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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Main Authors: Azra Kocaarslan, Zafer Eroglu, Önder Metin, Yusuf Yagci
Format: Article
Language:English
Published: Beilstein-Institut 2021-09-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.17.164
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spelling 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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