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Step-saving synthesis of star-shaped hole-transporting materials with carbazole or phenothiazine cores via optimized C–H/C–Br coupling reactions

In most research papers, synthesis of organic hole-transporting materials relies on a key-reaction: Stille cross-couplings. This requires tedious prefunctionalizations including the preparation and treatment of unstable organolithium and toxicity-concern organotin reagents. In contrast to traditiona...

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Autores principales: Chen, Jui-Heng, Lee, Kun-Mu, Ting, Chang-Chieh, Liu, Ching-Yuan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8695233/
https://www.ncbi.nlm.nih.gov/pubmed/35423386
http://dx.doi.org/10.1039/d0ra10190g
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author Chen, Jui-Heng
Lee, Kun-Mu
Ting, Chang-Chieh
Liu, Ching-Yuan
author_facet Chen, Jui-Heng
Lee, Kun-Mu
Ting, Chang-Chieh
Liu, Ching-Yuan
author_sort Chen, Jui-Heng
collection PubMed
description In most research papers, synthesis of organic hole-transporting materials relies on a key-reaction: Stille cross-couplings. This requires tedious prefunctionalizations including the preparation and treatment of unstable organolithium and toxicity-concern organotin reagents. In contrast to traditional multistep synthesis, this work describes that a series of star-shaped small molecules with a carbazole or phenothiazine core can be efficiently synthesized through a shortcut using optimized direct C–H/C–Br cross-couplings as the key step, thus avoiding dealing with the highly reactive organolithium or the toxic organotin species. Device fabrication of perovskite solar cells employing these molecules (6–13) as hole-transporting layers exhibit promising power conversion efficiencies of up to 17.57%.
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spelling pubmed-86952332022-04-13 Step-saving synthesis of star-shaped hole-transporting materials with carbazole or phenothiazine cores via optimized C–H/C–Br coupling reactions Chen, Jui-Heng Lee, Kun-Mu Ting, Chang-Chieh Liu, Ching-Yuan RSC Adv Chemistry In most research papers, synthesis of organic hole-transporting materials relies on a key-reaction: Stille cross-couplings. This requires tedious prefunctionalizations including the preparation and treatment of unstable organolithium and toxicity-concern organotin reagents. In contrast to traditional multistep synthesis, this work describes that a series of star-shaped small molecules with a carbazole or phenothiazine core can be efficiently synthesized through a shortcut using optimized direct C–H/C–Br cross-couplings as the key step, thus avoiding dealing with the highly reactive organolithium or the toxic organotin species. Device fabrication of perovskite solar cells employing these molecules (6–13) as hole-transporting layers exhibit promising power conversion efficiencies of up to 17.57%. The Royal Society of Chemistry 2021-02-26 /pmc/articles/PMC8695233/ /pubmed/35423386 http://dx.doi.org/10.1039/d0ra10190g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Chen, Jui-Heng
Lee, Kun-Mu
Ting, Chang-Chieh
Liu, Ching-Yuan
Step-saving synthesis of star-shaped hole-transporting materials with carbazole or phenothiazine cores via optimized C–H/C–Br coupling reactions
title Step-saving synthesis of star-shaped hole-transporting materials with carbazole or phenothiazine cores via optimized C–H/C–Br coupling reactions
title_full Step-saving synthesis of star-shaped hole-transporting materials with carbazole or phenothiazine cores via optimized C–H/C–Br coupling reactions
title_fullStr Step-saving synthesis of star-shaped hole-transporting materials with carbazole or phenothiazine cores via optimized C–H/C–Br coupling reactions
title_full_unstemmed Step-saving synthesis of star-shaped hole-transporting materials with carbazole or phenothiazine cores via optimized C–H/C–Br coupling reactions
title_short Step-saving synthesis of star-shaped hole-transporting materials with carbazole or phenothiazine cores via optimized C–H/C–Br coupling reactions
title_sort step-saving synthesis of star-shaped hole-transporting materials with carbazole or phenothiazine cores via optimized c–h/c–br coupling reactions
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8695233/
https://www.ncbi.nlm.nih.gov/pubmed/35423386
http://dx.doi.org/10.1039/d0ra10190g
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