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Functionalization of Biphenylcarbazole (CBP) with Siloxane-Hybrid Chains for Solvent-Free Liquid Materials
We report herein the synthesis of siloxane-functionalized CBP molecules (4,4′-bis(carbazole)-1,1′-biphenyl) for liquid optoelectronic applications. The room-temperature liquid state is obtained through a convenient functionalization of the molecules with heptamethyltrisiloxane chains via hydrosilyla...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8746609/ https://www.ncbi.nlm.nih.gov/pubmed/35011322 http://dx.doi.org/10.3390/molecules27010089 |
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author | Shaya, Janah Correia, Gabriel Heinrich, Benoît Ribierre, Jean-Charles Polychronopoulou, Kyriaki Mager, Loïc Méry, Stéphane |
author_facet | Shaya, Janah Correia, Gabriel Heinrich, Benoît Ribierre, Jean-Charles Polychronopoulou, Kyriaki Mager, Loïc Méry, Stéphane |
author_sort | Shaya, Janah |
collection | PubMed |
description | We report herein the synthesis of siloxane-functionalized CBP molecules (4,4′-bis(carbazole)-1,1′-biphenyl) for liquid optoelectronic applications. The room-temperature liquid state is obtained through a convenient functionalization of the molecules with heptamethyltrisiloxane chains via hydrosilylation of alkenyl spacers. The synthesis comprises screening of metal-catalyzed methodologies to introduce alkenyl linkers into carbazoles (Stille and Suzuki Miyaura cross-couplings), incorporate the alkenylcarbazoles to dihalobiphenyls (Ullmann coupling), and finally introduce the siloxane chains. The used conditions allowed the synthesis of the target compounds, despite the high reactivity of the alkenyl moieties bound to π-conjugated systems toward undesired side reactions such as polymerization, isomerization, and hydrogenation. The features of these solvent-free liquid CBP derivatives make them potentially interesting for fluidic optoelectronic applications. |
format | Online Article Text |
id | pubmed-8746609 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-87466092022-01-11 Functionalization of Biphenylcarbazole (CBP) with Siloxane-Hybrid Chains for Solvent-Free Liquid Materials Shaya, Janah Correia, Gabriel Heinrich, Benoît Ribierre, Jean-Charles Polychronopoulou, Kyriaki Mager, Loïc Méry, Stéphane Molecules Article We report herein the synthesis of siloxane-functionalized CBP molecules (4,4′-bis(carbazole)-1,1′-biphenyl) for liquid optoelectronic applications. The room-temperature liquid state is obtained through a convenient functionalization of the molecules with heptamethyltrisiloxane chains via hydrosilylation of alkenyl spacers. The synthesis comprises screening of metal-catalyzed methodologies to introduce alkenyl linkers into carbazoles (Stille and Suzuki Miyaura cross-couplings), incorporate the alkenylcarbazoles to dihalobiphenyls (Ullmann coupling), and finally introduce the siloxane chains. The used conditions allowed the synthesis of the target compounds, despite the high reactivity of the alkenyl moieties bound to π-conjugated systems toward undesired side reactions such as polymerization, isomerization, and hydrogenation. The features of these solvent-free liquid CBP derivatives make them potentially interesting for fluidic optoelectronic applications. MDPI 2021-12-24 /pmc/articles/PMC8746609/ /pubmed/35011322 http://dx.doi.org/10.3390/molecules27010089 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Shaya, Janah Correia, Gabriel Heinrich, Benoît Ribierre, Jean-Charles Polychronopoulou, Kyriaki Mager, Loïc Méry, Stéphane Functionalization of Biphenylcarbazole (CBP) with Siloxane-Hybrid Chains for Solvent-Free Liquid Materials |
title | Functionalization of Biphenylcarbazole (CBP) with Siloxane-Hybrid Chains for Solvent-Free Liquid Materials |
title_full | Functionalization of Biphenylcarbazole (CBP) with Siloxane-Hybrid Chains for Solvent-Free Liquid Materials |
title_fullStr | Functionalization of Biphenylcarbazole (CBP) with Siloxane-Hybrid Chains for Solvent-Free Liquid Materials |
title_full_unstemmed | Functionalization of Biphenylcarbazole (CBP) with Siloxane-Hybrid Chains for Solvent-Free Liquid Materials |
title_short | Functionalization of Biphenylcarbazole (CBP) with Siloxane-Hybrid Chains for Solvent-Free Liquid Materials |
title_sort | functionalization of biphenylcarbazole (cbp) with siloxane-hybrid chains for solvent-free liquid materials |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8746609/ https://www.ncbi.nlm.nih.gov/pubmed/35011322 http://dx.doi.org/10.3390/molecules27010089 |
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