4-(9-蒽基)-6-辛氧基-1,3,5-三嗪-2-胺的合成及其在酸性介质中的光谱行为研究

摘要

The synthesis of aminotriazine derivative, 4-(anthracen-9-yl)-6-(octyloxy)-1, 3, 5triazin-2-amine(AOOTA) was reported in this paper. With 2,4-dichloro-6- (octyloxy)-1, 3,5triazine as starting material, AOOTA was obtained through Kumada coupling and amination reaction in total yield of 380％. Spectroscopic behaviors of AOOTA with HOAc and TFA in chloroform were investigated by UV-Vis absorption and fluorescence spectra. It is found that the dual hydrogen-bonded interaction between AOOTA and HOAc can not be observed at both ground state and excited state. However, the dual hydrogen-bonded complex from AOOTA with TFA can be formed at ground state, but dissociated at excited state due to the rotation of C-C bond (between anthryl group and triazine) and C-O bond (between octyloxy group and triazine).%以2,4-二氯-6-辛氧基-1,3,5-三嗪为原料,经Kumada偶联及胺化两步反应合成了三嗪胺衍生物:4-(9-蒽基)-6-辛氧基-1,3,5-三嗪-2-胺(AOOTA), 总产率为 38%.通过紫外-可见吸收光谱及荧光光谱研究了氯仿溶液中AOOTA在乙酸(HOAc) 及三氟乙酸 (TFA) 作用下的光谱行为.研究发现AOOTA与HOAc在基态及激发态下均不能发生双氢键作用,而AOOTA与TFA相互作用基态下形成双氢键复合物, 激发态下由于分子中蒽基及辛氧基与三嗪环间的C-C单键以及C-O单键的自由旋转,从而使得AOOTA与TFA分子间不能形成有效的氢键相互作用.