CN104817564B - 一种罗丹明‑(4‑二甲基氨乙基氨基‑1,8‑萘二甲酰亚胺)荧光分子及其制备方法和应用 - Google Patents
一种罗丹明‑(4‑二甲基氨乙基氨基‑1,8‑萘二甲酰亚胺)荧光分子及其制备方法和应用 Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 14
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 10
- 210000004881 tumor cell Anatomy 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- SSMIFVHARFVINF-UHFFFAOYSA-N 4-amino-1,8-naphthalimide Chemical compound O=C1NC(=O)C2=CC=CC3=C2C1=CC=C3N SSMIFVHARFVINF-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 3
- 238000005915 ammonolysis reaction Methods 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000004020 luminiscence type Methods 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims 1
- 239000012216 imaging agent Substances 0.000 claims 1
- 210000004027 cell Anatomy 0.000 abstract description 9
- 238000003384 imaging method Methods 0.000 abstract description 6
- 230000002776 aggregation Effects 0.000 abstract description 5
- 238000004220 aggregation Methods 0.000 abstract description 5
- 238000000799 fluorescence microscopy Methods 0.000 abstract description 2
- 239000000523 sample Substances 0.000 abstract description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 229960004756 ethanol Drugs 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- -1 Hg2+ Ions Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 4
- 238000002866 fluorescence resonance energy transfer Methods 0.000 description 4
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
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- 230000003287 optical effect Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910001430 chromium ion Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
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- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 230000012447 hatching Effects 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 229910052752 metalloid Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005415 bioluminescence Methods 0.000 description 1
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- 239000013043 chemical agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001215 fluorescent labelling Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
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- 238000002372 labelling Methods 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- BYVCTYDTPSKPRM-UHFFFAOYSA-N naphthalene-1-carbonyl naphthalene-1-carboxylate Chemical class C1=CC=C2C(C(OC(=O)C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 BYVCTYDTPSKPRM-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Abstract
本发明公开了一种罗丹明‑(4‑二甲基氨乙基氨基‑1,8‑萘二甲酰亚胺)荧光分子，它是包含罗丹明及4‑二甲基氨乙基氨基‑1,8‑萘二甲酰亚胺两种荧光团，通过2个亚甲基相连得到的一种新型荧光分子。本发明还公开了该荧光分子的制备方法和应用。本发明的罗丹明‑(4‑二甲基氨乙基氨基‑1,8‑萘二甲酰亚胺)荧光性能优异，可作为灵敏的Hg2+金属离子荧光探针,并且具有聚集诱导发光性质，可作为有机荧光染料用于肿瘤细胞荧光成像，在活细胞成像、荧光传感器、生物荧光标记等领域具有极其重要的应用价值。
Description
技术领域
本发明涉及一种荧光分子及其制备方法和应用，具体涉及一种罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子及其制备方法和应用。
背景技术
罗丹明-萘二甲酰亚胺双基团荧光分子灵敏度高，选择性强，结构易调控，其识别行为所表达的信息可用于复杂生物和环境体系的研究，在细胞成像、荧光传感器、生物荧光标记等领域具有极为重要应用前景。2008年，Zhou等报道了荧光共振能量转移的罗丹明-萘二甲酰亚胺铬离子荧光探针(Zhiguo Zhou,Mengxiao Yu,Hong Yang,Kewei Huang,FuyouLi,Tao Yi and Chunhui Huang.FRET-based sensor for imaging chromium(III)inliving cells.Chemical Communication,2008,3387–3389)；2011年，Kumar等报道了跨键能量转移的罗丹明-萘二甲酰亚胺汞离子探针(Manoj Kumar,Naresh Kumar,VandanaBhalla,Hardev Singh,Parduman Raj Sharma,and Tandeep Kaur.NaphthalimideAppended Rhodamine Derivative:Through Bond Energy Transfer for Sensing of Hg2+Ions.Organic Letters,2011,13(6),1422-1425)；2014年，Hu等报道了基于荧光共振能量转移-光诱导电子转移机制的罗丹明-4-羟乙基哌嗪萘二甲酰亚胺铬离子荧光探针(Fangzhi Hu,Baozhan Zheng,Dongmei Wang,Maoping Liu,Juan Du and Dan Xiao.Anovel dual-switch fluorescent probe for Cr(III)ion based on PET–FRETprocesses.Analyst,2014,139,3607–3613).设计开发高效灵敏的新型罗丹明-1,8-萘二甲酰亚胺类荧光探针是近年来的研究热点。
发明内容
本发明的第一个目的是提供一种罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子。本发明的第二个目的是提供上述罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子的制备方法。本发明的第三个目的是提供上述罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子的应用。
本发明采用以下技术方案：
一种罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子，由如下结构式构成：
上述罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子的制备方法，包括如下步骤：在无水乙醇中及氮气保护下由罗丹明-乙基胺与4-溴-1,8-萘二甲酸酐进行酸酐氨解反应,再与N,N-二甲基-1,2-乙二胺进行芳香亲核取代反应，制得所述荧光分子。
上述罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子在作为金属离子Hg2+荧光探针方面的应用。
上述罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子在肿瘤细胞成像方面的应用。
上述罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子在作为聚集诱导发光材料方面的应用。
本发明的有益效果：本发明将罗丹明荧光团和4-(N,N-二甲基氨基乙基)氨基-1,8-萘二甲酰亚胺荧光团通过2个亚甲基间隔基相连，得到一种新型多重识别的罗丹明-萘二甲酰亚胺荧光分子，该荧光分子在现有技术中未见报道。本发明荧光分子信息表达通过间隔基传递识别基结合客体分子所产生的作用信息，灵敏调控荧光性能。本发明的荧光分子性能优异，罗丹明中螺环隐色体闭环-开环结构互变、4-(N,N-二甲基氨基乙基)氨基-1,8-萘二甲酰亚胺中光诱导电子转移以及罗丹明与萘二甲酰亚胺2种荧光团之间的荧光共振能量转移多重识别机制并存，同时还具有很强的聚集诱导发光性能，溶解性好，稳定性高，选择性强，可作为灵敏的金属离子Hg2+荧光探针，以及作为荧光染料用于肿瘤细胞荧光成像，在活细胞成像、荧光传感器、生物荧光标记等领域具有极其重要的应用价值。
附图说明
图1是罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN与Hela细胞共同孵化后的激光共聚焦荧光照片。
图2是罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN在水/乙醇溶液中(水与乙醇的体积比7：3，Rh-NAEN荧光分子的浓度为10-5mol/L)分别加入不同种类金属离子(Li+,Ag+,Ca2+,Cd2+,Co2+,Cu2+,Fe2+,Mn2+,Ni2+,Sn2+,Zn2+,Zr2+,Fe3+,Al3+,Cr3+,Sn4 +and Hg2+,金属离子浓度均为2×10-5mol/L)的荧光光谱。
图3是罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN在水/乙醇溶液中(水与乙醇的体积比7：3，Rh-NAEN荧光分子的浓度为10-5mol/L)分别加入不同种类金属离子(Li+,Ag+,Ca2+,Cd2+,Co2+,Cu2+,Fe2+,Mn2+,Ni2+,Sn2+,Zn2+,Zr2+,Fe3+,Al3+,Cr3+,Sn4 +and Hg2+,金属离子浓度均为2.0×10-5mol/L)的荧光照片。
图4为罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN(Rh-NAEN的浓度为10-6mol/L)与含有Hg2+离子(Hg2+离子的浓度为10-6mol/L)Hela细胞共同孵化后的红光通道荧光照片。
图5为不同含水量时罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN在最大发射波长处荧光强度变化趋势图。
具体实施方式
下面结合实施例和附图对本发明做更进一步地解释。下列实施例仅用于说明本发明，但并不用来限定本发明的实施范围。
实施例1罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN的制备
4-溴-1,8-萘二甲酸酐从西亚试剂有限公司购买；N,N-二甲基-1,2-乙二胺从上海晶纯生化科技股份有限公司购买；罗丹明B从天津市化学试剂研究所购买。纯度均为分析纯。
化合物罗丹明-乙基胺(Rh-NH2)按文献方法制备(Xuan Zhang,YasuhiroShiraishi,Takayuki Hirai.Cu(II)-selective green fluorescence of a rhodamine-diacetic acid conjugate.Organic Letters,2007,9(24),5039-5042)：氮气保护下罗丹明B与乙二胺在无水乙醇中回流反应得到化合物Rh-NH2。
罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子的合成路线如下：
将2.66g(5.49mmol)化合物罗丹明-乙基胺(Rh-NH2)溶于80mL无水乙醇中，加入1.38g(4.98mmol)的4-溴-1,8-萘二甲酸酐，磁力搅拌，氮气保护下回流反应12h，反应结束后，蒸馏浓缩反应液，用柱色谱及重结晶提纯，得到橙色晶体Rh-NABr，产率86％。
分析所得化合物Rh-NABr：
1H NMR(300MHz,CDCl3,ppm):δ8.44(dd,J1＝7.53Hz,J2＝8.73Hz,2H),8.22(d,J＝7.83Hz,1H),δ7.84～7.90(m,2H),7.71(t,J1＝7.80Hz,J2＝7.95Hz,1H),7.30～7.37(m,2H),6.91～6.93(m,1H),6.34(d,J＝8.76Hz,2H),6.19(s,2H),5.80(d,J＝7.38Hz,2H),4.24(t,J1＝J2＝5.19Hz,2H),3.43(t,J1＝5.43Hz,J2＝5.40Hz,2H),3.00～3.08(m,8H),1.00(t,J1＝J2＝6.96Hz,12H).
获得的化合物结构式为
在25mL(0.28mol)N,N-二甲基-1,2-乙二胺中加入0.20g(0.27mmol)Rh-NABr以及0.02g(0.50mmol)NaOH，磁力搅拌，氮气保护下，100℃回流反应16h。反应结束后，冷却至室温，加入50mL水，过滤，干燥，用柱色谱及重结晶提纯，得到黄色固体Rh-NAEN，产率69％。
分析所得化合物Rh-NAEN：
1H NMR(300MHz,CDCl3,ppm):δ8.48(d,J＝7.20Hz,1H),8.35(d,J＝8.28Hz,1H),8.22(d,J＝8.22Hz,1H),7.90～7.93(m,1H),7.56(t,J1＝7.71Hz,J2＝7.98Hz,1H),7.39～7.44(m,2H),7.02～7.05(m,1H),6.61(d,J＝8.43Hz,1H),6.49(d,J＝8.85Hz,2H),6.35(s,2H),6.02(dd,J1＝2.31Hz,J2＝2.34Hz,2H),4.19(t,J1＝6.06Hz、J2＝6.09Hz,2H),3.52(t,J1＝6.00Hz、J2＝6.09Hz,2H),3.44～3.46(m,2H),3.16～3.23(m,8H),2.88(s,2H),2.46(s,6H),1.10(t,J1＝J2＝6.99Hz,12H).
13C NMR(CDCl3,ppm):δ168.07,163.44,153.31,152.88,148.67,147.97,133.54,131.58,130.95,130.29,128.35,127.25,124.02,123.27,122.37,110.28,107.43,105.32,103.64,97.36,64.70,56.46,44.36,43.68,39.54,38.73,38.26,29.18,12.15.
HRMS Calcd for C46H51N6O4[M+H]+751.3972 Found 751.3967.
获得的化合物结构式为
将实施例1制备的罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN进行实施例2～4的试验，具体数据和分析如下。
实施例2罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子用于肿瘤细胞成像
在1mL PBS缓冲液中将Hela细胞与10μL罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN(Rh-NAEN的浓度为10-6mol/L)共同孵化10min。移走Rh-NAEN荧光分子和PBS缓冲液，用PBS缓冲液洗涤，再加入1mL PBS缓冲液，用共聚焦荧光显微镜拍照。如图1所示，加入荧光分子罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)孵化后的Hela细胞在激光共聚焦荧光显微镜下可以清晰成像，激发波长为435nm。表明，罗丹明-(4-氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN可用于肿瘤细胞成像。
实施例3罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子对Hg2+离子的检测
图2是罗丹明-(4-氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN在水/乙醇溶液中(水与乙醇的体积比7：3，Rh-NAEN的浓度为10-5mol/L)加入不同种类金属离子(Li+,Ag+,Ca2 +,Cd2+,Co2+,Cu2+,Fe2+,Mn2+,Ni2+,Sn2+,Zn2+,Zr2+,Fe3+,Al3+,Cr3+,Sn4+and Hg2+,金属离子浓度均为2.0×10-5mol/L)的荧光光谱。分别加入相同浓度不同种类的金属离子Li+,Ag+,Ca2+,Cd2+,Co2+,Cu2+,Fe2+,Mn2+,Ni2+,Sn2+,Zn2+,Zr2+,Fe3+,Al3+,Cr3+,Sn4+时，罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN荧光淬灭，荧光处于“off”关闭状态；当加入相同浓度的Hg2+金属离子时，罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN荧光强度陡增，荧光处于“on”打开状态。图3是罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN在水/乙醇溶液中(水与乙醇的体积比7：3，Rh-NAEN的浓度为10-5mol/L)分别加入不同种类金属离子(Li+,Ag+,Ca2+,Cd2+,Co2+,Cu2+,Fe2+,Mn2+,Ni2+,Sn2+,Zn2+,Zr2+,Fe3+,Al3+,Cr3+,Sn4+and Hg2+,金属离子浓度均为2.0×10-5mol/L)的荧光照片。在荧光灯下暗室中只有在加入Hg2+金属离子时，Rh-NAEN呈现明亮的绿色荧光；而加入其它金属离子，Rh-NAEN均没有荧光。罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN对金属离子Hg2+的识别表现出良好的选择性且不受共存金属离子的干扰，可用于活细胞中Hg2+离子的检测。
图4为罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN(Rh-NAEN的浓度为10-6mol/L)与含有Hg2+离子(Hg2+离子的浓度为10-6mol/L)Hela细胞共同孵化后的红光通道荧光照片(激发波长为435nm)。Rh-NAEN含有罗丹明和4-(N,N-二甲基氨基乙基)氨基-1,8-萘二甲酰亚胺双荧光团，对金属离子Hg2+的识别存在多重识别机制，可实现多波长多通道识别和荧光调控，是灵敏的金属离子Hg2+荧光探针。
实施例4罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子的聚集诱导发光性质
暗室中荧光分子Rh-NAEN的固体粉末在紫外灯下发出明亮的黄绿色荧光。在溶液中Rh-NAEN的荧光随含水量的不同而变化，图5为不同含水量时罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN在最大发射波长处荧光强度变化趋势图。在Rh-NAEN的乙醇溶液中逐渐增加含水量，含水量为70％(体积百分比)以下，随着含水量的增加，Rh-NAEN荧光减弱，含水量为70％时荧光最弱；当含水量超过70％(体积百分比)时，Rh-NAEN荧光强度陡增。表明，罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子Rh-NAEN具有聚集诱导发光特性，可作为聚集诱导发光材料，具有极其重要的应用价值。
Claims (5)
1.一种罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子，其特征在于，由如下结构式构成：
2.权利要求1所述的罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子的制备方法，其特征在于，包括如下步骤：在无水乙醇中及氮气保护下由罗丹明-乙基胺与4-溴-1,8-萘二甲酸酐进行酸酐氨解反应,再与N,N-二甲基-1,2-乙二胺进行芳香亲核取代反应，制得所述荧光分子。
3.权利要求1所述的罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子在作为金属离子Hg2+荧光探针方面的应用。
4.权利要求1所述的罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子在制备肿瘤细胞成像试剂方面的应用。
5.权利要求1所述的罗丹明-(4-二甲基氨乙基氨基-1,8-萘二甲酰亚胺)荧光分子在作为聚集诱导发光材料方面的应用。
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