含均三嗪环的树枝块的合成及其对曙红和铕离子的荧光增强作用研究
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摘要
三氯均三嗪结构中的均三嗪环可以经受各种苛刻条件而不被破坏，三个氯原子可以通过控制温度分阶段与含活泼氢的官能团反应，而且对同一分子中的脂肪族伯氨基与羟基、脂肪族伯氨基与芳香族伯氨基、醇羟基和酚羟基有很好的选择性，从而可以省去官能团保护—解保护或钝化—活化步骤。本文利用这些特点设计合成了一系列新型结构的含均三嗪环的树枝块，并研究了其对曙红和铕离子的荧光增强作用。具体包括以下内容：
1．以对羟基偶氮苯(p-HAB)、β-萘酚为端基，三聚氯氰(CNC)、3，5-二羟基苄醇(DHA)为支化单体，1-羟基蒽醌(HYA)为核心，用收敛法合成了一系列新型结构的含均三嗪环的树枝块：第一代端基为偶氮苯的树枝块G1.0(DOT)、端基为萘氧基的树枝块G1.0(NOT)、端基为萘氧基、中心为蒽醌的树枝块G(NOE)、第二代端基为萘氧基的树枝块G2.0(NOT)。研究了反应物投料摩尔比，碱的种类和碱的用量，溶剂的种类，反应温度，反应时间等条件对目标产物收率的影响。
2．通过红外光谱，元素分析，核磁共振，质谱对树枝块的结构进行了分析表征。
3．考察了各个树枝块的热稳定性和溶解性。G1.0(DOT)、G1.0(NOT)、G(NOE)、G2.0(NOT)分别在300、260、350、290℃才开始大量分解，有较好的热稳定性。G1.0(DOT)溶于二氯甲烷，四氢呋喃，乙酸乙酯，丙酮，1，4-二氧六环，不溶于水、石油醚、无水乙醇；G1.0(NOT)溶于四氢呋喃、二氯甲烷、二氧六环、丙酮、乙酸乙酯，不溶于石油醚、无水乙醇和水；G(NOE)溶于四氢呋喃、二氯甲烷、二氧六环、丙酮、乙酸乙酯、无水乙醇，不溶于石油醚和水；G2.0(NOT)溶于四氢呋喃、二氯甲烷、二氧六环、丙酮、乙酸乙酯、无水乙醇和水，不溶于石油醚。
4．研究了各个树枝块与曙红，Eu~(3+)离子之间的能量转移情况。将G1.0(DOT)、G1.0(NOT)、G(NOE)、G2.0(NOT)分别与曙红或Eu~(3+)离子构成能量转移体系，发现在一定的浓度范围内，这些树枝块均可以将吸收的能量转移给曙红和Eu~(3+)离子，使曙红和Eu~(3+)离子的特征发射强度增强，曙红的荧光强度最大增强为原来的2.5倍；Eu~(3+)离子的荧光强度最大增强为原来的11.7倍。增强作用从大到小都为：G2.0(NOT)＞G(NOE)＞G1.0(NOT)＞G1.0(DOT)。溶剂对能量转移体系的荧光发射强度有很大影响。
1,3,5-Triazine in cyanuric chloride can bear harsh conditions, and the chlorine in cyanuric chloride is able to react with active hydrogen step by step by controlling temperature. It is selective to aliphatic primary amino group and hydroxyl, aliphatic and aromatic primary amino group, alcoholic hydroxyl and phenolic hydroxyl group that were in one molecule, so the protecting-deprotecting or inactivation-activation steps would not be necessary. In this paper a series of novel dendrons with 1,3,5-triazine structure were designed and synthesized. The synthesized compounds were investigated for fluorescent enhancement to eosin and Eu~(3+) ion. The contents were as follows:
1. A series of novel dendrons with 1,3,5-triazine structure were synthesized by convergent strategy using cyanuric chloride, p-hydroxyazobenzene,β-naphthol, 1-hydroxyanthraquinone, 3,5-dihydroxybenzyl. They were the first generation p-phenyl-azo-phenyloxy-terminated dendron G1.0(DOT), the first generation naphthyloxy-terminated dendron G1.0(NOT), the first generation naphthyloxy-terminated and 1-anthraquinonoxy-cored dendron G(NOE), and the second generation naphthyloxy-terminated dendron G2.0(NOT). The effects of the stuff molar ratio, the variety and dosage of base, the reaction temperature and time on the yields of the products were investigated.
2. The structure of the dendrons was characterized by elementary analysis, IR spectrum, ~1H-NMR and MS.
3. The thermo stability and solubility of dendrons were investigated. G1.0(DOT), G1.0(NOT), G(NOE) and G2.0(NOT) possess fairly thermo stability, since they started to decompose at 300, 260, 350 and 290℃respectively. G1.0(DOT) was soluble in dichloromethane, tetrahydrofuran, ethyl acetate, acetone, 1, 4-dioxane, not soluble in water, petroleum ether, absolute alcohol. G1.0(NOT) was soluble in tetrahydrofuran, dichloromethane, 1, 4-dioxane, acetone, ethyl acetate, not soluble in petroleum ether, absolute alcohol, water. G2.0(NOT) was soluble in tetrahydrofuran, dichloromethane, 1, 4-dioxane, acetone, ethyl acetate, absolute alcohol, water, not soluble in petroleum ether.
4. The energy transfer between dendrons and eosin or Eu~(3+) ion in solvent were investigated. When energy transfer systems were obtained from the interaction of G1.0(DOT), G1.0(NOT), G(NOE) and G2.0(NOT) with eosin or Eu~(3+) ion respectively, all the dendrons could partially transfer their absorbed energy to eosin and Eu~(3+) ion at a certain range of concentrations. The maximum fluorescent enhancement to eosin and Eu~(3+) ion was 2.5 and 11.7 fold respectively. Therank of the abilities of fluorescent enhancement of the dendrons was G2.0(NOT)＞G(NOE)＞G1.0(NOT)＞G1.0(DOT). Solvents contributed a great deal to fluorescent emission intensity of the energy transfer systems.
1．以对羟基偶氮苯(p-HAB)、β-萘酚为端基，三聚氯氰(CNC)、3，5-二羟基苄醇(DHA)为支化单体，1-羟基蒽醌(HYA)为核心，用收敛法合成了一系列新型结构的含均三嗪环的树枝块：第一代端基为偶氮苯的树枝块G1.0(DOT)、端基为萘氧基的树枝块G1.0(NOT)、端基为萘氧基、中心为蒽醌的树枝块G(NOE)、第二代端基为萘氧基的树枝块G2.0(NOT)。研究了反应物投料摩尔比，碱的种类和碱的用量，溶剂的种类，反应温度，反应时间等条件对目标产物收率的影响。
2．通过红外光谱，元素分析，核磁共振，质谱对树枝块的结构进行了分析表征。
3．考察了各个树枝块的热稳定性和溶解性。G1.0(DOT)、G1.0(NOT)、G(NOE)、G2.0(NOT)分别在300、260、350、290℃才开始大量分解，有较好的热稳定性。G1.0(DOT)溶于二氯甲烷，四氢呋喃，乙酸乙酯，丙酮，1，4-二氧六环，不溶于水、石油醚、无水乙醇；G1.0(NOT)溶于四氢呋喃、二氯甲烷、二氧六环、丙酮、乙酸乙酯，不溶于石油醚、无水乙醇和水；G(NOE)溶于四氢呋喃、二氯甲烷、二氧六环、丙酮、乙酸乙酯、无水乙醇，不溶于石油醚和水；G2.0(NOT)溶于四氢呋喃、二氯甲烷、二氧六环、丙酮、乙酸乙酯、无水乙醇和水，不溶于石油醚。
4．研究了各个树枝块与曙红，Eu~(3+)离子之间的能量转移情况。将G1.0(DOT)、G1.0(NOT)、G(NOE)、G2.0(NOT)分别与曙红或Eu~(3+)离子构成能量转移体系，发现在一定的浓度范围内，这些树枝块均可以将吸收的能量转移给曙红和Eu~(3+)离子，使曙红和Eu~(3+)离子的特征发射强度增强，曙红的荧光强度最大增强为原来的2.5倍；Eu~(3+)离子的荧光强度最大增强为原来的11.7倍。增强作用从大到小都为：G2.0(NOT)＞G(NOE)＞G1.0(NOT)＞G1.0(DOT)。溶剂对能量转移体系的荧光发射强度有很大影响。
1,3,5-Triazine in cyanuric chloride can bear harsh conditions, and the chlorine in cyanuric chloride is able to react with active hydrogen step by step by controlling temperature. It is selective to aliphatic primary amino group and hydroxyl, aliphatic and aromatic primary amino group, alcoholic hydroxyl and phenolic hydroxyl group that were in one molecule, so the protecting-deprotecting or inactivation-activation steps would not be necessary. In this paper a series of novel dendrons with 1,3,5-triazine structure were designed and synthesized. The synthesized compounds were investigated for fluorescent enhancement to eosin and Eu~(3+) ion. The contents were as follows:
1. A series of novel dendrons with 1,3,5-triazine structure were synthesized by convergent strategy using cyanuric chloride, p-hydroxyazobenzene,β-naphthol, 1-hydroxyanthraquinone, 3,5-dihydroxybenzyl. They were the first generation p-phenyl-azo-phenyloxy-terminated dendron G1.0(DOT), the first generation naphthyloxy-terminated dendron G1.0(NOT), the first generation naphthyloxy-terminated and 1-anthraquinonoxy-cored dendron G(NOE), and the second generation naphthyloxy-terminated dendron G2.0(NOT). The effects of the stuff molar ratio, the variety and dosage of base, the reaction temperature and time on the yields of the products were investigated.
2. The structure of the dendrons was characterized by elementary analysis, IR spectrum, ~1H-NMR and MS.
3. The thermo stability and solubility of dendrons were investigated. G1.0(DOT), G1.0(NOT), G(NOE) and G2.0(NOT) possess fairly thermo stability, since they started to decompose at 300, 260, 350 and 290℃respectively. G1.0(DOT) was soluble in dichloromethane, tetrahydrofuran, ethyl acetate, acetone, 1, 4-dioxane, not soluble in water, petroleum ether, absolute alcohol. G1.0(NOT) was soluble in tetrahydrofuran, dichloromethane, 1, 4-dioxane, acetone, ethyl acetate, not soluble in petroleum ether, absolute alcohol, water. G2.0(NOT) was soluble in tetrahydrofuran, dichloromethane, 1, 4-dioxane, acetone, ethyl acetate, absolute alcohol, water, not soluble in petroleum ether.
4. The energy transfer between dendrons and eosin or Eu~(3+) ion in solvent were investigated. When energy transfer systems were obtained from the interaction of G1.0(DOT), G1.0(NOT), G(NOE) and G2.0(NOT) with eosin or Eu~(3+) ion respectively, all the dendrons could partially transfer their absorbed energy to eosin and Eu~(3+) ion at a certain range of concentrations. The maximum fluorescent enhancement to eosin and Eu~(3+) ion was 2.5 and 11.7 fold respectively. Therank of the abilities of fluorescent enhancement of the dendrons was G2.0(NOT)＞G(NOE)＞G1.0(NOT)＞G1.0(DOT). Solvents contributed a great deal to fluorescent emission intensity of the energy transfer systems.
引文
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