新型咔唑类Schiff碱的合成与性能研究
摘要
Schiff碱是一类含有亚胺或甲亚胺(-C=N-)特征基团的有机化合物。由于其具有较强的配位能力、多样的配位形式、广泛的生物活性和良好的光学性质等特点,在医药、催化和功能材料等方面得到了广泛应用,从而引起了国内外科技工作者的研究兴趣。本文设计并合成了15个新型含咔唑基Schiff碱,通过核磁氢谱、质谱、元素分析及红外光谱等分析方法对其进行了结构表征。其研究工作主要包括:
(1)以咔唑和天然氨基酸为原料,合成了手性氨基醇和3-乙酰基-N-乙基咔唑两类中间体,并通过无溶剂法缩合,合成了6种新的含咔唑基手性氨基醇Schiff碱。对3-甲酰基-N-乙基咔唑中间体的合成条件进行了探索,发现N-乙基咔唑与POCl3和DMF的摩尔比为1:10:10时,单甲酰化的产率最高。
首次通过无溶剂法合成出了新型手性氨基醇类Schiff碱,研究了THF、无水乙醇、冰醋酸和无水乙醇-冰醋酸等溶剂体系以及无溶剂体系对目标手性氨基醇Schiff碱产率的影响。通过实验探究,发现采用溶剂体系时,反应条件温和,但目标手性氨基醇Schiff碱难于提纯;采用无溶剂法合成目标手性氨基醇Schiff碱,缩短了反应时间,无需添加催化剂,用混合溶剂重结晶便能使产物与杂质分离,纯度和产率颇高。当反应时间为40min、反应温度为95℃时大部分目手性氨基醇标Schiff碱的合成产率可达87%以上。
研究了氨基醇的结构对目标手性氨基醇Schiff碱的紫外光谱和发光性能的影响。发现氨基醇的结构对目标手性氨基醇Schiff碱的荧光光谱有明显的影响。通过荧光光谱分析发现Schiff碱L1的发光性能最好,其主要原因为苯丙氨醇存在芳环,使其分子结构具有良好的共轭性,增强了它的能量传递效率,导致其荧光强度增加。
(2)以咔唑、2-萘酚、水杨酸甲酯、对硝基苯甲酸、苯甲酸乙酯为原料,合成出了9个新的含咔唑基双酰腙类Schiff碱。探究了N-烷基咔唑的Friedel—Crafts酰基化反应和目标双酰腙类Schiff碱的合成条件,发现当N-烷基咔唑、乙酰氯和催化剂的摩尔比为1:5:4时,3,6-二乙酰基-N-烷基咔唑中间体的产率最高;当无水乙醇与冰醋酸的体积比为10:2时,目标双酰腙类Schiff碱的产率最高。研究了目标酰腙类Schiff碱的光谱性能,发现Schiff碱L7和L8具有较好的荧光性能。
Schiff base is a class of organic compounds which contain characteristic imine or azomethine group (-C=N-). The Schiff base aroused the interest of scholars both home and abroad, because of its various coordination forms, strong coordination ability, good biological activities and optical properties. Some of them have been widely applied in medicine, catalysis and photoelectric materials. In this paper, fifteen novel carbazol-containing Schiff bases were synthesized, and also characterized by 1H NMR, MS, IR, and elemental analyses. The works mainly include:
(1) The chiral amino alcohols and 3-formacyl-N-ethyl carbazole as the key intermediates were synthesized with the carbazole and natural amino-acid as the materials, and the synthesis conditions of 3-formacyl-N-ethyl carbazole were optimizated. The results show that the best yield of sing-formylation was obtained, when the volume ratio of N-ethyl carbazole, POCl3 and DMF is 1:10:10.
Six novel chiral amino alcohol Schiff bases were synthesized by the solvent-free reaction for the first time. The influence of the different organic solvent system (THF, EtOH, AcH, EtOH-AcH) and solvent-free system on the yields of the target chiral amino alcohol Schiff bases was studied in detail. The experimental results show that the synthesis conditions of the target chiral amino alcohol Schiff bases are mild in the organic solvent system, but the products are purified very difficultly. Compared with the previous method, the solvent-free method possess such advantages as short reaction time, without adding catalyst, high yield and only simple recrystallization purification in mixed solvent. The yield of the target chiral amino alcohol Schiff base was up to 87%, when the reaction temperature was at 95℃and the reaction time was 40 min.
The effect of the structure of the chiral amino alcohol on the spectral propertie of the target chiral amino alcohol Schiff bases was studied. The results indicat that the structure of the chiral amino alcohol have significant influence on their fluorescence, and the Schiff base L1 has the best fluorescence intensity. Because L-phenylglycinol possesses the aromatic rings, the conjugation effect of the molecular structure of the Schiff base L1 are improved, and its energy transfer efficiency is enhanced, its fluorescence intensity is increased.
(2) Nine novel carbazol-containing diacylhydrazone Schiff bases were synthesized with the carbazole, 2-naphthol, methyl salicylate, p-nitrobenzoic acid, and ethyl benzoate as the raw materials. And explored were the synthesis conditions of Friedel-Crafts acylation of N-alkyl carbazole and carbazol-containing diacylhydrazone Schiff bases. The experimental results show that the best yield of di-acetylation is obtained when the volume ratio of 9-alkyl carbazole, acetyl chloride, and catalyst is 1:5:4; the best yields of the target diacylhydrazone Schiff base is obtained when the volume ratio of ethanol and glacial acetic acid is 10:2. The spectral propertie of the target diacylhydrazone Schiff bases was studied, and the results indicat that Schiff base L7 and L8 have the best fluorescence intensity.
(1)以咔唑和天然氨基酸为原料,合成了手性氨基醇和3-乙酰基-N-乙基咔唑两类中间体,并通过无溶剂法缩合,合成了6种新的含咔唑基手性氨基醇Schiff碱。对3-甲酰基-N-乙基咔唑中间体的合成条件进行了探索,发现N-乙基咔唑与POCl3和DMF的摩尔比为1:10:10时,单甲酰化的产率最高。
首次通过无溶剂法合成出了新型手性氨基醇类Schiff碱,研究了THF、无水乙醇、冰醋酸和无水乙醇-冰醋酸等溶剂体系以及无溶剂体系对目标手性氨基醇Schiff碱产率的影响。通过实验探究,发现采用溶剂体系时,反应条件温和,但目标手性氨基醇Schiff碱难于提纯;采用无溶剂法合成目标手性氨基醇Schiff碱,缩短了反应时间,无需添加催化剂,用混合溶剂重结晶便能使产物与杂质分离,纯度和产率颇高。当反应时间为40min、反应温度为95℃时大部分目手性氨基醇标Schiff碱的合成产率可达87%以上。
研究了氨基醇的结构对目标手性氨基醇Schiff碱的紫外光谱和发光性能的影响。发现氨基醇的结构对目标手性氨基醇Schiff碱的荧光光谱有明显的影响。通过荧光光谱分析发现Schiff碱L1的发光性能最好,其主要原因为苯丙氨醇存在芳环,使其分子结构具有良好的共轭性,增强了它的能量传递效率,导致其荧光强度增加。
(2)以咔唑、2-萘酚、水杨酸甲酯、对硝基苯甲酸、苯甲酸乙酯为原料,合成出了9个新的含咔唑基双酰腙类Schiff碱。探究了N-烷基咔唑的Friedel—Crafts酰基化反应和目标双酰腙类Schiff碱的合成条件,发现当N-烷基咔唑、乙酰氯和催化剂的摩尔比为1:5:4时,3,6-二乙酰基-N-烷基咔唑中间体的产率最高;当无水乙醇与冰醋酸的体积比为10:2时,目标双酰腙类Schiff碱的产率最高。研究了目标酰腙类Schiff碱的光谱性能,发现Schiff碱L7和L8具有较好的荧光性能。
Schiff base is a class of organic compounds which contain characteristic imine or azomethine group (-C=N-). The Schiff base aroused the interest of scholars both home and abroad, because of its various coordination forms, strong coordination ability, good biological activities and optical properties. Some of them have been widely applied in medicine, catalysis and photoelectric materials. In this paper, fifteen novel carbazol-containing Schiff bases were synthesized, and also characterized by 1H NMR, MS, IR, and elemental analyses. The works mainly include:
(1) The chiral amino alcohols and 3-formacyl-N-ethyl carbazole as the key intermediates were synthesized with the carbazole and natural amino-acid as the materials, and the synthesis conditions of 3-formacyl-N-ethyl carbazole were optimizated. The results show that the best yield of sing-formylation was obtained, when the volume ratio of N-ethyl carbazole, POCl3 and DMF is 1:10:10.
Six novel chiral amino alcohol Schiff bases were synthesized by the solvent-free reaction for the first time. The influence of the different organic solvent system (THF, EtOH, AcH, EtOH-AcH) and solvent-free system on the yields of the target chiral amino alcohol Schiff bases was studied in detail. The experimental results show that the synthesis conditions of the target chiral amino alcohol Schiff bases are mild in the organic solvent system, but the products are purified very difficultly. Compared with the previous method, the solvent-free method possess such advantages as short reaction time, without adding catalyst, high yield and only simple recrystallization purification in mixed solvent. The yield of the target chiral amino alcohol Schiff base was up to 87%, when the reaction temperature was at 95℃and the reaction time was 40 min.
The effect of the structure of the chiral amino alcohol on the spectral propertie of the target chiral amino alcohol Schiff bases was studied. The results indicat that the structure of the chiral amino alcohol have significant influence on their fluorescence, and the Schiff base L1 has the best fluorescence intensity. Because L-phenylglycinol possesses the aromatic rings, the conjugation effect of the molecular structure of the Schiff base L1 are improved, and its energy transfer efficiency is enhanced, its fluorescence intensity is increased.
(2) Nine novel carbazol-containing diacylhydrazone Schiff bases were synthesized with the carbazole, 2-naphthol, methyl salicylate, p-nitrobenzoic acid, and ethyl benzoate as the raw materials. And explored were the synthesis conditions of Friedel-Crafts acylation of N-alkyl carbazole and carbazol-containing diacylhydrazone Schiff bases. The experimental results show that the best yield of di-acetylation is obtained when the volume ratio of 9-alkyl carbazole, acetyl chloride, and catalyst is 1:5:4; the best yields of the target diacylhydrazone Schiff base is obtained when the volume ratio of ethanol and glacial acetic acid is 10:2. The spectral propertie of the target diacylhydrazone Schiff bases was studied, and the results indicat that Schiff base L7 and L8 have the best fluorescence intensity.
引文
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