67227-90-1Relevant academic research and scientific papers
Evidence for halogen bond covalency in acyclic and interlocked halogen-bonding receptor anion recognition
Robinson, Sean W.,Mustoe, Chantal L.,White, Nicholas G.,Brown, Asha,Thompson, Amber L.,Kennepohl, Pierre,Beer, Paul D.
, p. 499 - 507 (2015)
The synthesis and anion binding properties of novel halogen-bonding (XB) bis-iodotriazole-pyridinium-containing acyclic and [2]catenane anion host systems are described. The XB acyclic receptor displays selectivity for acetate over halides with enhanced anion recognition properties compared to the analogous hydrogen-bonding (HB) acyclic receptor. A reversal in halide selectivity is observed in the XB [2]catenane, in comparison to the acyclic XB receptor, due to the interlocked hosts unique three-dimensional binding cavity, and no binding is observed for oxoanions. Notable halide anion association constant values determined for the [2]catenane in competitive organic-aqueous solvent mixtures demonstrate considerable enhancement of anion recognition as compared to the HB catenane analogue. X-ray crystallographic analysis of a series of halide catenane complexes reveal strong XB interactions in the solid state. These interactions were studied using Cl and Br K-edge X-ray Absorption Spectroscopy (XAS) indicating intense pre-edge features characteristic of charge transfer from the halide to its bonding partner (σAX←X- ← X1s), and providing a direct measure of the degree of covalency in the halogen bond(s). The data reveal that the degree of covalency is similar to that which is observed in transition metal coordinate covalent bonds. These results are supported by DFT results, which correlate well with the experimental data.
The exploration of hydrogen bonding properties of 2,6- and 3,5-diethynylpyridine by IR spectroscopy
Vojta, Danijela,Kova?evi?, Goran,Vazdar, Mario
, p. 1912 - 1923 (2015)
Hydrogen bonding properties of 2,6- and 3,5-diethynylpyridine were analyzed by exploring of their interactions with trimethylphosphate, as hydrogen bond acceptor, or phenol, as hydrogen bond donor, in tetrachloroethene C2Cl4. The employment of IR spectroscopy enabled unravelling of their interaction pattern as well as the determination of their association constants (Kc) and standard reaction enthalpies (ΔrHθ). The association of diethynylpyridines with trimethylphosphate in stoichiometry 1:1 is established through CH?O hydrogen bond, accompanied by the secondary interaction between CC moiety and CH3 group of trimethylphosphate. In the complexes with phenol, along with the expected OH?N interaction, CC?HO interaction is revealed. In contrast to 2,6-diethynylpyridine where the spatial arrangement of hydrogen bond accepting groups enables the simultaneous involvement of phenol OH group in both OH?N and OH?CC hydrogen bond, in the complex between phenol and 3,5-diethynylpyridine this is not possible. It is postulated that cooperativity effects, arisen from the certain type of resonance-assisted hydrogen bonds, contribute the stability gain of the latter. Associations of diethynylpyridines with trimethylphosphate are characterized as weak (Kc ≈0.8-0.9 mol-1 dm3; -ΔrHθ ≈5-8 kJ mol-1), while their complexes with phenol as medium strong (Kc ≈5 mol-1 dm3; -ΔrHθ ≈15-35 kJ mol-1). Experimental findings on the studied complexes are supported with the calculations conducted at B3LYP/6-311++G(d,p) level of theory in the gas phase. Two conformers of diethynylpyridine?trimethylphosphate dimers are formed via CH?O interaction, whereas dimers between phenol and diethynylpyridines are established through OH?N interaction.
A Triazole Functionalized txt-Type Metal-Organic Framework with High Performance for CH4Uptake and Selective CO2Adsorption
Cui, Huihui,Jiang, Guomin,Qin, Guoping,Sun, Tongming,Tang, Yanfeng,Wang, Jin,Wang, Miao,Wang, Minmin,Wang, Su,Zhang, Lifang,Zhang, Mingxing,Zhang, Peipei
supporting information, p. 15646 - 15652 (2021/10/20)
The metal-organic framework (MOF) NTUniv-54 (NTUniv = Nantong University) was assembled via utilizing click chemistry with densely decorated trizole units and exposed metal sites, which exhibited the best methane working ability (197 cm3·cm-3 from 100 to 5 bar and 177 cm3·cm-3 from 65 to 5 bar at 298 K), and the lowest CO2 Qst of 22.8 kJ·mol-1 in all triazole-MOFs at room temperature.
Symmetric molecules with 1,4-triazole moieties as potent inhibitors of tumour-associated lactate dehydrogenase-A
Altamimi, Abdul-Malek S.,Abdel-Gawad, Sherif A.,Alafeefy, Ahmed M.,Balode, Agnese,Vozny, Igor,Pustenko, Aleksandrs,?alubovskis, Raivis,El Shikh, Mohey Eldin,Alasmary, Fatmah A. S.
, p. 147 - 150 (2018/01/02)
A series of symmetric molecules incorporating aryl or pyridyl moieties as central core and 1,4-substituted triazoles as a side bridge was synthesised. The new compounds were investigated as lactate dehydro-genase (LDH, EC 1.1.1.27) inhibitors. The cancer associated LDHA isoform was inhibited with IC50 = 117–174?μM. Seven compounds exhibited better LDHA inhibition (IC50 117–136?μM) compared to known LDH inhibitor–galloflavin (IC50 157?μM).
Functional organic click-materials: application in phosphorescent organic light emitting diodes
Kautny, Paul,Zhao, Chenyang,Kader, Thomas,St?ger, Berthold,Horkel, Ernst,Chen, Jiangshan,Ma, Dongge,Fr?hlich, Johannes,Lumpi, Daniel
, p. 12150 - 12160 (2017/03/08)
In the presented work click chemistry is utilized to introduce 1,2,3-triazoles as a functional linker in organic donor-acceptor materials. A systematic series of materials was prepared and characterized to investigate the effect of the linkage mode on the molecular properties. The 1,2,3-triazole linker allowed control of the degree of intramolecular charge transfer over a wide range depending on the substitution pattern of the triazole moiety. The prepared materials were successfully employed as host materials for green and red dopants in phosphorescent organic light emitting diodes. Thus, this work presents the first application of this novel linkage mode in the design and synthesis of functional π-conjugated organic donor-acceptor materials and their application in organic light emitting diodes.
The Utilization of Amide Groups to Expand and Functionalize Metal-Organic Frameworks Simultaneously
Lu, Zhiyong,Bai, Junfeng,Hang, Cheng,Meng, Fei,Liu, Wenlong,Pan, Yi,You, Xiaozeng
, p. 6277 - 6285 (2016/05/09)
A new stepwise ligand-elongation strategy by amide spacers is utilized to prepare isoreticularly high-porous metal-organic frameworks (MOFs), namely, quasi-mesoporous [Cu2(PDBAD)(H2O)]n (H4PDBAD=5,5′-((4,4′-((pyridine-3,5-dicarbonyl)bis(azanediyl))bis(benzoyl))bis(azanediyl))diisophthalic acid; NJU-Bai22: NJU-Bai for Nanjing University Bai's group), and mesoporous [Cu2(PABAD)(H2O)]n (H4PABAD=5,5′-((4,4′-((4,4′-((pyridine-3,5-dicarbonyl)bis(azanediyl))bis(benzoyl))bis (azanediyl))bis(benzoyl))bis(azanediyl))diisophthalic acid; NJU-Bai23). Compared with the prototypical MOF of [Cu2(PDAD)(H2O)]n (H4PDAD=5,5′-(pyridine-3,5-dicarbonyl)bis(azanediyl)diisophthalic acid; NJU-Bai21, also termed as PCN-124), both MOFs exhibit almost the same CO2 adsorption enthalpy and CO2 selectivity values, and better capacity for CO2 storage under high pressure; these results make them promising candidate materials for CO2 capture and sequestration. Interestingly, this new method, in comparison with traditional strategies of using phenyl or triple-bond spacers, is easier and cheaper, resulting in a better ability to retain high CO2 affinity and selectivity in MOFs with large pores and high CO2 storage capacity. Additionally, it may lead to the high thermal stability of the MOFs and also their tolerance to water, which is related to the balance between the density of functional groups and pore sizes. Therefore, this strategy could provide new opportunities to explore more functionalized mesoporous MOFs with high performance.
A catenane host system containing integrated triazole C-H hydrogen bond donors for anion recognition
White, Nicholas G.,Beer, Paul D.
supporting information; experimental part, p. 8499 - 8501 (2012/09/22)
A 3,5-bis(triazole)-pyridinium motif is integrated into a catenane structural framework via chloride anion templation. The catenane host system displays a high degree of selectivity for halide anions over dihydrogen phosphate.
Anion binding in aqueous media by a tetra-triazolium macrocycle
White, Nicholas G.,Beer, Paul D.,Carvalho, Silvia,Felix, Vitor
, p. 6951 - 6959,9 (2020/08/31)
Three tetra-triazole macrocycles were synthesized in good yields by the copper(i)-catalysed cycloaddition of bis-triazole azides and bis-alkynes. One of these was alkylated to give a cyclic tetra-triazolium receptor, which complexes anions strongly in competitive DMSO-water mixtures. In 1:1 DMSO-water, the tetracationic receptor exhibits a preference for the larger halides, bromide and iodide, with all halides associating more strongly than the oxoanion, acetate. The sulfate dianion is complexed far more strongly than any of the monobasic anions (Ka > 104 M-1). Quantum mechanics/molecular mechanics simulations corroborate the experimentally determined anion binding selectivity trends.
Efficient thermal conversion of poly(pyridinediylbutadiynylene)s to nitrogen-containing microporous carbon
Kijima, Masashi,Oda, Takayuki,Yamazaki, Takahisa,Tazaki, Yasunori,Nakamura, Junji
, p. 844 - 845 (2007/10/03)
Poly(pyridinediylbutadiynylene)s, a conjugated polymer alternatively consisted of the pyridine and butadiyne units, were synthesized by oxidative polycondensation of diethynylpyridine with the Hay catalyst. They converted to microporous carbons in high yi
Single-site modifications and their effect on the folding stability of m-phenylene ethynylene oligomers
Goto, Hirofumi,Heemstra, Jennifer M.,Hill, David J.,Moore, Jeffrey S.
, p. 889 - 892 (2007/10/03)
(Equation presented) The folded structure of a m-phenylene ethynylene oligomer is tolerant to single-site modifications to both the backbone sequence and end groups. The helical structure is reinforced by multiple noncovalent interactions, allowing the ol
