Kritchasorn Kantarod,a Thanapat Worakul,a Darunee Soorukram,a Chutima Kuhakarn,a Vichai Reutrakul,a Panida Surawatanawong,a Worawat Wattanathanab and Pawaret Leowanawat*a
aCenter of Excellence for Innovation in Chemistry (PERCH-CIC) and Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
bDepartment of Materials Engineering, Faculty of Engineering, Kasetsart University, Bangkok 10900, Thailand.
Distorted nanographenes, such as nonplanar, curved, and twisted polycyclic aromatic hydrocarbons (PAHs) have gained considerable attention due to their interesting optoelectronic, charge-transport, and self-assembly properties resulting from the intrinsic curvature. In this work, a novel strategy is developed for the synthesis of twisted PAHs containing dibenzopleiadiene moeity from 1,8-naphthalic anhydride derivatives and cyclic diaryliodonium salts through a palladium- catalyzed cascade [4 + 3] decarbonylative/decarboxylative annulation. The mechanism of the reaction is proposed and the molecular structure, photophysical properties, and frontier molecular orbitals of diverse dibenzopleiadiene-embeded polyaromatics are elucidated by X-ray crystallography, UV-Vis and fluorescence spectroscopy, and DFT calculations.
**This work was also selected as inner cover of Organic Chemistry Frontiers, 2021, volume 8, number 3.
Reference: Kantarod, K.; Worakul, T.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Surawatanawong, P.; Wattanathana, W.; Leowanawat, P., Dibenzopleiadiene-embeded polyaromatics via [4 + 3] annulative decarbonylation/decarboxylation. Org. Chem. Front. 2021, 8 (3), 522-530. (https://doi.org/10.1039/D0QO00942C)