Synthesis and Photoluminescent Properties of 1,1‘-Binaphthyl-Based Chiral Phenylenevinylene Dendrimers

Complutense University of Madrid, Madrid, Madrid, Spain
The Journal of Organic Chemistry (Impact Factor: 4.72). 05/2003; 68(8):3178-83. DOI: 10.1021/jo026222s
Source: PubMed


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)(2n)G(n)-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.

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