Synthesis of Dibenzoazulene Derivatives via Pd‐Catalyzed (3+2) Alkyne Annulation of Dibenzosuberenone

Abstract Non‐benzenoid PAHs with pentagon/heptagon pairs have unique electronic structures and promising opto‐electronic properties. However, the construction of pentagon/heptagon pair units in these PAHs is challenging. Herein, we developed a Pd‐catalyzed (3+2) alkyne annulation reaction of heptagons, and constructed heptagon/pentagon pairs. The substrate scope is wide and the yield is good to moderate. A series of dibenzoauzlene derivatives were synthesized and their opto‐electronic properties were systematically studied by UV‐vis absorption and cyclic voltammetry. In addition, the dibenzoazulene derivative was further transformed to tropylium cation and tropyl radical, which showed bathochromic shifted absorption and switched aromaticity.

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Publication Details

Journal
ChemCatChem
Published
2024-10-26
DOI
https://doi.org/10.1002/cctc.202401310
Citations
2
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.50

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article

Synthesis of Dibenzoazulene Derivatives via Pd‐Catalyzed (3+2) Alkyne Annulation of Dibenzosuberenone

Liyuan Qin, Xi‐Sha Zhang, Junlong Ma, Zhichun Shangguan et al.
2 citations
ChemCatChem
Catalytic C–H Functionalization Methods
0.50
article

Synthesis of Dibenzoazulene Derivatives via Pd‐Catalyzed (3+2) Alkyne Annulation of Dibenzosuberenone

Liyuan Qin, Xi‐Sha Zhang, Junlong Ma, Zhichun Shangguan, Yilin Shu, Zhuangzhuang Ma, Zheng Duan, Liang Qi, Cheng Li, Deqing Zhang
article en
2 citations

Abstract

Abstract Non‐benzenoid PAHs with pentagon/heptagon pairs have unique electronic structures and promising opto‐electronic properties. However, the construction of pentagon/heptagon pair units in these PAHs is challenging. Herein, we developed a Pd‐catalyzed (3+2) alkyne annulation reaction of heptagons, and constructed heptagon/pentagon pairs. The substrate scope is wide and the yield is good to moderate. A series of dibenzoauzlene derivatives were synthesized and their opto‐electronic properties were systematically studied by UV‐vis absorption and cyclic voltammetry. In addition, the dibenzoazulene derivative was further transformed to tropylium cation and tropyl radical, which showed bathochromic shifted absorption and switched aromaticity.

ChemCatChemVol. 16(23)
Chinese Academy of Sciences (CN), Zhengzhou University (CN), Beijing National Laboratory for Molecular Sciences (CN), Institute of Chemistry (CN), University of Chinese Academy of Sciences (CN), Lanzhou University (CN)
National Natural Science Foundation of China, Chinese Academy of Sciences, Youth Innovation Promotion Association of the Chinese Academy of Sciences, CAS-Croucher Funding Scheme for Joint Laboratories, Beijing Municipal Natural Science Foundation
Clean water and sanitation
Openalex Percentile: Top 38%
Catalytic C–H Functionalization Methods
0.50
DOISourceOpenAlex
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