Carboron is a novel chain polyacetylenic compound exclusively developed by Professor Xia Haiping’s research group at Xiamen University (Figure 1). This discovery marks a significant advancement in the synthesis of metallopentynes and metallopentenes, providing a one-pot synthesis method that enhances efficiency and expands application potential.
Figure 1. General structural formula of Carbon Dragon series products
Figure 2. One-pot synthesis of metallopenteryne and metallopenterene with different metal centers [3]
Figure 3. Carboron is used for the one-step synthesis of ruthenium pentayne [2]
Revolutionizing Metallopentarenes Synthesis
Metallopenterynes and metallopenterenes are part of a new class of aromatic compounds. Previously, synthesizing these materials required complex multi-step reactions, with the metal center restricted to osmium (Os). However, the Carboron series compounds leverage the strong coordination of carbon bonds to enable a one-step synthesis of metallopentynes and metallopentenes with diverse metal centers (Figures 2, 3).
This innovation achieves a direct transformation from anti-aromatic to aromatic structures, establishing a new aromatic system and broadening the scope of organometallic chemistry [1, 2].
Figure 4. As the aromatic size of carbonron compounds increases, the absorption spectrum red-shifts.
Key Structural and Functional Advantages:
- Propargyl Alcohol and Diyne Units:
- Serve as versatile carbon polydentate ligand precursors.
- Enable the development of new synthetic methodologies in organic chemistry.
- Enhanced Optical Properties:
- Aggregation-induced luminescence (AIE) increases as the aromatic structure grows.
- Red-shifted absorption spectra (Figure 4) make the compounds suitable for photoacoustic imaging (PAI) and photothermal therapy [4].
- High Atomic Economy & Sustainability:
- One-step synthesis reduces experimental steps and boosts efficiency.
- Environmentally friendly and resource-efficient processes.
Versatile Applications in Chemistry & Medicine
The ability to prepare heteropentynes and heteropentenes with various metal centers in one step opens up exciting possibilities in:
- Medicinal Chemistry: Targeted drug delivery and imaging.
- Material Science: Developing next-gen luminescent materials.
- Catalysis: Designing novel catalysts with unique electronic properties.
Reference
- Qingde Zhuo, Jianfeng Lin, Yuhui Hua, Xiaoxi Zhou, Yifan Shao, Shiyan Chen, Zhixin Chen, Jun Zhu, Hong Zhang & Haiping Xia. Nature Communications, 2017, 8, 1912.
- Qingde Zhuo, Hong Zhang, Yuhui Hua, Huijun Kang, Xiaoxi Zhou, Xinlei Lin, Zhixin Chen, Jianfeng Lin, Kaiyue Zhuo, Haiping Xia. Sci. Adv. 2018; 4 : eaat0336.
http://hpxia.xmu.edu.cn/research/carbolong/index.html. - Congqing Zhu and Haiping Xia.Accounts of Chemical Research 2018 51 (7), 1691-1700.
向阳 翟
