Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Shaya, Janah, Correia, Gabriel, Heinrich, Benoît, Ribierre, Jean-Charles, Polychronopoulou, Kyriaki, Mager, Loïc, Méry, Stéphane
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
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
_version_ 1784630628393680896
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
work_keys_str_mv AT shayajanah functionalizationofbiphenylcarbazolecbpwithsiloxanehybridchainsforsolventfreeliquidmaterials
AT correiagabriel functionalizationofbiphenylcarbazolecbpwithsiloxanehybridchainsforsolventfreeliquidmaterials
AT heinrichbenoit functionalizationofbiphenylcarbazolecbpwithsiloxanehybridchainsforsolventfreeliquidmaterials
AT ribierrejeancharles functionalizationofbiphenylcarbazolecbpwithsiloxanehybridchainsforsolventfreeliquidmaterials
AT polychronopouloukyriaki functionalizationofbiphenylcarbazolecbpwithsiloxanehybridchainsforsolventfreeliquidmaterials
AT magerloic functionalizationofbiphenylcarbazolecbpwithsiloxanehybridchainsforsolventfreeliquidmaterials
AT merystephane functionalizationofbiphenylcarbazolecbpwithsiloxanehybridchainsforsolventfreeliquidmaterials