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231226s2022 xx |||||o 00| ||eng c |
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|a 10.1021/acs.langmuir.2c00100
|2 doi
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|a pubmed24n1133.xml
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|a (DE-627)NLM339997125
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|a (NLM)35470670
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|a DE-627
|b ger
|c DE-627
|e rakwb
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|a eng
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| 100 |
1 |
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|a Li, Tiexin
|e verfasserin
|4 aut
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| 245 |
1 |
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|a On-Surface Azide-Alkyne Cycloaddition Reaction
|b Does It Click with Ruthenium Catalysts?
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|c 2022
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| 336 |
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|a Text
|b txt
|2 rdacontent
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|a ƒaComputermedien
|b c
|2 rdamedia
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|a ƒa Online-Ressource
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|2 rdacarrier
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|a Date Revised 01.11.2023
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|a published: Print-Electronic
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|a Citation Status PubMed-not-MEDLINE
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|a Owing to its simplicity, selectivity, high yield, and the absence of byproducts, the "click" azide-alkyne reaction is widely used in many areas. The reaction is usually catalyzed by copper(I), which selectively produces the 1,4-disubstituted 1,2,3-triazole regioisomer. Ruthenium-based catalysts were later developed to selectively produce the opposite regioselectivity─the 1,5-disubstituted 1,2,3-triazole isomer. Ruthenium-based catalysis, however, remains only tested for click reactions in solution, and the suitability of ruthenium catalysts for surface-based click reactions remains unknown. Also unknown are the electrical properties of the 1,4- and 1,5-regioisomers, and to measure them, both isomers need to be assembled on the electrode surface. Here, we test whether ruthenium catalysts can be used to catalyze surface azide-alkyne reactions to produce 1,5-disubstituted 1,2,3-triazole, and compare their electrochemical properties, in terms of surface coverages and electron transfer kinetics, to those of the compound formed by copper catalysis, 1,4-disubstituted 1,2,3-triazole isomer. Results show that ruthenium(II) complexes catalyze the click reaction on surfaces yielding the 1,5-disubstituted isomer, but the rate of the reaction is remarkably slower than that of the copper-catalyzed reaction, and this is related to the size of the catalyst involved as an intermediate in the reaction. The electron transfer rate constant (ket) for the ruthenium-catalyzed reaction is 30% of that measured for the copper-catalyzed 1,4-isomer. The lower conductivity of the 1,5-isomer is confirmed by performing nonequilibrium Green's function computations on relevant model systems. These findings demonstrate the feasibility of ruthenium-based catalysis of surface click reactions and point toward an electrical method for detecting the isomers of click reactions
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|a Journal Article
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1 |
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|a Dief, Essam M
|e verfasserin
|4 aut
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1 |
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|a Kalužná, Zlatica
|e verfasserin
|4 aut
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| 700 |
1 |
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|a MacGregor, Melanie
|e verfasserin
|4 aut
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1 |
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|a Foroutan-Nejad, Cina
|e verfasserin
|4 aut
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| 700 |
1 |
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|a Darwish, Nadim
|e verfasserin
|4 aut
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| 773 |
0 |
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|i Enthalten in
|t Langmuir : the ACS journal of surfaces and colloids
|d 1992
|g 38(2022), 18 vom: 10. Mai, Seite 5532-5541
|w (DE-627)NLM098181009
|x 1520-5827
|7 nnns
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| 773 |
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|g volume:38
|g year:2022
|g number:18
|g day:10
|g month:05
|g pages:5532-5541
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|u http://dx.doi.org/10.1021/acs.langmuir.2c00100
|3 Volltext
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|a GBV_ILN_22
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|a GBV_ILN_721
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|a AR
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|d 38
|j 2022
|e 18
|b 10
|c 05
|h 5532-5541
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