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Marie-Claire Giel Dr. Christopher J. Smedley Emily R. R. Mackie Taijie Guo Prof. Dr. Jiajia Dong Dr. Tatiana P. Soares da Costa Prof. Dr. John E. Moses 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(3):1197-1202
The boom in growth of 1,4-disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI-catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click-inspired protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1-substituted-1,2,3-triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts. 相似文献
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Marie‐Claire Giel Christopher J. Smedley Emily R. R. Mackie Taijie Guo Jiajia Dong Tatiana P. Soares da Costa John E. Moses 《Angewandte Chemie (International ed. in English)》2020,59(3):1181-1186
The boom in growth of 1,4‐disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI‐catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1‐substituted‐1,2,3‐triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click‐inspired protocol for the synthesis of 1‐substituted‐1,2,3‐triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal‐free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1‐substituted‐1,2,3‐triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1‐substituted triazolium sulfonyl fluoride salts. 相似文献
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Massoud Kaykhaii Greg W. Dicinoski Rebecca Smedley Janusz Pawliszyn Paul R. Haddad 《Journal of chromatography. A》2010,1217(20):3452-3456
The use of a functionalized latex nanoparticle coating as a new sorbent phase for solid-phase microextraction (SPME) was examined. By means of electrostatic absorption onto ionized silanol groups, a fused-silica rod was coated with polymeric nanoparticles functionalized with quaternary ammonium groups. Optimum conditions for the preparation of the coated fibre are presented. The fibre was used for the extraction of a mixture of seven anions from water samples which are analysed by coupling the SPME fibre to an ion chromatographic system via a special interface. The results obtained proved the suitability of this novel coating as a new SPME fibre. A linear calibration for the target analytes was achieved over the concentration range from 5 μg L−1 to 5 mg L−1 (r2 > 0.988), while limits of detection for these ions were all below 3.7 μg L−1 (S/N = 3). The reproducibility of a single fibre (n = 4) under similar conditions was between 7 and 12%, while the fibre to fibre reproducibility (n = 5) was between 8.9 and 14%. 相似文献
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Results of an experimental investigation into the thermal behavior and mechanical properties of a room-temperature-cured epoxy
adhesive (diglycidyl ether of bisphenol A, DGEBA) cross-linked with polyetheramines and filled with different fillers, namely
nanosilica, liquid rubber (CTBN), and clay, are reported. The nanosilica and liquid rubber increased the flexural strength
and elastic modulus of the adhesive systems; the addition of clay particles raised the elastic modulus significantly, but
embrittled the adhesive. Establishing a correct cure time is very important for bonded-in timber structures, as it will affect
the bond strength. A study on the effect of cure time on the flexural strength was carried out, from which it follows that
the adhesives should be cured for at least 20 days at room temperature. The damping characteristics and the glass-transition
temperature of the adhesives were determined by using a dynamic mechanical thermal analysis. The results showed that the filled
adhesives had a higher storage modulus, which was in agreement with the elastic moduli determined from static bending tests.
The introduction of the fillers increased its glass-transition temperature considerably.
Russian translation published in Mekhanika Kompozitnykh Materialov, Vol. 42, No. 5, pp. 599–614, September–October, 2006. 相似文献
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High‐quality single‐crystal and polycrystalline chemical‐vapor‐deposition diamond detectors with platinum contacts have been tested at the white‐beam X28C beamline at the National Synchrotron Light Source under high‐flux conditions. The voltage dependence of these devices has been measured under both DC and pulsed‐bias conditions, establishing the presence or absence of photoconductive gain in each device. Linear response consistent with the theoretically determined ionization energy has been achieved over eleven orders of magnitude when combined with previous low‐flux studies. Temporal measurements with single‐crystal diamond detectors have resolved the nanosecond‐scale pulse structures of both the NSLS and the APS. Prototype single‐crystal quadrant detectors have provided the ability to simultaneously resolve the X‐ray beam position and obtain a quantitative measurement of the flux. 相似文献
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Dr. Christopher J. Smedley Dr. Marie-Claire Giel Dr. Thomas Fallon Prof. Dr. John E. Moses 《Angewandte Chemie (International ed. in English)》2023,62(30):e202303916
We present the synthesis of 1,1-bis(fluorosulfonyl)-2-(pyridin-1-ium-1-yl)ethan-1-ide, a bench-stable precursor to ethene-1,1-disulfonyl difluoride (EDSF). The novel SuFEx reagent, EDSF, is demonstrated in the preparation of 26 unique 1,1-bissulfonylfluoride substituted cyclobutenes via a cycloaddition reaction. The regioselective click cycloaddition reaction is rapid, straightforward, and highly efficient, enabling the generation of highly functionalized 4-membered ring (4MR) carbocycles. These carbocycles are valuable structural motifs found in numerous bioactive natural products and pharmaceutically relevant small molecules. Additionally, we showcase diversification of the novel cyclobutene cores through selective Cs2CO3-activated SuFEx click chemistry between a single S−F group and an aryl alcohol, yielding the corresponding sulfonate ester products with high efficiency. Finally, density functional theory calculations offer mechanistic insights about the reaction pathway. 相似文献
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