Protonation behaviour of 2-phenyl-1,3-diazaazulene derivatives

Add time:07/30/2019    Source:sciencedirect.com

Three 2-phenyl-1,3-diazaazulene derivatives were synthesized and their protonation behaviours were investigated systematically via UV–vis absorption titration and 1H NMR titration, as well as theoretical calculations. One of them exhibited a monoprotonation process while the others displayed prominent halochromic diprotonation responses. Interestingly, upon protonation of 2-phenyl-1,3-diazaazulene derivatives, the coplanarity and conjugation of the 16-π-conjugated backbones were well kept, while the electronic structures were controllably adjusted. The response mechanism of 1,3-diazaazulene derivatives towards acid is through the attachment of acid proton to the nitrogen atom in the diazaazulene ring, resulting in the change of the hybridization of protonated-N from sp2 to sp3, which differed from that of the well-known azulene (analogue of 1,3-diazaazulene, protonation at carbon atom). This work would provide a new insight into the protonation research of the organic functional molecules.

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