Probing Peripheral H-Bonding Functionalities in BN-Doped Polycyclic Aromatic Hydrocarbons

• DOI: 10.1021/acs.joc.9b03202
• Publication Date: 2020-02-06T17:55:10Z
• Authors: Jonathan Tasseroul; Maria Mercedes Lo...; Jacopo Dosso; François Simon; Simone Velari; Alessandro De Vita; Paolo Tecilla; Davide Bonifazi
• Keywords: Heteroatom; Polycyclic aromatic hydrocarbon; Acceptor; Carbon fibers; Zigzag

The replacement of carbon atoms at the zigzag periphery a benzo[fg]tetracenyl derivative with an NBN atomic triad allows formation heteroatom-doped polycyclic aromatic hydrocarbon (PAH) isosteres, which expose BN mimics amidic NH functions. Their ability to form H-bonded complexes has never been touched so far. Herein, we report first solution recognition studies peripherally NBN-doped PAHs DD·AA- and ADDA·DAAD-type suitable complementary H-bonding acceptor partners. determination Ka in showed that 1:1 association strength is around 27 ± 1 M–1 for DD·AA C6D6, whereas it rises 1820 130 ADDA·DAAD array CDCl3. Given interest BN-doped polyaromatic hydrocarbons supramolecular materials chemistry, expected these findings will open new possibilities design novel materials, where properties peripheral hydrogens could serve as anchors tailor organizational PAHs.