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A Resonating B, N Covalent Bond and Coordination Bond in Aromatic Compounds and Conjugated Polymers
Xingxin Shao1,2, Mengyu Liu1,2, Jun Liu1,2
1State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. China.
Abstract:
We herein report an organoboron compound (SBN-1) based on N-B←N units with a balanced resonance hybrid of B, N single bond (B-N) and B, N coordination bond (B←N). Despite the different chemical environments of the two nitrogen atoms in the N-B←N unit, the single-crystal structure reveals that the two B, N bonds have similar bond lengths of ca. 1.55 Å and are almost equivalent. The resonance nature of the two B, N bonds contributes to the excellent chemical stability and photostability of SBN-1. The N-B←N units in SBN-1 show a strong electron-withdrawing capability and large dipole, resulting in a red-shifted absorption spectrum, downshifted LUMO/HOMO energy levels, and drastically altered molecular packing behaviors in solid state. SBN-1 can be used as a building block to construct small band gap conjugated polymers. The resonance of B, N bonds discovered in this work provides new insight into the design of stable organoboron small molecules and polymers for practical applications.
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