Synthesis, structure, and optical properties of terminally sulfur-functionalized core-substituted naphthalene-bisimide dyes

The synthesis, characterization, and optical properties of a series of new 2,6-disubstituted naphthalene-bisimide dyes as molecular rods comprising terminal AcS groups is reported. The first series of dyes (1-3), comprising phenylhetero (Ph-X) core substituents, cover a broad range of the VIS spectrum, ranging from yellow (2) over red (3) to blue (1). The second series of dyes contains benzylhetero (Bn-X) core substituents (4-7). For the same heteroatom connecting the substituent to the naphthalene core, both series were found to display comparable colors. For the second series, the colors were blue (4), red (5), and violet (6, 7). The Ph-X-substituted dyes 1-3 are nonfluorescent, in contrast to the Bn-X-substituted compounds 4-7. This rich variety of optical features that can be adjusted by rather small alterations of the core substituents makes these structurally very comparable molecular rods ideal candidates for optically triggered molecular-transport investigations. Also, thanks to the terminal AcS groups, these compounds can be placed between nobel-metal electrodes for optically triggered transport experiments.