Applied Cross-Coupling Reactions by Yasushi Nishihara

Author:Yasushi Nishihara
Language: eng
Format: epub
Publisher: Springer Berlin Heidelberg, Berlin, Heidelberg

Kumada-Tamao-Corriu coupling is a longstanding methodology for the synthesis of oligothiophenes 1 that do not bear electrophilic functional groups, as shown in Scheme 5.1 [14]. Because the obtained products show smectic liquid crystal phases in the range of 98–168 °C, these compounds could be expected to be useful in field-effect transistors (FETs).

Scheme 5.1Synthesis of oligothiophenes 1 by Kumada-Tamao-Corriu coupling

Cheng has synthesized 2,5-diarylated thiophene derivatives with liquid crystalline properties by using a combination of Kumada-Tamao-Corriu and Suzuki–Miyaura couplings (Scheme 5.2) [15]. The synthesized compounds 2 showed nematic phases below 71 (n = 6) and 60 °C (n = 12); however, the liquid crystal phase was not apparent in the case of n = 16. It is suspected that the obtained compounds form monotropic liquid crystals as a result of their bent structures.

Scheme 5.2Synthesized 2,5-diarylated thiophene derivatives

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