摘要
用三聚氯氰(CNC)和6-(2-氨基乙胺基)-2-丁基-苯并[de]异喹啉-1,3-二酮(EBNP)为原料,合成了一种具有强烈荧光的三聚氯氰衍生物:2-丁基-6-〔2-(4,6-二氯-1,3,5-三嗪基-2-氨基)乙胺基〕-苯并[de]异喹啉-1,3-二酮(CBNT)。优化的条件为:以无水四氢呋喃(THF)为溶剂,以N,N-2-异丙基乙胺(DIPEA)为碱,n(EBNP)∶n(CNC)∶n(DIPEA)=1∶1∶1,EBNP的四氢呋喃溶液的滴加速度为1 mL/min,反应温度0-5℃,反应时间4 h,目标产物产率可达97.5%。用元素分析、核磁共振、质谱、红外光谱对目标产物的结构进行了表征。考察了其紫外可见吸收和荧光发射光谱。与EBNP相比,目标产物的摩尔消光系数增大了1.01倍,最大荧光强度增强了66.8%。目标产物的荧光性能受溶剂影响。
A cyanuric chloride derivative with strong fluorescence :2-butyl-6 - [2-(4,6-dichloro-1,3,5- triazin-2-ylamino) -ethylamino] -benzo[de] isoquinoline-1,3-dione(CBNT) was prepared from eyanuric chloride ( CNC ) and 6- ( 2-amino-ethylamino ) -2-butyl-benzo [de ] isoquinoline-1,3 -dione (EBNP). The optimum reaction conditions included anhydrous tetrahydrofuran (THF) as solvent, N, N- diisopropylethylamine (DIPEA) as base, n (EBNP) :n ( CNC ) :n (DIPEA) = 1 : 1 : 1, the flow rate of THF solution of EBNP 1 mL/min, reaction temperature 0 - 5 ℃ and reaction time 4 h. The yield of the target product reached 97.5%. Structure of the target product was characterized by elementary analysis, MS, ^1HNMR and FTIR. Ultraviolet - visible absorption and fluorescence spectra of the target product were investigated. Compared with EBNP, the molar extinction coefficient of the target product was enhanced 1.01 folds, and its maximum fluorescent intensity increased by 66. 8%. The fluorescent performance of the target product was affected by solvent.
出处
《精细化工》
EI
CAS
CSCD
北大核心
2008年第11期1053-1057,共5页
Fine Chemicals
基金
国家自然科学基金(No.20574049)
江苏省教育厅自然科学基金(06KJB150103)
苏州大学在职获得博士学位人员科研资助经费(R2317224)
苏州大学第四批优秀青年骨干教师培养人选科研资助经费(R2317144)~~
关键词
三聚氯氰
1
8-萘酰亚胺
紫外可见吸收
荧光
功能材料
eyanuric chloride
1, 8-naphthalimide
ultraviolet-visible absorption
fluorescence
functional materials