摘要
通过3-甲酰基-7-N,N-二甲基氮杂香豆素(T1)与氨甲基吡啶的缩合反应,生成一个缩醛胺结构化合物NC-1而非席夫碱.通过对比产物分子NC-2~NC-4和结构优化计算研究了该反应的机理,确定了分子内氢键在反应中的稳定作用.光谱测试结果表明,NC-1能够分别与Zn2+,Cd2+和Cu2+作用,产生不同的荧光和吸收光谱变化,现象肉眼可见.
By condensation of 7-(dimethylamino)-2-oxo-2H-benzo[b][1,4]oxazine-3-carbaldehyde(T1) and 2-aminomethylpyridine, an aminal NC-1 rather than a Schiff base was synthesized. The synthetic mechanism was likely to be determined by stabilizing effect of intramolecular hydrogen bond, which was proved through density functional theory(DFT) calculations and control molecules NC-2~NC-4. Furthermore, the spectroscopic tests indicated that NC-1 behaves as a fluorescent probe for sensing Cd2+, Zn2+ and Cu2+ by different fluorescence and color changes which can be observed by naked eyes.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2014年第8期1623-1629,共7页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(No.21136002)
教育部新世纪优秀人才支持计划(No.NCET-12-0080)
辽宁省自然科学基金(No.2013020115)资助项目~~
关键词
氮杂香豆素
席夫碱
合成机理
荧光探针
aza-coumarin
Schiff base
synthesis mechanism
fluorescent probe
