Non-planar nanographenes (NGs) are of high interest in the material sciences for their interesting optic, electronic, and other physical properties. Contortion in a NG structure can often render the compound chiral, and if the inversion barrier is high, these materials can become useful in applications such as chiral sensing, chiroptics, and switches. Chirality is often seen in NG structures in the form of helicity, which is due to van der Waals repulsion. We achieve this through a combination of consecutive ortho-fused benzene rings and substitution effects within the bay or cove region of a NG. Our key synthetic strategy is the use of consecutive intramolecular alkyne benzannulations to extend the pi-conjugation of smaller polycyclic aromatic hydrocarbons (PAHs) to arrive at much larger chiral NG structures. Some of these new structures and their interesting physical properties will be presented.

Synthesis of chiral nanographenes

ACS Spring Meeting 2021

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