Major research fields
Synthetic Organic Chemistry, Materials Chemistry, Computational Chemistry
π-Conjugated molecules are an important class of compounds that are used to produce organic electronics, dyes, sensors, and liquid crystal displays. Incorporation of heteroatoms into a π-conjugated skeleton is a promising way to modulate their physical properties, and thus, intensive efforts have been devoted to the construction of new hetero-π-conjugated frameworks. Because of the lack of a suitable synthetic methodology, only a few π-conjugated molecules with ring junction heteroatoms have been synthesized to date, even though numerous theoretical investigations suggested that those hetero-π-conjugated molecules could be attractive substructures of heteroatom-embedded nanocarbons. Recently, we have developed efficient carbon-heteroatom bond formation reactions, such as hetero Friedel-Crafts reaction, which can provide a facile access to π-conjugated molecules with ring junction heteroatoms. The molecules show attractive physical properties such as fluorescence and charge transport, and can be applied to the field of (opto)electronics. Molecules with such frameworks are not only attractive functional materials but also potential starting compounds for the controlled synthesis of heteroatom-embedded nanocarbons (i.e. heteronanographene) by surface-assisted coupling or amplification sheet growth.
Major relevant publications
- Hirai, H.; Nakajima, K.; Nakatsuka, S.; Shiren, K.; Ni, J.; Nomura, S.; Ikuta, T.; Hatakeyama, T. One-Step Borylation of 1,3-Diaryloxybenzenes Towards Efficient Materials for Organic Light-Emitting Diodes, Angew. Chem., Int. Ed. 54, 13581–13585 (2015).
- Hashimoto, S.; Nakatsuka, S.; Nakamura, M.; Hatakeyama, T. Construction of a Highly Distorted Benzene Ring in a Double Helicene, Angew. Chem., Int. Ed. 53, 14074–14076 (2014).
- Hatakeyama, T.; Hashimoto, S.; Oba, T.; Nakamura, M. Azaboradibenzohelicene: Carrier Inversion Induced by Helical Homochirality, J.Am. Chem. Soc. 134, 19600-19603 (2012).