Probing peripheral H-bonding functionalities in BN-doped polycyclic aromatic hydrocarbons

Jonathan Tasseroul, Maria Lorenzo-Garcia, Jacopo Dosso, Francois Simon, Simone Velari, Alessandro De Vita, Paolo Tecilla, Davide Bonifazi
J. Org. Chem., 2020, accepted.

Abstract

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

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