Merging gold plasmonic nanoparticles and l-proline inside a MOF for plasmon-induced visible light chiral organocatalysis at low temperature

Merging gold plasmonic nanoparticles and l-proline inside a MOF for plasmon-induced visible light chiral organocatalysis at low temperature

Bibliographic Details
Parent link:Nanoscale.— .— Cambridge: RSC Publishing
Vol. 16, iss. 10.— 2024.— P. 5313-5322
Corporate Author: National Research Tomsk Polytechnic University (570)
Other Authors: Kushnarenko A, S, Angelina Sergeevna, Zabelina A. A. Anastasiya Aleksandrovna, Guselnikova O. A. Olga Andreevna, Milyutina (Miliutina) E. V. Elena Vadimovna, Vokata B., Zabelin D, V, Denis Vladimirovich, Burtsev V., Valiev R. R. Rashid Rinatovich, Kolska Zd. Zdenka, Paidar M., Sikora V, Yu. Vadim Yurjevich, Postnikov P. S. Pavel Sergeevich, Svorcik V, Vaclav, Lyutakov O. Oleksy
Summary:Title screen
Light-driven asymmetric photocatalysis represents a straightforward approach in modern organic chemistry. In comparison to the homogeneous one, heterogeneous asymmetric photocatalysis has the advantages of easy catalyst separation, recovery, and reuse, thus being cost- and time-effective. Here, we demonstrate how plasmon-active centers (gold nanoparticles – AuNPs) allow visible light triggering of chiral catalyst (proline) in model aldol reaction between acetone and benzaldehyde. The metal–organic framework UiO-66–NH2 was used as an advanced host platform for the loading of proline and AuNPs and their stabilization in spatial proximity. Aldol reactions were carried out at a low temperature (−20 °C) under light illumination which resulted in 91% ee with a closed-to-quantitative yield, 4.5 times higher than that without light (i.e. in the absence of plasmon triggering). A set of control experiments and quantum chemical modeling revealed that the plasmon assistance proceeds through hot electron excitation followed by an interaction with an enamine with the formation of anion radical species. We also demonstrated the high stability of the proposed system in multiple catalytic cycles without leaching metal ions, which makes our approach especially promising for heterogeneous asymmetric photocatalysis.
Текстовый файл
AM_Agreement
Published: 2024
Subjects:
электронный ресурс
труды учёных ТПУ
Online Access:https://doi.org/10.1039/D3NR04707E
Format: Electronic Book Chapter
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=674377

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