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Synthesis, Intermolecular Interaction, and Semiconductive Behavior of a Delocalized Singlet Biradical Hydrocarbon


  • This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas (No. 17550034, and Area No. 769, Proposal No. 15087202) from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT), Japan.


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A phenalenyl-based Kekulé hydrocarbon with singlet biradical character has been isolated and characterized. Strong intra- and intermolecular interactions between the unpaired electrons lead to short π–π contacts and formation of one-dimensional chains (see picture). Thus, wide valence and conduction bands are established, and the compound shows semiconductive behavior.