A Stable Saddle-Shaped Polycyclic Hydrocarbon with an Open-Shell Singlet Ground State
Angewandte Chemie International Edition 12, 3280-3284 (2017).
J. Ma, J. Liu, M. Baumgarten, Y. Fu, Y. Z. Tan, K. S. Schellhammer, F. Ortmann, G. Cuniberti, H. Komber, R. Berger, K. Müllen, and X. Feng.
https://doi.org/10.1002/anie.201611689

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 (t(1/2) = 39 days). The crystal structure unambiguously shows a novel saddle-shaped pi-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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A Stable Saddle-Shaped Polycyclic Hydrocarbon with an Open-Shell Singlet Ground State
Angewandte Chemie International Edition 12, 3280-3284 (2017).
J. Ma, J. Liu, M. Baumgarten, Y. Fu, Y. Z. Tan, K. S. Schellhammer, F. Ortmann, G. Cuniberti, H. Komber, R. Berger, K. Müllen, and X. Feng.
https://doi.org/10.1002/anie.201611689

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 (t(1/2) = 39 days). The crystal structure unambiguously shows a novel saddle-shaped pi-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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Involved Scientists