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首页> 外文期刊>Catalysis science & technology >Fluorescence spectroscopy studies of crossed aldol reactions: a reactive Nile red dye reveals catalyst-dependent product formation
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Fluorescence spectroscopy studies of crossed aldol reactions: a reactive Nile red dye reveals catalyst-dependent product formation

机译：荧光光谱的研究跨越了醇醛反应:反应尼罗红染色显示catalyst-dependent产品形成

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The synthesis of a new Nile red derivative incorporating a reactive aldehyde moiety (NR-CHO) is reported and its use in spectroscopic studies of heterogeneous catalyst activity in crossed aldol reactions is demonstrated.H-1 and(13)C NMR, and high-resolution mass spectrometry confirmed the desired NR-CHO was obtained. Mg-Zr-Cs doped silica (Cs(Zr,Mg)-SiO2) was employed as the catalyst and its performance was compared to that of commercially available MgO. Fumed silica was used as a control. Aldol reactions with acetone and acetophenone were run in 4 : 1 (v/v) DMSO : ketone solutions in the presence of both dilute (1 mu M) and concentrated (1 mM) NR-CHO. NR-CHO fluorescence spectra were acquired as the reactions progressed. Shifts in its emission spectrum are used to distinguish the products formed and to characterize the reaction rate. The dye exhibits different behavior that defines whether the reaction stops at the addition (alcohol) product, or forms both addition and condensation (olefin) products, providing valuable initial information on catalyst activity. The assignment of addition and condensation products is supported by thin layer chromatography, high performance liquid chromatography (HPLC), and HPLC-mass spectrometry data. Product formation is shown to depend upon the catalyst employed, with the Cs(Zr,Mg)-SiO(2)yielding both addition and condensation products, while MgO yields primarily addition products. The advantages of NR-CHO in spectroscopic studies of aldol reactions are also demonstrated relative to commercially available 3-perylenecarboxaldehyde. The NR-CHO reported here and the results obtained will facilitate a broad range of both ensemble and single molecule spectroscopic investigations of heterogeneous catalysis in crossed aldol reactions in the future.
机译：合成一个新的尼罗红的导数将被动醛一半(NR-CHO)据报道及其使用光谱研究多相催化活动的交叉醇醛反应demonstrated.H-1 (13) C核磁共振,和高分辨率质谱证实所需的NR-CHO。硅(Cs(锆、毫克)二氧化硅)的催化剂及其性能进行了比较商业上可用的分别。作为一个控制。和苯乙酮是运行在4:1 (v / v) DMSO溶液:酮溶液的稀释(1μM)和集中(1毫米)NR-CHO。荧光光谱被收购了反应的进展。光谱是用来区分产品形成和反应速率的特点。定义染料表现出不同的行为是否反应停在增加(酒精)产品,或添加和形式冷凝(烯烃)产品,提供有价值的催化剂的初步信息活动。冷凝产品支持薄层高效液相色谱法色谱法(HPLC)和HPLC-mass谱分析数据。使用的催化剂,Cs(锆、毫克)-SiO加法和(2)的收益率冷凝产品,分别以产量为主添加产品。光谱的研究醇醛反应也相对于商用演示3-perylenecarboxaldehyde。这里获得的结果将帮助广泛的合奏和单分子光谱的研究异构交叉羟醛反应的催化作用的未来。

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