Citation: Li Linan, Gao Ying, Dou Chuandong, Liu Jun. B←N-containing azaacenes with propynyl groups on boron atoms[J]. Chinese Chemical Letters, ;2020, 31(5): 1193-1196. doi: 10.1016/j.cclet.2019.11.018 shu

B←N-containing azaacenes with propynyl groups on boron atoms

Li Linan ^a ,
Gao Ying ^a,*, ,
Dou Chuandong ^b,*, ,
Liu Jun ^b,*,

a.
School of Chemistry and Environmental Engineering, Changchun University of Science and Technology, Changchun 130022, China
b.
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China

gaoying@cust.edu.cn

chuandong.dou@ciac.ac.cn

liujun@ciac.ac.cn

Received Date: 26 September 2019
Revised Date: 2 November 2019
Accepted Date: 11 November 2019
Available Online: 12 November 2019

Figures(4)

For organnoboron compounds, the substituents on boron atoms are very important because they not only impact on the molecular stability but also significantly modulate the electronic structures and properties. In this manuscript, we synthesized two new B←N-containing azaacenes with propynyl groups on boron atoms through one-step Grignard reaction. Replacing fluorine atoms by propynyl groups greatly impacts on the electronic energy levels, especially enhancing the HOMO levels, thus leading to the narrowed HOMO-LUMO bandgaps. These B←N-containing azaacenes exhibit the NIR light-absorption (λ_abs=706 nm for 2a and 762 nm for 2b) and fluorescence properties (λ_em=740 nm for 2a and 802 nm for 2b), as well as multiple reversible redox behaviors, which are significantly different from the analogs with fluorine atoms. This study thus provides a functional substituent of boron atom, which may lead to new organoboron materials with fascinating properties.
- Polyarene,
- Azaacene,
- B-N coordination bond,
- NIR absorption,
- Fluorescence
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