Abstract
Quinoxalino[2,3-b']porphyrins are pi-expanded porphyrins, having a quinoxaline fused to a beta,beta'-pyrrolic position of the porphyrin. They are used as components in systems proposed as 'molecular wires'. Knowledge of their redox properties is of value in the design of electron- or hole-conduction systems. In particular, the location of the charge density in the radical anions of quinoxalinoporphyrins can be modulated by peripheral functionalization. New theoretical treatments of electrochemical potentials are developed that identify the site of reduction in both the anions and the dianions of 33 quinoxalinoporphyrins. These molecules include free-base and metallated macrocycles substituted on the quinoxaline with electron-withdrawing groups (NO2, Cl, Br) and/or electron-donating groups (NH2, OCH3). Spectroelectrochemistry, density-functional theory calculations, and substituent-parameter models are used to verify the analysis. Five distinct patterns are observed for the locations of the first and second reductions; some of these patterns involve delocalized charges. Nitroquinoxalinoporphyrins with the nitro groups at the 5- and 6-quinoxaline positions are found to have quite different properties owing to distortions caused b...Continue Reading
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