UC San Diego

The understanding of a dye’s electronic nature is fundamentally important as well as vital to the rational design of subsequent dyes. The elucidation of the conjugation path in a naphthalene dye, substituted by a donor and acceptor on the long axis, is reported. This was accomplished via a combination of theoretical and empirical methods aimed at measuring the results of perturbing the electronic pi-structure. The replacement of methine units in naphthalene with nitrogen through the synthesis of analogues resulted in characteristic changes to the optical and electrochemical properties. These observations are consistent with the donor and acceptor being conjugated to specific positions in naphthalene. The results add to fundamental knowledge about the electronic nature of push-pull naphthalene, while directly providing a map of sites on naphthalene that may be synthetically targeted and altered to obtain bespoke dyes with desired photophysical or electrochemical properties.