Photolyses Of Derivatives Of Naphthyl And Anthryl Phosphates And Methylphosphonates

Upon UV irradiation in acetonitrile, tri-1-naphthyl phosphate and di-1-naphthyl methylphosphonate underwent intramolecular rearrangement and ipso-coupling to give 1,2'-binaphthalen-1'-ol and 1,1'-binaphthalene, respectively. In the photolyses of tris(4-methoxy-1-naphthyl) phosphate and bis(4-methoxy-1-naphthyl) methylphosphonate in methanol, 4,4'-dimethoxy-1,1'-binaphthalene, 1',4,4'-trimethoxy- 1,2'-binaphthalene, and 2,4,4'-trimethoxy-1,1'-binaphthalene were generated. Tri-9-anthryl phosphate and di-9-anthryl methylphosphonate underwent intramolecular (4+4) photocycloaddition between two anthryl groups. The fluorescence spectra of the naphthyl derivatives had two emission bands ascribed to an intramolecular excimer and a monomer, but the fluorescence spectra of the anthryl derivatives had only a monomer emission band. These photoluminescence behaviors are closely related to the reactivities of the compounds.