Citation: Bo Yu, Pengchen Du, Jianwen Guo, Hanshen Xin, Jianhua Zhang. Nonalternant isomer of pentacene fusing two azulene units[J]. Chinese Chemical Letters, ;2024, 35(5): 109321. doi: 10.1016/j.cclet.2023.109321 shu

Nonalternant isomer of pentacene fusing two azulene units

Bo Yu ^{a, b} ,
Pengchen Du ^b ,
Jianwen Guo ^b ,
Hanshen Xin ^{a, b, *,} ,
Jianhua Zhang ^{a, b, *,}

a.
Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444, China
b.
School of Microelectronics, Shanghai University, Shanghai 201800, China

xinhanshen@shu.edu.cn

jhzhang@oa.shu.edu.cn

Received Date: 7 September 2023
Revised Date: 14 November 2023
Accepted Date: 17 November 2023
Available Online: 19 November 2023

Figures(6)

Azulene is a promising building block for creating innovative polycyclic aromatic hydrocarbons. This study involved the construction of three nonalternant isomers of pentacene by fusing two azulene units, named Az-PH1/2/3. Az-PH1 was initially developed through the rhodium(II)-catalyzed cyclization of bis(N-tosylhydrazone)s. Intriguingly, Az-PH1 was also unexpectedly obtained during a nickel(0)-catalyzed one-step tandem reaction. We investigated the optical and electrochemical properties, aromaticity, and photo-oxidative stability of Az-PH1, comparing it with the well-known pentacene using density functional theory, electrochemical, and photophysical tests. Our results showed that the azulene-fusing strategy resulted in a molecule with narrow optical bandgaps (2.046 eV) and a long half-life time under ambient air conditions.
- Azulene,
- Isomer,
- Polycyclic aromatic hydrocarbon,
- Nickel(0)-catalyzed,
- Photo-oxidative stability
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