| Autor: |
Hiromasa Kikuchi, Kazuaki Oniwa, Yoshinori Yamamoto, Masahiro Terada, Tienan Jin, Zhanqiang Xu, Ming Bao |
| Rok vydání: |
2018 |
| Předmět: |
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| Zdroj: |
Chemistry - A European Journal. 24:9041-9050 |
| ISSN: |
0947-6539 |
| Popis: |
Star-shaped π-extended molecules comprising discotic aromatic cores and peripheral π-conjugated arms have attracted significant attention as diverse optoelectronic materials in terms of their large π-surface, tunable self-assembly, enhanced charge transport and fluorescence, and liquid crystallinity. Although many efforts have been made in the construction of various aromatic discotic cores, a new class of C3 -symmetric star-shaped discotic π-molecules consisting of electron-deficient benzotristhiazole and benzotrisoxazole cores, which are expected to exhibit distinct optoelectronic properties, remains unexplored owing to the unachievable synthetic approaches involved in their synthesis. Herein, we report a novel and highly efficient Pd-catalyzed cyclotrimerization of the functionalized thiazoles or oxazoles for the construction of a new class of discotic molecules of benzotristhiazole and benzotrisoxazole central cores with star-shaped π-conjugated arms. The combination of [Pd2 (dba)3 ]/XPhos (dba=dibenzylideneacetone) catalyst systems with the 4-bromo-substituted thiazole enables the formation of a sufficiently stable thiazole-Pd species that participates in the subsequent C-H arylations consecutively to form the corresponding cyclic trimer products. This new class of star-shaped discotic π-extended products showed tunable energy levels and high fluorescence quantum yields that make them promising candidates for optoelectronic applications. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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