新型萘酰亚胺衍生物的制备及其对曙红的荧光增强作用研究
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摘要
以三聚氯氰、脂肪族二胺、1,8-萘酰亚胺和2-萘酚等为主要原料,合成了一系列新型萘酰亚胺衍生物荧光分子。考察了各种产物的热稳定性以及紫外-可见吸收和荧光发射性能。进一步用其与曙红组成能量转移体系,研究了产物对曙红的荧光增强作用。具体包括以下内容:
1、含有1个、2个、3个萘酰亚胺荧光团的化合物的合成与表征:控制反应条件,分别用4-氨基乙基氨基-N-正丁基-1,8-萘酰亚胺(EBNP)取代三聚氯氰(CNC)的1个、2个、3个氯原子,合成了含有1个、2个、3个萘酰亚胺荧光团的化合物CBNT、BCBNT、TCBNT。优化了各个产物的合成条件。通过元素分析,红外光谱,核磁共振,质谱等对产物的结构进行了表征。
2、含有1个萘酰亚胺荧光团和2个萘荧光团的化合物的合成与表征:分别用2份2-萘酚和1份4-氨基乙基氨基-N-正丁基-1,8-萘酰亚胺(EBNP)取代1份三聚氯氰(CNC)的3个氯原子,合成了含有1个萘酰亚胺荧光团和2个萘荧光团的化合物NCBNT。优化了合成条件,通过元素分析,红外光谱,核磁共振,质谱等对产物的结构进行了表征。
3、含有4个萘酰亚胺荧光团的化合物的合成与表征:用三聚氯氰中2个氯原子被EBNP取代的产物(BCBNT)和乙二胺反应,合成了含有4个萘酰亚胺荧光团的化合物G1.0(EBNP)_4。通过元素分析,红外光谱,核磁共振,质谱等对其结构进行了表征。
4、荧光分子的热稳定性研究:考察了产物CBNT,BCBNT,TCBNT与NCBNT和G1.0(EBNP)_4的热稳定性。热失重分析表明各种产物都具有较好的热稳定性。
5、荧光分子的紫外-可见吸收和发射光谱研究:测定了产物的紫外-可见吸收光谱和荧光发射光谱。相同浓度下,产物在DMF中的紫外-可见吸收光谱强度由大到小的顺序依次为:G1.0(EBNP)4＞TCBNT＞BCBNT＞NCBNT＞CBNT。产物的DMF溶液的荧光强度都随浓度的增加先增强后减弱。CBNT,BCBNT,NCBNT在5×10~(-5)mol/L时荧光最强,TCNBT在2.0×10~(-5)mol/L时荧光最强,G1.0(EBNP)在2.5×10~(-5)mol/L时荧光最强。在2.0×10~(-5)mol/L时荧光强度由大到小的顺序依次为:TCBNT＞BCBNT＞G1.0(EBNP)4＞NCBNT＞CBNT。
6、产物对曙红的荧光增强作用研究:将CBNT,NCBNT,BCBNT,TCBNT,G1.0(EBNP)4分别与曙红构成能量转移体系,发现在一定的浓度范围内,这些分子均可以将自身吸收的能量部分转移给曙红,使曙红的特征发射强度增强。CBNT,NCBNT,BCBNT,TCBNT,G1.0(EBNP)4对曙红的荧光强度增强的最大倍数依次为6.6,9.4,14.6,12.0,5.9。增强作用由大到小的顺序为:BCBNT＞TCBNT＞NCBNT＞CBNT＞G 1.0(EBNP)4。
A series of novel fluorescent naphthalimide derivatives were synthesized with 2,4,6-trichloro-1,3,5-triazine(CNC),aliphatic diamine,1,8-naphthalimide andβ-naphthol as primary raw materials.Thermostability,UV/Vis absorption and fluorescent performances of the obtained products had been investigated.Furthermore,the synthesized compounds were used for constructing energy transfer systems with eosin and their fluorescence enhancement to eosin was studied.The contents were as follows:
1、Synthesis and characterization of compounds with one,two and three 1,8-naphthalimide fluorophores:Through controlling reaction conditions,one,two or three chlorine atoms in 2,4,6-trichloro-1,3,5-triazine(CNC) were substituted by 4-amino-ethylamino-N-n-butyl-1,8-naphthalimide(EBNP) to get compounds with one, two and three 1,8-naphthalimide fluorophores CBNT,BCBNT and TCBNT.The reaction conditions were optimized,and the structures of the products were characterized by elementary analysis,FTIR,~1H-NMR and MS.
2、Synthesis and characterization of compound with one 1,8- naphthalimide fluorophore and two naphthalene fluorophores:Three chlorine atoms in one equivalent 2,4,6-trichloro-1,3,5-triazine(CNC) were substituted by two equivalent 2-naphthol and one equivalent 4-amino-ethylamino-N-n-butyl-1,8-naphthalimide to achieve compound with one 1,8- naphthalimide fluorophore and two naphthalene fluorophores NCBNT.The reaction conditions were optimized,and the structure of the product was characterized by elementary analysis,FTIR,~1H-NMR and MS.
3、Synthesis and characterization of compound containing four 1,8-naphthalimide fluorophores:The compound containing four 1,8-naphthalimide fluorophores G1.0(EBNP)4 was synthesized by the reaction of BCBNT and 1,2-ethylenediamine.The structure of the product was characterized by elementary analysis,FTIR,~1H-NMR and MS.and MS.
4、Investigation of the thermostability of the fluorescent molecules:The thermostability of CBNT,BCBNT,TCBNT,NCBNT and G1.0(EBNP)_4 were investigated.TGA analysis of the products showed that all of them had good thermostability.
5、Study on UV/Vis absorption and emission spectra of the fluorescent molecules:The UV/Vis absorption and fluorescent emission spectra of CBNT,BCBNT, TCBNT,NCBNT and G1.0(EBNP)4 were tested.The order of the absorption abilities of their DMF solutions with the same concentration is G1.0(EBNP)4 >TCBNT > BCBNT > NCBNT > CBNT.The fluorescent intensity of products in DMF solution increased at first,then decreased when the concentration rose,and at the concentration of 5×10~(-5) mol/L,CBNT,BCBNT,NCBNT got their maximum fluorescent intensity,and at the concentration of 2.0×10~(-5) mol/L,TCBNT got the maximum fluorescent intensitywhile,and at the concentration of 2.5×10~(-5) mol/L,G1.0(EBNP)4 got the maximum fluorescent intensity,the rank of fluorescent intensity was TCBNT>BCBNT>G1.0(EBNP)4>NCBNT>CBNT at the concentration of 2.0×10~(-5) mol/L.
6,Study on the fluorescence enhaneement to eosin by the products:The energy transfer systems of CBNT/eosin,NCBNT/eosin,BCBNT/eosin,TCBNT/eosin, G1.0(EBNP)4/eosin were studied.It was found that all the synthesized molecules could partially transfer their absorption energy to eosin at a certain range of concentrations. The maximum fluorescent enhancement by CBNT,NCBNT,BCBNT,TCBNT, G1.0(EBNP)4 to eosin was 6.6,9.4,14.6,12.0,5.9 fold respectively.The rank of their fluorescence-enhancement abilities was BCBNT >TCBNT > NCBNT > CBNT > G1.0(EBNP)4.
1、含有1个、2个、3个萘酰亚胺荧光团的化合物的合成与表征:控制反应条件,分别用4-氨基乙基氨基-N-正丁基-1,8-萘酰亚胺(EBNP)取代三聚氯氰(CNC)的1个、2个、3个氯原子,合成了含有1个、2个、3个萘酰亚胺荧光团的化合物CBNT、BCBNT、TCBNT。优化了各个产物的合成条件。通过元素分析,红外光谱,核磁共振,质谱等对产物的结构进行了表征。
2、含有1个萘酰亚胺荧光团和2个萘荧光团的化合物的合成与表征:分别用2份2-萘酚和1份4-氨基乙基氨基-N-正丁基-1,8-萘酰亚胺(EBNP)取代1份三聚氯氰(CNC)的3个氯原子,合成了含有1个萘酰亚胺荧光团和2个萘荧光团的化合物NCBNT。优化了合成条件,通过元素分析,红外光谱,核磁共振,质谱等对产物的结构进行了表征。
3、含有4个萘酰亚胺荧光团的化合物的合成与表征:用三聚氯氰中2个氯原子被EBNP取代的产物(BCBNT)和乙二胺反应,合成了含有4个萘酰亚胺荧光团的化合物G1.0(EBNP)_4。通过元素分析,红外光谱,核磁共振,质谱等对其结构进行了表征。
4、荧光分子的热稳定性研究:考察了产物CBNT,BCBNT,TCBNT与NCBNT和G1.0(EBNP)_4的热稳定性。热失重分析表明各种产物都具有较好的热稳定性。
5、荧光分子的紫外-可见吸收和发射光谱研究:测定了产物的紫外-可见吸收光谱和荧光发射光谱。相同浓度下,产物在DMF中的紫外-可见吸收光谱强度由大到小的顺序依次为:G1.0(EBNP)4＞TCBNT＞BCBNT＞NCBNT＞CBNT。产物的DMF溶液的荧光强度都随浓度的增加先增强后减弱。CBNT,BCBNT,NCBNT在5×10~(-5)mol/L时荧光最强,TCNBT在2.0×10~(-5)mol/L时荧光最强,G1.0(EBNP)在2.5×10~(-5)mol/L时荧光最强。在2.0×10~(-5)mol/L时荧光强度由大到小的顺序依次为:TCBNT＞BCBNT＞G1.0(EBNP)4＞NCBNT＞CBNT。
6、产物对曙红的荧光增强作用研究:将CBNT,NCBNT,BCBNT,TCBNT,G1.0(EBNP)4分别与曙红构成能量转移体系,发现在一定的浓度范围内,这些分子均可以将自身吸收的能量部分转移给曙红,使曙红的特征发射强度增强。CBNT,NCBNT,BCBNT,TCBNT,G1.0(EBNP)4对曙红的荧光强度增强的最大倍数依次为6.6,9.4,14.6,12.0,5.9。增强作用由大到小的顺序为:BCBNT＞TCBNT＞NCBNT＞CBNT＞G 1.0(EBNP)4。
A series of novel fluorescent naphthalimide derivatives were synthesized with 2,4,6-trichloro-1,3,5-triazine(CNC),aliphatic diamine,1,8-naphthalimide andβ-naphthol as primary raw materials.Thermostability,UV/Vis absorption and fluorescent performances of the obtained products had been investigated.Furthermore,the synthesized compounds were used for constructing energy transfer systems with eosin and their fluorescence enhancement to eosin was studied.The contents were as follows:
1、Synthesis and characterization of compounds with one,two and three 1,8-naphthalimide fluorophores:Through controlling reaction conditions,one,two or three chlorine atoms in 2,4,6-trichloro-1,3,5-triazine(CNC) were substituted by 4-amino-ethylamino-N-n-butyl-1,8-naphthalimide(EBNP) to get compounds with one, two and three 1,8-naphthalimide fluorophores CBNT,BCBNT and TCBNT.The reaction conditions were optimized,and the structures of the products were characterized by elementary analysis,FTIR,~1H-NMR and MS.
2、Synthesis and characterization of compound with one 1,8- naphthalimide fluorophore and two naphthalene fluorophores:Three chlorine atoms in one equivalent 2,4,6-trichloro-1,3,5-triazine(CNC) were substituted by two equivalent 2-naphthol and one equivalent 4-amino-ethylamino-N-n-butyl-1,8-naphthalimide to achieve compound with one 1,8- naphthalimide fluorophore and two naphthalene fluorophores NCBNT.The reaction conditions were optimized,and the structure of the product was characterized by elementary analysis,FTIR,~1H-NMR and MS.
3、Synthesis and characterization of compound containing four 1,8-naphthalimide fluorophores:The compound containing four 1,8-naphthalimide fluorophores G1.0(EBNP)4 was synthesized by the reaction of BCBNT and 1,2-ethylenediamine.The structure of the product was characterized by elementary analysis,FTIR,~1H-NMR and MS.and MS.
4、Investigation of the thermostability of the fluorescent molecules:The thermostability of CBNT,BCBNT,TCBNT,NCBNT and G1.0(EBNP)_4 were investigated.TGA analysis of the products showed that all of them had good thermostability.
5、Study on UV/Vis absorption and emission spectra of the fluorescent molecules:The UV/Vis absorption and fluorescent emission spectra of CBNT,BCBNT, TCBNT,NCBNT and G1.0(EBNP)4 were tested.The order of the absorption abilities of their DMF solutions with the same concentration is G1.0(EBNP)4 >TCBNT > BCBNT > NCBNT > CBNT.The fluorescent intensity of products in DMF solution increased at first,then decreased when the concentration rose,and at the concentration of 5×10~(-5) mol/L,CBNT,BCBNT,NCBNT got their maximum fluorescent intensity,and at the concentration of 2.0×10~(-5) mol/L,TCBNT got the maximum fluorescent intensitywhile,and at the concentration of 2.5×10~(-5) mol/L,G1.0(EBNP)4 got the maximum fluorescent intensity,the rank of fluorescent intensity was TCBNT>BCBNT>G1.0(EBNP)4>NCBNT>CBNT at the concentration of 2.0×10~(-5) mol/L.
6,Study on the fluorescence enhaneement to eosin by the products:The energy transfer systems of CBNT/eosin,NCBNT/eosin,BCBNT/eosin,TCBNT/eosin, G1.0(EBNP)4/eosin were studied.It was found that all the synthesized molecules could partially transfer their absorption energy to eosin at a certain range of concentrations. The maximum fluorescent enhancement by CBNT,NCBNT,BCBNT,TCBNT, G1.0(EBNP)4 to eosin was 6.6,9.4,14.6,12.0,5.9 fold respectively.The rank of their fluorescence-enhancement abilities was BCBNT >TCBNT > NCBNT > CBNT > G1.0(EBNP)4.
引文
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