Photoinduced Processes of Supramolecular Nanoarrays Composed of Porphyrin and Benzo[ghi]perylenetriimide Units through Triple Hydrogen Bonds with One-Dimensional Columnar Phases

One-dimensional supramolecular columnar phases composed of porphyrins (electron donor: D) and benzo[ghi]perylenetriimides (electron acceptor: A) through triple hydrogen bonds have been successfully constructed to perform sequential light-harvesting and electron-transfer processes. A series of benzo[ghi]peryleneimide derivatives have been synthesized to examine the substituent effects such as imide and nitrile groups on the spectroscopic and electrochemical properties. Then, formation of the 1:1 supramolecular complex between zinc porphyrin and benzo[ghi]perylenetriimide derivatives through triple hydrogen bonds was confirmed by Job's plot of ¹H NMR titration. Next, the one-dimensional supramolecular nanoarrays were successfully prepared in a mixed solvent. X-ray diffraction (XRD) measurement suggested that these nanoarrays contained one-dimensional columnar phases composed of stacked donor and acceptor layers. Finally, femtosecond transient absorption and electron spin resonance (ESR) measurements clearly indicated that photoinduced electron transfer occurred via the singlet excited states in the supramolecular columns.