Journal of Polymer Science Part A: Polymer Chemistry, Vol.46, No.2, 713-724, 2008
Syntheses, characterization, optical properties, and charge-transfer complexation study of fluorescent poly(aryl-ether-urea) dendrimers
An inexpensive and highly efficient synthesis of first example of fluorescent aromatic dendrimers having alternative ether and urea linkages without the need for protection and deprotection steps has been developed. Dendrons and dendrimers up to third generation, with amine end-groups, were prepared by convergent growth approach in high yield. A repetitive synthetic sequence of nucleophilic addition reaction between amine and regenerated isocyanate and reduction of nitro groups into amine are adopted for the synthesis of these dendrimers. The peripheries of the dendrimers contained 6, 12, and 24 amino groups, for the first, second, and third generation, respectively. Materials were characterized by FTIR, NMR, and MALDI-TOF MS spectrometry. These dendrimers were soluble in amide solvents, THF and acetone and displayed fluorescence maxima in the 440-500 nm range with relatively narrow peak widths indicating that they had pure and intense fluorescence. These dendrimers form charge-transfer (CT) complexes with electron acceptor molecules such as 7,7,8,8,-tetracyano-quino-dimethane and 1,1,2,2 tetracyanoethane as evidenced by UV-visible absorption spectra. (c) 2007 Wiley Periodicals, Inc.