A Stable Saddle-Shaped Polycyclic Hydrocarbon with an Open-Shell Singlet Ground State
Ji Ma
Center for Advancing Electronics Dresden (cfaed), Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorCorresponding Author
Dr. Junzhi Liu
Center for Advancing Electronics Dresden (cfaed), Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorProf. Dr. Martin Baumgarten
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
Search for more papers by this authorYubin Fu
Center for Advancing Electronics Dresden (cfaed), Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorProf. Dr. Yuan-Zhi Tan
State Key Laboratory of Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, 361005 Xiamen, China
Search for more papers by this authorKarl Sebastian Schellhammer
Institute for Materials Science, Max Bergmann Center of Biomaterials, Dresden Center for Computational Materials Science, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorDr. Frank Ortmann
Institute for Materials Science, Max Bergmann Center of Biomaterials, Dresden Center for Computational Materials Science, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorProf. Dr. Gianaurelio Cuniberti
Institute for Materials Science, Max Bergmann Center of Biomaterials, Dresden Center for Computational Materials Science, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorDr. Hartmut Komber
Leibniz-Institut für Polymerforschung Dresden e. V., Hohe Strasse 6, 01069 Dresden, Germany
Search for more papers by this authorDr. Reinhard Berger
Center for Advancing Electronics Dresden (cfaed), Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorProf. Dr. Klaus Müllen
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Xinliang Feng
Center for Advancing Electronics Dresden (cfaed), Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorJi Ma
Center for Advancing Electronics Dresden (cfaed), Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorCorresponding Author
Dr. Junzhi Liu
Center for Advancing Electronics Dresden (cfaed), Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorProf. Dr. Martin Baumgarten
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
Search for more papers by this authorYubin Fu
Center for Advancing Electronics Dresden (cfaed), Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorProf. Dr. Yuan-Zhi Tan
State Key Laboratory of Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, 361005 Xiamen, China
Search for more papers by this authorKarl Sebastian Schellhammer
Institute for Materials Science, Max Bergmann Center of Biomaterials, Dresden Center for Computational Materials Science, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorDr. Frank Ortmann
Institute for Materials Science, Max Bergmann Center of Biomaterials, Dresden Center for Computational Materials Science, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorProf. Dr. Gianaurelio Cuniberti
Institute for Materials Science, Max Bergmann Center of Biomaterials, Dresden Center for Computational Materials Science, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorDr. Hartmut Komber
Leibniz-Institut für Polymerforschung Dresden e. V., Hohe Strasse 6, 01069 Dresden, Germany
Search for more papers by this authorDr. Reinhard Berger
Center for Advancing Electronics Dresden (cfaed), Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorProf. Dr. Klaus Müllen
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Xinliang Feng
Center for Advancing Electronics Dresden (cfaed), Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
Search for more papers by this authorGraphical Abstract
Stay in the saddle: A curved polycyclic hydrocarbon synthesized by extending the twisted bischrysene core by two indene units displayed a stable singlet biradical structure in the ground state. X-ray crystallographic analysis clearly revealed its saddle-shaped conformation.
Abstract
Diindeno-fused bischrysene, a new diindeno-based polycyclic hydrocarbon (PH), was synthesized and characterized. It was elucidated in detailed experimental and theoretical studies that this cyclopenta-fused PH possesses an open-shell singlet biradical structure in the ground state and exhibits high stability under ambient conditions (t1/2=39 days). The crystal structure unambiguously shows a novel saddle-shaped π-conjugated carbon skeleton due to the steric hindrance of the central cove-edged bischrysene unit. UV/Vis spectral measurements revealed that the title molecule has a very narrow optical energy gap of 0.92 eV, which is consistent with the electrochemical analysis and further supported by density functional theory (DFT) calculations.
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Citing Literature
March 13, 2017
Pages 3280-3284
