Ferrocene-Substituted Naphthalenediimide with Broad Absorption and Electron-Transport Properties in the Segregated-Stack Structure.

A new naphthalenediimide (NDI) molecule, where two ferrocene (Fc) units were directly attached to both imide nitrogens (Fc-NDI-Fc), was synthesized. The Fc units provide high crystallinity to Fc-NDI-Fc with good solubility to conventional organic solvents. The Fc units also work as electron-donating substituents, in contrast to the electron-deficient NDI unit, resulting in broad charge-transfer absorption of Fc-NDI-Fc from the UV region to 1500 nm in the solid state. The crystal structure analysis revealed that Fc-NDI-Fc formed a segregated-stack structure. The DFT calculation based on the crystal structure showed that the NDI π-orbitals extended over two axes. The extended π-network of the NDI units led to the electron-transport properties of Fc-NDI-Fc, which was confirmed using a flash-photolysis time-resolved microwave conductivity technique.