水溶性萘酰亚胺树形分子的合成及其荧光探针性质  

Synthesis and Fluorescent Properties of Water-Soluble 1,8-Naphthalimide Dendron

作　　者：孙京府 钱鹰[1] 

机构地区：[1]东南大学化学化工学院,南京211189

出　　处：《有机化学》2015年第5期1104-1111,共8页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.61178057)资助项目~~

摘　　要：合成了2个水溶性萘酰亚胺树形分子叔丁氧基羰基-{N,N-双{4-{{5-(4-叔丁基苯基)-[1,3,4]-噁二唑}-2-苯基}-乙烯基-1,8-萘酰亚胺}-乙氨基羰乙基}乙二胺(DON)和4-哌啶基-9-乙氨基-{N,N-双{4-{{5-(4-叔丁基苯基)-[1,3,4]-噁二唑}-2-苯基}-乙烯基-1,8-萘酰亚胺}-乙氨基羰乙基}乙氨基-1,8-萘酰亚胺(DOPN).并通过核磁氢谱、核磁碳谱及高分辨质谱结构表征.测定了DON及DOPN的固体、纯THF及水溶液中的荧光光谱,实验发现暗室中紫外灯下固体DON和DOPN发出橘黄色荧光,最大发射波长分别为566和561 nm.在四氢呋喃(THF)溶液中发出蓝绿色荧光,最大吸收波长为360和395 nm,最大发射波长为489和492 nm,荧光量子产率为28.2%和20.4%.水溶液中最大吸收波长为367和408 nm,最大发射波长为563和552 nm.测定了DON和DOPN与Hela细胞共同孵化后在共聚焦荧光显微镜下的细胞成像.研究了DON对Sn2+的选择性识别实验,研究发现,Sn2+对DON有选择性荧光增强,Sn2+与DON配位数为2.萘酰亚胺树形分子DON和DOPN可溶于水,具有聚集诱导发光(AIE)性质,是一种优良的Sn2+荧光探针,可广泛应用于肿瘤定位、药学研究、荧光显微技术及纳米材料研究的应用等重要领域.Two novel compounds, water-soluble 1,8-naphthalimide dendrons tert-butoxycarbonyl-{N,N-bis{3,5-bis{2-（4- tert-butylphenyl）-5-[ 1,3,4]-oxadiazolyl } -styryl- 1,8-naphathlimide } -ethylaminocarbonylethyl } ethylamino} - 1,8-naphthalimide （DON） and 4-piperidyl-9-ethylamino-{N,N-bis{3,5-bis{2-（4-tert-butylphenyl）-5-[1,3,4]-oxadiazolyl}-styryl-1,8-naphathlimide}-ethylaminocarbonylethyl}ethylamino}- 1,8-naphthalimide （DOPN） were synthesized and characterized by ^1H NMR, ^13C NMR and HRMS techniques. Fluorescence spectra of DON and DOPN in solid, tetrahydrofuran and aqueous were measured. The results demonstrated that DON and DOPN performed orange fluorescence in the solid state and the maximum emission wavelength were 566 and 561 nm, respectively. Blue-green fluorescence was observed in tetrahydrofuran （THF） solution. The maximum absorption wavelengths were 399 and 395 nm, the maximum emission wavelengths were 489 and 492 nm, and the quantum yields were 28.2% and 20.4%, respectively. Besides, the maximum absorption wavelengths were 406 and 408 nm, and the maximum emission wavelength were 563 and 552 nm in aqueous. Two water-soluble 1,8-naphthalimide dendrons were applied for fluorescence imaging in Hela living cells. In addition, metal ion probe behavior of DON was detected. And DON exhibitted a selectivity for tin ion. With the incresing of concentration of tin ion, fluorescence intensity of DON was enhancing. The number of binding sites between tin ion and DON was 2. In a word, two water-soluble 1,8-naphthalimide dendrons, can be used as a flourescent probe for detection of tin, and can be further applied in living cell imaging.

关 键 词：萘酰亚胺树形分子 聚集诱导荧光 荧光探针 Sn2+探针 细胞成像 

分 类 号：O623.626[理学—有机化学]