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Thiophene-fused ladder boroles with high antiaromaticity
Azusa Iida1, Shigehiro Yamaguchi
1Department of Chemistry, Graduate School of Science, Nagoya University and JST-CREST, Furo, Chikusa, Nagoya 464-8602, Japan.
Abstract:
A series of polycyclic thiophene-fused boroles were synthesized on the basis of stepwise substitution reactions from thienylboronic ester precursors. In these ladder-type π-conjugated systems, the thiophene-fused structure enhances the antiaromaticity of the borole ring. This trend is opposite to the conventional understanding that the arene-fused structure decreases the antiaromaticity of the 4π-electron ring skeletons. The ladder boroles exhibited characteristic properties such as long-wavelength absorptions and low reduction potentials.
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