Abstract
Star-shaped compounds are widely recognized as emerging materials for optical and electrical applications and as scaffolds of discotic liquid crystal. While the C3-symmetrical tri(phenylthienyl)benzene is the core for several electroopotical materials, no liquid crystal with this scaffold has yet been reported. Acid-catalyzed cyclocondensation of bromoacetylthiophene gives a C3-symmetrical star, threefold Suzuki coupling results in extension of the conjugated system. With 3,4-didodecylocyphenyl boronic acid, a star with a large rigid conjugated system and flexible aliphatic periphery is obtained. Differentials scanning calorimetry and polarized optical microscopy reveal an enantiotropic mesophase from 66 °C to 106 °C.
Highlights
Thiophene is a very prominent building block for the synthesis of organic electronic materials [1,2] and a large variety of oligo- and polythiophenes have been prepared and successfully applied as active material in electronic devices, e.g., OLEDs, OFETs, OVPs and sensors [3,4,5]
Whereas a large number of star-shaped [10,11] and discotic [12,13] π-conjugated systems have been investigated, compounds with a thiophene based core appear only scarcely [13,14]. 1,3,5Tris-(2-thienyl)benzene has been prepared via cyclocondensation of 2-acetylthiophenes [15], a recent approach is based on the addition of benzenetri(methylthiol) to diynes [16]
A few optoelectronic materials based on 1,3,5-trithienylbenzene have been extensively investigated [18,19,20,21,22]
Summary
Thiophene is a very prominent building block for the synthesis of organic electronic materials [1,2] and a large variety of oligo- and polythiophenes have been prepared and successfully applied as active material in electronic devices, e.g., OLEDs, OFETs, OVPs and sensors [3,4,5]. Discotic liquid crystals (DLCs) offer another strategy for orientation and targeted alignment, selfassembly of their large aromatic cores can form conductive columns [7,8,9]. Whereas a large number of star-shaped [10,11] and discotic [12,13] π-conjugated systems have been investigated, compounds with a thiophene based core appear only scarcely [13,14]. A few optoelectronic materials based on 1,3,5-trithienylbenzene have been extensively investigated [18,19,20,21,22]. We report the synthesis of tris(didodecyloxyphenylthienyl)benzene, a π-conjugated star and the first discotic liquid crystal with this core
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