Synthesis and characterization of fluorescent poly(aromatic amide) dendrimers
Aulenta, F., Drew, M.G.B., Foster, A., Hayes, W., Rannard, S., Thornthwaite, D.W., Worrall, D.R. and Youngs, T.G.A. (2005) Synthesis and characterization of fluorescent poly(aromatic amide) dendrimers. Journal of Organic Chemistry, 70 (1). pp. 63-78. ISSN 0022-3263
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To link to this article DOI: 10.1021/jo048799a
The synthesis of a series of poly(aromatic amide) dendrimers up to the second generation is described herein. The AB, building block used throughout the synthesis of the dendrimers was the allyl ester of 3,5-diaminocinnamic acid, which has been synthesized from 3,5-dinitrobenzoic acid in good yield with use of a four-step procedure. Dendron synthesis was achieved via a convergent approach with use of a sequence of deprotection/coupling steps. Two commercially available alcohols, L-menthol and citronellol, were coupled to the AB(2) monomer by using an alkyl diacid spacer and two core units; 1,7-diaminoheptane and tris(2-aminoethyl)amine have been used to produce the final dendrimers. Characterization was carried out by NMR and IR spectroscopies, MALDI-TOF mass spectrometry, GPC, and DSC. The novel monomer and dendritic derivatives exhibited a strong fluorescence emission in the visible region (lambda approximate to 500 nm) of the spectrum and a weak emission in the near-infrared (lambda approximate to 850 nm) upon excitation in the near-UV region. The fluorescence emission characteristics were found to be solvent and dendrimer generation dependent.