Synthesis and Photochemical Properties of Anthracene-Polyyne-Porphyrin Assemblies

Abstract A series of anthrylpolyynes (α-anthryl-ω-(formylphenyl)polyynes) and anthrylpolyynylporphyrins (5-[(anthrylpolyynyl)phenyl]porphyrins) have been synthesized, and their photochemical properties and photoinitiated intramolecular excitation energy transfer from anthracene to porphyrin were studied by picosecond time-resolved fluorescence spectroscopy. Although anthrylpolyynes have strong fluorescence emission and fluorescence high quantum yield, anthrylpolyynylporphyrins, in which porphyrin links to the other side of polyyne, show only typical fluorescence emission of porphyrin and almost no fluorescence emission in the spectral region of anthrylpolyynes. The excitation of anthryl substituent brings about an increase in the fluorescence emission of porphyrin on the picosecond time scale. The mechanism of quantitative energy transfer from the anthryl moiety to the porphyrin is discussed on the basis of the photochemical properties of the component molecules.