Lee Jae Wook, Kim Hee Joo, Han Seung Choul, Kim Ji Hyeon, Jin Sung-Ho
Department of Chemistry, Dong-A University, Busan 604-714, Korea.
J Nanosci Nanotechnol. 2008 Sep;8(9):4635-9. doi: 10.1166/jnn.2008.ic59.
The synthetic strategy for the convergent synthesis of emissive poly(amido amine) (PAMAM) den-drimers having the core chromophore via the copper-catalyzed 1,3-dipolar cycloaddition reaction between alkyne and azide was described. 2,7-Diazido-9H-fluorene, designed and synthesized to serve as the core in dendrimer, was stitched with the propargyl-functionalized PAMAM dendrons by the click chemistry leading to the formation of fluorescent PAMAM dendrimers in high yields. The absorption and emission of the dendrimers were investigated. Their photophysical studies indicated that 2,7-diazido-9H-fluorene showed no fluorescence due to the quenching effect from the electron-rich alpha-nitrogen of the azido group but the dendrimers fluoresced due to the elimination of the quenching through the formation of the triazole ring.
描述了一种通过炔烃与叠氮化物之间的铜催化1,3-偶极环加成反应,用于收敛合成具有核心发色团的发光聚(酰胺胺)(PAMAM)树枝状大分子的合成策略。设计并合成了用作树枝状大分子核心的2,7-二叠氮基-9H-芴,通过点击化学将其与炔丙基官能化的PAMAM树枝状单元缝合,从而高产率地形成荧光PAMAM树枝状大分子。研究了树枝状大分子的吸收和发射。它们的光物理研究表明,由于叠氮基富电子α-氮的猝灭作用,2,7-二叠氮基-9H-芴不显示荧光,但树枝状大分子由于通过形成三唑环消除了猝灭而发出荧光。