Polycyclic π-electron system with boron at its center

J Am Chem Soc. 2012 Jun 6;134(22):9130-3. doi: 10.1021/ja3036042. Epub 2012 May 21.

Abstract

We disclose a new planarized triarylborane in which the tri-coordinated boron atom is embedded in a fully fused polycyclic π-conjugated skeleton. The compound shows high stability toward oxygen, water, and silica gel, despite the absence of steric protection around the B atom. Reflecting the electron-donating character of the π-skeleton and the electron-accepting character of the B atom, this compound shows broad absorption bands that cover the entire visible region and a fluorescence in the visible/near-IR region. In addition, this compound shows dramatic property changes upon formation of a tetra-coordinated borate, such as thermochromic behavior in the presence of pyridine.