Matthew Lauer - Synthesis, Spectroscopy, and Theoretical Calculations for a Series of Push−Pull [14]-Pyridoannulenes

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      Publication Details (including relevant citation   information):

      J. Org. Chem. 2008,73,474-484.


      Three new isomeric dipyridoannulenes were synthesized and   characterized. These molecules possess differing conjugation   pathways between the substituent alkoxy donating groups and the   pyridyl acceptor groups. Optical absorption and emission   properties of the dipyridoannulenes and their corresponding   acyclic precursors were measured and correlated to structural   differences and used to evaluate conjugation effectiveness and   charge-transfer pathways. Optical properties of protonated   dipyridoannulenes were also measured and found to be somewhat   insensitive to the degree of protonation. Density functional   studies of these systems at the B3LYP/6-31G* level provided   insight into their stabilities, polarities, and quinoidal   character. An analysis of the **** and LUMO molecular orbitals   provided further information regarding charge-transfer behavior.   These systems are good metal binding candidates, as the pyridine   moiety can act as both an electron-acceptor and a site for metal   coordination.

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