin,Zhang, Qiuhong,Meng, Zheng,Gu, Jiangjiang,Jia, Xudong,Xi, Kai
, p. 973 - 980 (2015)
Novel polybenzoxazine precursor containing m-carborane unit in the main-chain has been firstly synthesized through click reaction of diazidomethyl m-carborane (DAMC) and diacetylene bisbenzoxazine (DABB). Meanwhlie, the traditional polybenzoxazine precursor was also prepared through click reaction of diazidomethyl p-benzene (DAPB) and DABB as a control. 1H NMR was used to confirm the structures of the monomers and the resulting polymers. FT-IR and differential scanning calorimetry (DSC) were used to study the curing behavior of carborane-containing benzoxazine polymer (CCBP). Dynamic mechanical analysis (DMA) study demonstrated that the cured CCBP had high storage moduli and high Tg. Thermogravimetric analysis (TGA) and ablation test showed that the cured CCBP had outstanding thermo-oxidative stability. During thermal ablation of cured CCBP, organic material was degraded, and a passivation layer with oxidized m-carboranes was formed, which prevented the underlying polymer from further degradation.
Hyper-reticulated calixarene polymers: A new example of entirely synthetic nanosponge materials
Spinella, Alberto,Russo, Marco,Di Vincenzo, Antonella,Martino, Delia Chillura,Lo Meo, Paolo
, p. 1498 - 1507 (2018)
New calixarene-based nanosponges (CaNSs), i.e., hyper-reticulated polymers constituted by calixarene monomer units joined by means of bis(1, 2, 3-trialzolyl)alkyl linkers, were synthesized, characterized and subjected to preliminary tests to assess their supramolecular absorption abilities towards a set of suitable organic guests, selected as pollutant models. The synthesis was accomplished by means of a CuAAC reaction between a tetrakis(propargyloxy)calix[4]arene and an alkyl diazide. The formation of the polymeric network was assessed by means of FTIR and 13C{1H} CP-MAS solid-state NMR techniques, whereas morphological characterization was provided by SEM microghaphy. The materials were proved to possess pH-dependent sequestration abilities, due to the presence of the weakly basic triazole linkers. Sequestration efficiency indeed depends on the effective occurrence of both electrostatic and hydrophobic interactions between the guest and the polymer lattice. Thus, our CaNS nanosponges can be considered as a new class of purely synthetic smart absorbent materials.
An Autonomous Chemical Robot Discovers the Rules of Inorganic Coordination Chemistry without Prior Knowledge
Bell, Nicola L.,Cronin, Leroy,Henson, Alon,Kowalski, Daniel J.,Long, De-Liang,Porwol, Luzian
, p. 11256 - 11261 (2020)
We present a chemical discovery robot for the efficient and reliable discovery of supramolecular architectures through the exploration of a huge reaction space exceeding ten billion combinations. The system was designed to search for areas of reactivity f
Syntheses and biological activity of bisdaunorubicins
Zhang, Guisheng,Fang, Lanyan,Zhu, Lizhi,Sun, Duxin,Wang, Peng George
, p. 426 - 434 (2006)
To study the length and flexibility of the linkers between two monomers of bisdaunorubicins for their activity against cancer cells, seven bisdaunorubicins were rationally designed and synthesized through click chemistry. Their cytotoxicity was tested in
