Hydrolytic Stability of N-Methyl-2,6-dimesityl-4,4′-Pyrylogen Bis-tetrafluoroborate
journal contributionposted on 02.09.2011, 00:00 by Tamer T. El-Idreesy, Edward L. Clennan
Any type of content formally published in an academic journal, usually following a peer-review process.
The synthesis and characterization of a new mesityl ring-substituted pyrylogen with a substantially decreased rate of reaction with water is reported. Computational and experimental data are presented that suggest that addition of water to the pyrylium ring of this highly sterically shielded pyrylogen is reversible. On the other hand, experimental data suggest that the overall hydrolysis of this new sterically shielded pyrylogen, but not the parent pyrylogen, is irreversible. Two potential explanations for this behavior are presented and discussed. These results provide important new information that can be used to design and synthesize new electron transfer sensitizers that can be used even in highly aqueous environments.