Perylenecarboxydiimide-Gold(I) Organometallic Dyes. Optical Properties and Langmuir Films

Abstract

A new perylenediimide-isocyanide N,N’-bis(1-ethylpropyl)-1-isocyanide-perylene-3,4:9,10-bis(dicarboximide) (CN-PDI), as well as the isocyanide [AuY(CN-PDI)] and carbene [Au-Y-{C(NH-PDI) (NMe2)}] (Y = Cl, C6F5, 4-C6F4OC6H13, 1/2-μ-C6F4C6F4) gold complexes therefrom, have been synthesized and characterized. All complexes are strongly colored and display fluorescence in solution associated with the perylene fragment. The influence of the metal fragment on these properties is very small in the isocyanide complexes, but more pronounced in the carbene derivatives, revealing a higher electronic connection between the metal and the PDI group in the carbene-complexes. Stable Langmuir films are formed by CN-PDI, [C6F5-Au-CN-PDI] and [H13C6OC6F4-Au-CN-PDI], in which, remarkably, by varying the compression of the films at the air/water interface it is possible to modulate the molecular arrangement in LS multi-layered films.