posted on 2003-03-18, 00:00authored byEnrique Díez-Barra, Joaquín C. García-Martínez, Riánsares del Rey, Julián Rodríguez-López, Francesco Giacalone, José L. Segura, Nazario Martín
New chiral, soluble binaphthyl derivatives that incorporate stilbenoid dendrons at the 6,6‘-positions
have been prepared. The synthesis of the new enantiopure dendrimers was performed in a
convergent manner by Horner−Wadsworth−Emmons (HWE) reaction of the appropriately functionalized 1,1‘-binaphthyl derivative (R)-1 and the appropriate dendrons (R)2nGn-CHO. Different
electroactive units were incorporated in the peripheral positions of the dendrons in order to tune
both the optical and electrochemical behavior of these systems. Fluorescence measurements on
the chiral dendrimers reveal a strong emission with maxima between 409 and 508 nm depending
upon the substitution pattern. Finally, the redox properties of the dendrimers were determined by
cyclic voltammetry, showing the influence of the functional groups at the peripheral positions of
the dendrimer on the redox behavior of these systems.