Functionalization of biphenylcarbazole (CBP) with siloxane-hybrid chains for solvent-free liquid materials

Funding: This research was funded by the French National Research Agency (ANR) through the Programme d’Investissement d’Avenir under contract ANR-11-LABX-0058-NIE within the Investissement d’Avenir program ANR-10-IDEX-0002-02 and was supported by Khalifa University through the grant RC2-2018-024.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.Peer reviewe

Control of the organization of 4,4′-bis(carbazole)-1,1′-biphenyl (CBP) molecular materials through siloxane functionalization

Funding: This research was funded by the French National Research Agency (ANR) through the Programme d’Investissement d’Avenir under contract ANR-11-LABX-0058-NIE within the Investissement d’Avenir program ANR-10-IDEX-0002-02.We show that through the introduction of short dimethylsiloxane chains, it was possible to suppress the crystalline state of CBP in favor of various types of organization, transitioning from a soft crystal to a fluid liquid crystal mesophase, then to a liquid state. Characterized by X-ray scattering, all organizations reveal a similar layered configuration in which layers of edge-on lying CBP cores alternate with siloxane. The difference between all CBP organizations essentially lay on the regularity of the molecular packing that modulates the interactions of neighboring conjugated cores. As a result, the materials show quite different thin film absorption and emission properties, which could be correlated to the features of the chemical architectures and the molecular organizations.Peer reviewe

Functionalization of micro-size garnet at the end of optical fiber for magneto-optical applications

We utilized a metal propionate solution to prepare polycrystalline bismuth-substituted yttrium iron garnets through the metal-organic decomposition process. After conducting thorough optimization, we successfully synthesized a garnet that exhibited a high magneto-optic response directly at the end of an optical fiber. A notable achievement of our work lies in the ability to restrict the size and position of the garnet to match the dimensions of the fiber's core. The functionalized fiber was integrated into a magneto-optical sensor setup, offering the flexibility to operate either in the Faraday rotation or magnetic circular dichroism mode

Functionalization of Biphenylcarbazole (CBP) with Siloxane-Hybrid Chains for Solvent-Free Liquid Materials

International audienceWe 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 application

Control of the Organization of 4,4′-bis(carbazole)-1,1′-biphenyl (CBP) Molecular Materials through Siloxane Functionalization

International audienceWe show that through the introduction of short dimethylsiloxane chains, it was possible to suppress the crystalline state of CBP in favor of various types of organization, transitioning from a soft crystal to a fluid liquid crystal mesophase, then to a liquid state. Characterized by X-ray scattering, all organizations reveal a similar layered configuration in which layers of edge-on lying CBP cores alternate with siloxane. The difference between all CBP organizations essentially lay on the regularity of the molecular packing that modulates the interactions of neighboring conjugated cores. As a result, the materials show quite different thin film absorption and emission properties, which could be correlated to the features of the chemical architectures and the molecular organizations