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

doi:10.7517/j.issn.1674-0475.2011.01.24

影像科学与光化学 ›› 2011, Vol. 29 ›› Issue (1): 24-31.DOI: 10.7517/j.issn.1674-0475.2011.01.24

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

李春丽¹, 李宗耀¹, 徐莉², 韩辉¹, 王华^1,2

1. 河南大学特种功能材料教育部重点实验室, 河南开封 475004;
2. 河南大学化学化工学院, 河南开封 475004

收稿日期:2010-07-15 修回日期:2010-10-13 出版日期:2011-01-23 发布日期:2011-01-23
通讯作者: 王华,E-mail:hwang@henu.edu.cn.
基金资助:
国家自然科学基金资助项目(20972041,20672028);河南省杰出青年基金(104100510011);教育部新世纪优秀人才支持计划(NCET-05-0610)

Synthesis of 4-(anthracen-9-yl)-6-(octyloxy)-1,3,5-triazin-2-amine and its Spectroscopic Behavior in Acid Medium

LI Chun-li¹, LI Zong-yao¹, XU Li², HAN Hui¹, WANG Hua^1,2

1. Key Lab for Special Functional Materials of Ministry of Education, Henan University, Kaifeng 475004, Henan, P. R. China;
2. College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, Henan, P. R. China

Received:2010-07-15 Revised:2010-10-13 Online:2011-01-23 Published:2011-01-23

摘要/Abstract

摘要： 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.

关键词: 4-(9-蒽基)-6-辛氧基-1,3,5-三嗪-2-胺, 合成, 乙酸, 三氟乙酸, 吸收, 荧光

Abstract: The synthesis of aminotriazine derivative,4- (anthracen-9-yl)-6- (octyloxy)-1,3,5-triazin-2-amine (AOOTA) was reported in this paper.With 2,4-dichloro-6- (octyloxy)-1,3,5-triazine as starting material,AOOTA was obtained through Kumada coupling and amination reaction in total yield of 38%.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).

Key words: 4-(anthracen-9-yl)-6-(octyloxy)-1,3,5-triazin-2-amine, synthesis, acetic acid, trifluoroacetic acid, UV-Vis absorption, fluorescence

中图分类号:

李春丽, 李宗耀, 徐莉, 韩辉, 王华. 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[J]. 影像科学与光化学, 2011, 29(1): 24-31.

LI Chun-li, LI Zong-yao, XU Li, HAN Hui, WANG Hua. Synthesis of 4-(anthracen-9-yl)-6-(octyloxy)-1,3,5-triazin-2-amine and its Spectroscopic Behavior in Acid Medium[J]. Imaging Science and Photochemistry, 2011, 29(1): 24-31.

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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

Synthesis of 4-(anthracen-9-yl)-6-(octyloxy)-1,3,5-triazin-2-amine and its Spectroscopic Behavior in Acid Medium

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