Synthesis and assembly of extended quintulene

Hao Hou, Xin-Jing Zhao, Chun Tang, Yang-Yang Ju, Ze-Ying Deng, Xin-Rong Wang, Liu-Bin Feng, Dong-Hai Lin, Xu Hou, Akimitsu Narita, Klaus Müllen and Yuan-Zhi Tan ()
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Hao Hou: Xiamen University
Xin-Jing Zhao: Xiamen University
Chun Tang: Xiamen University
Yang-Yang Ju: Xiamen University
Ze-Ying Deng: Xiamen University
Xin-Rong Wang: Xiamen University
Liu-Bin Feng: Xiamen University
Dong-Hai Lin: Xiamen University
Xu Hou: Xiamen University
Akimitsu Narita: Max Planck Institute for Polymer Research
Klaus Müllen: Max Planck Institute for Polymer Research
Yuan-Zhi Tan: Xiamen University

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Quintulene, a non-graphitic cycloarene with fivefold symmetry, has remained synthetically elusive due to its high molecular strain originating from its curved structure. Here we report the construction of extended quintulene, which was unambiguously characterized by mass and NMR spectroscopy. The extended quintulene represents a naturally curved nanocarbon based on its conical molecular geometry. It undergoes dimerization in solution via π−π stacking to form a metastable, but isolable bilayer complex. Thermodynamic and kinetic characterization reveals the dimerization process as entropy-driven and following second-order kinetics with a high activation energy. These findings provide a deeper understanding of the assembly of conical nanocarbons. Comparison of optical properties of monomer and dimer points toward a H-type interlayer coupling in the dimer.

Date: 2020
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DOI: 10.1038/s41467-020-17691-7

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