Aulenta Francesca, Drew Michael G B, Foster Alison, Hayes Wayne, Rannard Steven, Thornthwaite David W, Worrall David R, Youngs Tristan G A
School of Chemistry, The University of Reading, Whiteknights, Reading RG6 6AD, UK.
J Org Chem. 2005 Jan 7;70(1):63-78. doi: 10.1021/jo048799a.
The synthesis of a series of poly(aromatic amide) dendrimers up to the second generation is described herein. The AB(2) 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 approximately 500 nm) of the spectrum and a weak emission in the near-infrared (lambda approximately 850 nm) upon excitation in the near-UV region. The fluorescence emission characteristics were found to be solvent and dendrimer generation dependent.
本文描述了一系列直至第二代的聚（芳族酰胺）树枝状大分子的合成。在树枝状大分子的整个合成过程中使用的AB(2)结构单元是3,5-二氨基肉桂酸的烯丙酯，它是由3,5-二硝基苯甲酸通过四步程序以良好的产率合成的。树枝状分子的合成是通过使用一系列脱保护/偶联步骤的收敛方法实现的。两种市售醇，L-薄荷醇和香茅醇，通过使用烷基二酸间隔基和两个核心单元与AB(2)单体偶联；1,7-二氨基庚烷和三（2-氨基乙基）胺已用于制备最终的树枝状大分子。通过NMR和IR光谱、MALDI-TOF质谱、GPC和DSC进行表征。新型单体和树枝状衍生物在光谱的可见光区域（λ约500nm）表现出强烈的荧光发射，而在近紫外区域激发时在近红外区域（λ约850nm）表现出微弱的发射。发现荧光发射特性取决于溶剂和树枝状分子的代数。
