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Abstract
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.
Highlights
Siloxane-containing organic materials are widely used and have currently become essential for many sectors of activities such as cosmetics, paints, coatings, packaging as well as automotive, household and medical appliances
From a synthetic point of view, the introduction of a siloxane chain to a compound of interest usually requires starting the synthesis from the beginning
The addition of alkenyl linkers for introducing siloxane chains to these conjugated cores, those activated with heteroatoms such as carbazoles brings elevated complexity due to unfavored side reactions [21,22]
Summary
Siloxane-containing organic materials are widely used and have currently become essential for many sectors of activities such as cosmetics, paints, coatings, packaging as well as automotive, household and medical appliances. The incorporation of short siloxane segments into electroactive conjugated species enables a valuable improvement of the organization, thermal and mechanical properties of the materials. Siloxane-hybrid side-chain conjugated polymers have been reported to exhibit lamellar mesomorphic organization with enhanced charge transport properties [11,12,13,14]. This effect was attributed to the singular fluid and segregating character of siloxane chains that impose a better facing of the polymers with improved π-stacking overlap [14]. Siloxanechain functionalization appears as an excellent alternative to classical branched alkyl chain functionalization for designing solvent-free functional molecular liquids (FMLs) [4,15,16]
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