| Autor: |
Adam Matej, Bruno de la Torre, Martin Kotora, Jesús I. Mendieta-Moreno, Pingo Mutombo, Pavel Jelínek, Dana Nachtigalova, Jiri Brabec, Timothée Cadart, Mikuláš Matoušek, Libor Veis, Benjamin Mallada |
| Rok vydání: |
2020 |
| Předmět: |
|
| DOI: |
10.26434/chemrxiv.13455908 |
| Popis: |
Synthesis of polycyclic aromatic hydrocarbons containing various non-benzenoid rings remains a big challenge facing contemporary organic chemistry despite a considerable effort made over the last decades. Herein, we present a novel route, employing on-surface mechanochemistry, to synthesize non-alternant polycyclic aromatic hydrocarbon containing up to four distinct kinds of non-benzenoid rings. We show that the surface-induced mechanical constrains imposed on strained helical reactants play a decisive role leading to the formation of products, energetically unfavorable in solution, with a peculiar ring current stabilizing the aromatic character of the π-conjugated system. Determination of the chemical and electronic structures of the most frequent product reveals its closed-shell character and low band gap. The present study renders a new route for the synthesis of novel non-alternant polycyclic aromatic hydrocarbons or other hydrocarbons not available by traditional approaches of organic chemistry in solution. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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