含咪唑环的功能化合物的合成研究与发光性能的测定
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摘要
咪唑是重要的富π电子杂环化合物之一，具有两性，能传递电子和质子，热稳定性好，化学性质活泼，是许多酶的活性中心，具有优良的药学和与金属离子配位性能，因此，咪唑及其衍生物在医药、农药、材料、金属离子检测、有机合成、及其发光功能材料中用途广泛。本文所合成的化合物在以后的化工生产中将会带来更高的附加价值，并具有很好的应用前景。
本论文以芳香醛为原料，在维生素B1作用下，经安息香缩合反应制得相应的2-羟基-1,2-二芳基乙酮。再以此为原料与不同的酰化试剂酯化生成偶姻酯。然后运用了备受研究者青睐的微波辅助法，以偶姻酯为原料，在无溶剂条件下合成三取代咪唑。进而以三取代咪唑为原料，研究了三取代咪唑和氯化苄的反应。
首先，以芳香醛为原料，通过相应的反应，以88.5%–96.2%的收率合成17种鲜见报道的偶姻单酯。
其次，将该偶姻酯与醋酸铵附着在固载体酸性氧化铝上，在无溶剂条件下微波加热以38.5%–83.3%合成了17种三取代咪唑，其中7种未见文献报道。证明了该反应的可行性，讨论了不同取代基对生成目的产物收率的影响规律。并通过IR、HRMS谱、~1H NMR和~(13)C NMR对所合成的产物分别进行表征分析，确定了所合成的化合物的结构式，并提出了可能的反应机理。
再次，在探究含有呋喃环的三取代咪唑与苄基化合物在无水四氢呋喃中反应时，成功地以59.0%~89.8%收率合成了15种鲜见报道的含呋喃环的四取代咪唑，并表征了其结构。
最后，因咪唑环的特殊性质，它可以作为优良的有机非线光学材料。所以研究了所合成化合物的发光性能，并计算得到荧光量子效率，得到了满意的结果。对所有化合物的紫外和荧光光谱数据分析，简单地讨论了取代基对其荧光性能的影响，为含呋喃环的咪唑衍生物进一步运用到光学材料中奠定了基础。
Imidazole is one of the most important heterocyclic compounds including rich πelectron, which is amphoteric compounds. Imidazole play an important role inbiochemistry, material chemistry including luminescent material and protonconductivity material, medicinal chemistry and the determination of heavy metal iondue to that possess good thermal stability, transmitting electrons and protons, highreactive active, and excellent pharmaceutical, etc. Herein, the synthesis oftri-substituted imidazole were explored from benzoin carboxylates. Futher, newtetra-substitutied imidazole derivative containing furan rings were synthesized. Thesesynthesized compounds will bring high value-added and bright application prospect inchemical production.
Firstly,2-hydroxy-1,2-diarylethanone were synthesized with the aromaticaldehydes as raw material in the presence of the catalyst VB1. And then,2-hydroxy-1,2-diarylethanone reacted with different acylating reagents under mildreaction conditions, benzoin carboxylates were obtained in excellent yields (88.5%–96.2%).
Secondly,2-substituted-4,5-di(aryl)imidazoles were produced from benzoincarboxylates on solid supports alumina as a dispersant impregnated with ammoniumacetate in the yield of38.5%–83.3%, and seven of them have not been reported. Thesynthesized compounds were characterized by IR, HRMS and1H and13C NMRspectral. All compounds were characterized to determine their structures and thereaction mechanism was proposed.
Thirdly,2-substituted-4,5-di(aryl)imidazoles as a material, to explore thenitrogen of trisubstituted imidazoles containing furan rings to introduce the fourthsubstituted groups. The reaction of trisubstituted imidazole and benzyl chloride inanhydrous THF was investigated, As a result, fifteen new imidazole compoundscontaining furan rings were synthesized in better yield59.0%~89.8%. Thesynthesized products were characterized by IR, elemental analysis, HRMS spectra,~1HNMR and~(13)C NMR.
In addition, Imidazole ring is considered as good organic non-linear opticalmaterial owing to its special nature. Therefore, the UV–vis and photoluminescencespectra of the synthesized compounds were mensurated, the fluorescence quantumyields were calculated, which is the groundwork for the further application of furanderivatives to optical materials.
本论文以芳香醛为原料，在维生素B1作用下，经安息香缩合反应制得相应的2-羟基-1,2-二芳基乙酮。再以此为原料与不同的酰化试剂酯化生成偶姻酯。然后运用了备受研究者青睐的微波辅助法，以偶姻酯为原料，在无溶剂条件下合成三取代咪唑。进而以三取代咪唑为原料，研究了三取代咪唑和氯化苄的反应。
首先，以芳香醛为原料，通过相应的反应，以88.5%–96.2%的收率合成17种鲜见报道的偶姻单酯。
其次，将该偶姻酯与醋酸铵附着在固载体酸性氧化铝上，在无溶剂条件下微波加热以38.5%–83.3%合成了17种三取代咪唑，其中7种未见文献报道。证明了该反应的可行性，讨论了不同取代基对生成目的产物收率的影响规律。并通过IR、HRMS谱、~1H NMR和~(13)C NMR对所合成的产物分别进行表征分析，确定了所合成的化合物的结构式，并提出了可能的反应机理。
再次，在探究含有呋喃环的三取代咪唑与苄基化合物在无水四氢呋喃中反应时，成功地以59.0%~89.8%收率合成了15种鲜见报道的含呋喃环的四取代咪唑，并表征了其结构。
最后，因咪唑环的特殊性质，它可以作为优良的有机非线光学材料。所以研究了所合成化合物的发光性能，并计算得到荧光量子效率，得到了满意的结果。对所有化合物的紫外和荧光光谱数据分析，简单地讨论了取代基对其荧光性能的影响，为含呋喃环的咪唑衍生物进一步运用到光学材料中奠定了基础。
Imidazole is one of the most important heterocyclic compounds including rich πelectron, which is amphoteric compounds. Imidazole play an important role inbiochemistry, material chemistry including luminescent material and protonconductivity material, medicinal chemistry and the determination of heavy metal iondue to that possess good thermal stability, transmitting electrons and protons, highreactive active, and excellent pharmaceutical, etc. Herein, the synthesis oftri-substituted imidazole were explored from benzoin carboxylates. Futher, newtetra-substitutied imidazole derivative containing furan rings were synthesized. Thesesynthesized compounds will bring high value-added and bright application prospect inchemical production.
Firstly,2-hydroxy-1,2-diarylethanone were synthesized with the aromaticaldehydes as raw material in the presence of the catalyst VB1. And then,2-hydroxy-1,2-diarylethanone reacted with different acylating reagents under mildreaction conditions, benzoin carboxylates were obtained in excellent yields (88.5%–96.2%).
Secondly,2-substituted-4,5-di(aryl)imidazoles were produced from benzoincarboxylates on solid supports alumina as a dispersant impregnated with ammoniumacetate in the yield of38.5%–83.3%, and seven of them have not been reported. Thesynthesized compounds were characterized by IR, HRMS and1H and13C NMRspectral. All compounds were characterized to determine their structures and thereaction mechanism was proposed.
Thirdly,2-substituted-4,5-di(aryl)imidazoles as a material, to explore thenitrogen of trisubstituted imidazoles containing furan rings to introduce the fourthsubstituted groups. The reaction of trisubstituted imidazole and benzyl chloride inanhydrous THF was investigated, As a result, fifteen new imidazole compoundscontaining furan rings were synthesized in better yield59.0%~89.8%. Thesynthesized products were characterized by IR, elemental analysis, HRMS spectra,~1HNMR and~(13)C NMR.
In addition, Imidazole ring is considered as good organic non-linear opticalmaterial owing to its special nature. Therefore, the UV–vis and photoluminescencespectra of the synthesized compounds were mensurated, the fluorescence quantumyields were calculated, which is the groundwork for the further application of furanderivatives to optical materials.
引文
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