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...
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MDPI AG
2021-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/1/89 |
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| author | Janah Shaya Gabriel Correia Benoît Heinrich Jean-Charles Ribierre Kyriaki Polychronopoulou Loïc Mager Stéphane Méry |
| author_facet | Janah Shaya Gabriel Correia Benoît Heinrich Jean-Charles Ribierre Kyriaki Polychronopoulou Loïc Mager Stéphane Méry |
| author_sort | Janah Shaya |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-03-10T03:31:19Z |
| format | Article |
| id | doaj.art-e1933260da8a476e99aa70e0756014c9 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:31:19Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-e1933260da8a476e99aa70e0756014c92023-11-23T11:56:34ZengMDPI AGMolecules1420-30492021-12-012718910.3390/molecules27010089Functionalization of Biphenylcarbazole (CBP) with Siloxane-Hybrid Chains for Solvent-Free Liquid MaterialsJanah Shaya0Gabriel Correia1Benoît Heinrich2Jean-Charles Ribierre3Kyriaki Polychronopoulou4Loïc Mager5Stéphane Méry6IPCMS, CNRS-Strasbourg University, UMR7504, 23 Rue du Loess, BP 43, 67034 Strasbourg, FranceIPCMS, CNRS-Strasbourg University, UMR7504, 23 Rue du Loess, BP 43, 67034 Strasbourg, FranceIPCMS, CNRS-Strasbourg University, UMR7504, 23 Rue du Loess, BP 43, 67034 Strasbourg, FranceCenter for Organic Photonics and Electronics Research (OPERA), Kyushu University, 744 Motooka, Nishi, Fukuoka 819-0395, JapanDepartment of Mechanical Engineering, Khalifa University of Science and Technology, Abu Dhabi P.O. Box 127788, United Arab EmiratesIPCMS, CNRS-Strasbourg University, UMR7504, 23 Rue du Loess, BP 43, 67034 Strasbourg, FranceIPCMS, CNRS-Strasbourg University, UMR7504, 23 Rue du Loess, BP 43, 67034 Strasbourg, FranceWe 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.https://www.mdpi.com/1420-3049/27/1/89molecular liquidallyl isomerizationStille couplingUllmann couplinghydrosilylationliquid optoelectronics |
| spellingShingle | Janah Shaya Gabriel Correia Benoît Heinrich Jean-Charles Ribierre Kyriaki Polychronopoulou Loïc Mager Stéphane Méry Functionalization of Biphenylcarbazole (CBP) with Siloxane-Hybrid Chains for Solvent-Free Liquid Materials Molecules molecular liquid allyl isomerization Stille coupling Ullmann coupling hydrosilylation liquid optoelectronics |
| 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 | molecular liquid allyl isomerization Stille coupling Ullmann coupling hydrosilylation liquid optoelectronics |
| url | https://www.mdpi.com/1420-3049/27/1/89 |
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