Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation
The development of long-wavelength photoinduced copper-catalyzed azide–alkyne click (CuAAC) reaction routes is attractive for organic and polymer chemistry. In this study, we present a novel synthetic methodology for the photoinduced CuAAC reaction utilizing exfoliated two-dimensional (2D) few-layer...
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doaj-bf782af8b52045659aab3a0fb5c5a1fd2021-10-05T13:40:35ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-09-011712477248710.3762/bjoc.17.1641860-5397-17-164Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiationAzra Kocaarslan0Zafer Eroglu1Önder Metin2Yusuf Yagci3Department of Chemistry, Istanbul Technical University, Maslak, 34469 Istanbul, TurkeyDepartment of Chemistry, Koç University, Sarıyer, 34450, Istanbul, TurkeyDepartment of Chemistry, Koç University, Sarıyer, 34450, Istanbul, TurkeyDepartment of Chemistry, Istanbul Technical University, Maslak, 34469 Istanbul, TurkeyThe development of long-wavelength photoinduced copper-catalyzed azide–alkyne click (CuAAC) reaction routes is attractive for organic and polymer chemistry. In this study, we present a novel synthetic methodology for the photoinduced CuAAC reaction utilizing exfoliated two-dimensional (2D) few-layer black phosphorus nanosheets (BPNs) as photocatalysts under white LED and near-IR (NIR) light irradiation. Upon irradiation, BPNs generated excited electrons and holes on its conduction (CB) and valence band (VB), respectively. The excited electrons thus formed were then transferred to the CuII ions to produce active CuI catalysts. The ability of BPNs to initiate the CuAAC reaction was investigated by studying the reaction between various low molar mass alkyne and azide derivatives under both white LED and NIR light irradiation. Due to its deeper penetration of NIR light, the possibility of synthesizing different macromolecular structures such as functional polymers, cross-linked networks and block copolymer has also been demonstrated. The structural and molecular properties of the intermediates and final products were evaluated by spectral and chromatographic analyses.https://doi.org/10.3762/bjoc.17.164black phosphorusclick chemistryheterogeneous photocatalystnear infraredphosphorene |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Azra Kocaarslan Zafer Eroglu Önder Metin Yusuf Yagci |
spellingShingle |
Azra Kocaarslan Zafer Eroglu Önder Metin Yusuf Yagci Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation Beilstein Journal of Organic Chemistry black phosphorus click chemistry heterogeneous photocatalyst near infrared phosphorene |
author_facet |
Azra Kocaarslan Zafer Eroglu Önder Metin Yusuf Yagci |
author_sort |
Azra Kocaarslan |
title |
Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation |
title_short |
Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation |
title_full |
Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation |
title_fullStr |
Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation |
title_full_unstemmed |
Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation |
title_sort |
exfoliated black phosphorous-mediated cuaac chemistry for organic and macromolecular synthesis under white led and near-ir irradiation |
publisher |
Beilstein-Institut |
series |
Beilstein Journal of Organic Chemistry |
issn |
1860-5397 |
publishDate |
2021-09-01 |
description |
The development of long-wavelength photoinduced copper-catalyzed azide–alkyne click (CuAAC) reaction routes is attractive for organic and polymer chemistry. In this study, we present a novel synthetic methodology for the photoinduced CuAAC reaction utilizing exfoliated two-dimensional (2D) few-layer black phosphorus nanosheets (BPNs) as photocatalysts under white LED and near-IR (NIR) light irradiation. Upon irradiation, BPNs generated excited electrons and holes on its conduction (CB) and valence band (VB), respectively. The excited electrons thus formed were then transferred to the CuII ions to produce active CuI catalysts. The ability of BPNs to initiate the CuAAC reaction was investigated by studying the reaction between various low molar mass alkyne and azide derivatives under both white LED and NIR light irradiation. Due to its deeper penetration of NIR light, the possibility of synthesizing different macromolecular structures such as functional polymers, cross-linked networks and block copolymer has also been demonstrated. The structural and molecular properties of the intermediates and final products were evaluated by spectral and chromatographic analyses. |
topic |
black phosphorus click chemistry heterogeneous photocatalyst near infrared phosphorene |
url |
https://doi.org/10.3762/bjoc.17.164 |
work_keys_str_mv |
AT azrakocaarslan exfoliatedblackphosphorousmediatedcuaacchemistryfororganicandmacromolecularsynthesisunderwhiteledandnearirirradiation AT zafereroglu exfoliatedblackphosphorousmediatedcuaacchemistryfororganicandmacromolecularsynthesisunderwhiteledandnearirirradiation AT ondermetin exfoliatedblackphosphorousmediatedcuaacchemistryfororganicandmacromolecularsynthesisunderwhiteledandnearirirradiation AT yusufyagci exfoliatedblackphosphorousmediatedcuaacchemistryfororganicandmacromolecularsynthesisunderwhiteledandnearirirradiation |
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1716841849664045056 |