New Perylene-Substituted Organotrialkynyltin Compounds for the Photosensitization of Tin Dioxide

Abstract

New perylene-substituted organotrialkynyltins C 10 H 20 Sp−Sn(C⋮CC 4 H 9 ) 3 ( 1; Sp = −C 4 H 8 −, −C 6 H 12 −, −CH CH−) have been synthesized in two steps from the tricyclohexyltin analogues in fair to high yields (30−90%). Tricyclohexyltin derivatives were prepared in 50% yields either by coupling of 3-perylenyllithium with a (ω-iodoalkyl)tricyclohexyltin or by hydrostannation of 3-ethynylperylene by tricyclohexyltin hydride. Intermolecular π−π contacts between the perylene units were found in the solid-state structure of 3-(4-(tricyclohexylstannyl)butyl)perylene. The presence of a (tricyclohexylstannyl)- or a (trialkynylstannyl)alkyl substituent does not affect the fluorescence emission properties of the perylene core, whereas an ω-(trichlorostannyl)alkyl or a 2-stannylethynyl group does. Molecules 1 are dye precursors for the photosensitization of nanocrystalline tin dioxide materials.