Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 18, Pages 6952-6955Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2019977
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan [19675001]
- CREST, JST
- JSPS
- Grants-in-Aid for Scientific Research [19675001, 09J03775] Funding Source: KAKEN
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A series of polycyclic thiophene-fused boroles were synthesized on the basis of stepwise substitution reactions from thienylboronic ester precursors. In these ladder-type pi-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 4 pi-electron ring skeletons. The ladder boroles exhibited characteristic properties such as long-wavelength absorptions and low reduction potentials.
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