CN107686453A - 邻羧基苯甲醛缩乙二胺席夫碱铜配合物的制备方法 - Google Patents
邻羧基苯甲醛缩乙二胺席夫碱铜配合物的制备方法 Download PDFInfo
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Abstract
本发明公开了一种邻羧基苯甲醛缩乙二胺席夫碱铜配合物的制备方法。以邻羧基苯甲醛和乙二胺为原料，冰醋酸为催化剂，无水甲醇为溶剂，经溶液法制备邻羧基苯甲醛缩乙二胺席夫碱；再以邻羧基苯甲醛缩乙二胺席夫碱和一水合乙酸铜为原料，无水甲醇为溶剂，经水热法制备邻羧基苯甲醛缩乙二胺席夫碱铜配合物。本发明方法具有工艺简单、重现性好、产率较高的优点，且制得的邻羧基苯甲醛缩乙二胺席夫碱及其铜配合物均具有荧光性质，在荧光探针、荧光分析领域具有潜在的应用价值。
Description
技术领域
本发明涉及一种双席夫碱，具体涉及一种邻羧基苯甲醛缩乙二胺席夫碱铜配合物的制备方法。
背景技术
席夫碱是由含伯氨基与活泼羰基的两类物质通过缩合反应生成的含有亚胺（-CH=N-）或甲亚胺（-CR=N-）基团的一类化合物。席夫碱按不同分类方法有不同的类型，按构造式划分，可分为单席夫碱、双席夫碱、大环类席夫碱、杂环席夫碱等；按基团配位模式划分，可分为缩胺类、缩酮类等；按配位金属的不同可分为单核、多核等。由于席夫碱分子中含有C=N键，不仅含有不饱和双键，氮原子还能提供孤对电子，所以其具有较强的反应活性，能够对取代基给予体的类型和位置进行不同的转变，从而能够衍生出功能不同、构造多变的席夫碱及其配合物。
席夫碱因其结构特点在诸多领域具有重要的研究价值，是近年来科学工作者研究的热点之一。其中缩氨基脲类、吡唑类、酰腙类、酰肼类的席夫碱研究的比较多，特别是水杨醛类、含多羟基类的席夫碱，而含羧基的双席夫碱目前鲜有报道。芳香族双席夫碱类化合物，含有共轭大π键，可有效的吸收紫外光，从而使物质具有一定的荧光性质。含羧基的配体配位模式相对灵活，除能提高配位能力外，还具有结构稳定等特点。由于结构的独特性，使这类席夫碱受到人们的广泛关注。
本申请利用邻羧基苯甲醛与乙二胺反应合成了一种新型双席夫碱，以该双席夫碱为配体合成了一种铜配合物，并通过晶体结构、核磁共振氢谱、红外光谱、紫外光谱等测试方法对席夫碱配体及其铜配合物进行结构表征，确定合成产物为目标产物，并研究了该席夫碱和铜配合物的荧光性质。
发明内容
本发明的目的是提供一种邻羧基苯甲醛缩乙二胺席夫碱铜配合物的制备方法。
具体步骤为：
（1）称取1.5000 g（10.0 mmol）邻羧基苯甲醛和10 mL无水甲醇，加入到100 mL的三口烧瓶中，磁力搅拌，制得无色透明清液。
（2）称取0.3700 g（5.0 mmol）乙二胺溶入5 mL无水甲醇中，所得溶液滴加到步骤（1）制得的无色透明清液中，滴加完毕后，加入0.15 mL冰醋酸作为催化剂，在氮气保护、50℃下，回流搅拌反应4小时后，有白色沉淀生成，趁热过滤，获得沉淀，用无水甲醇洗涤该沉淀3次，每次无水甲醇的用量为10 mL，然后干燥，得到白色粉末，即为邻羧基苯甲醛缩乙二胺席夫碱。
（3）称取0.1 g（0.1 mmol）步骤（2）中制得的邻羧基苯甲醛缩乙二胺席夫碱，溶于5mL 的N,N-二甲基甲酰胺（DMF）中，待全部溶解之后转移至试管中，再取5 mL乙腈，沿试管壁滴入，封好试管，在阴暗处静置3天，试管底部有白色块状晶体析出，即为邻羧基苯甲醛缩乙二胺席夫碱晶体。
（4）称取0.0648 g（0.2 mmol）步骤（3）制得的邻羧基苯甲醛缩乙二胺席夫碱晶体溶于8 mL无水甲醇，室温磁力搅拌下，滴加入含有0.0399 g（0.2 mmol）一水合乙酸铜的8mL无水甲醇溶液，搅拌1小时后，转入带有聚四氟乙烯瓶的反应釜中，放入100 ℃烘箱中，2小时之后关闭烘箱，自然冷却至室温，过滤，其滤液在室温下静置自然挥发，3天后有蓝色片状晶体析出，再过滤，用DMF洗涤3次，再用无水甲醇洗涤3次，每次DMF和无水甲醇的用量均为10 mL，再放入30 ℃真空干燥箱中，干燥24小时，即制得邻羧基苯甲醛缩乙二胺席夫碱铜配合物晶体。
本发明方法具有工艺简单、重现性好、产率较高的优点，且制得的邻羧基苯甲醛缩乙二胺席夫碱及其铜配合物均具有荧光性质，在荧光探针、荧光分析领域具有潜在的应用价值。
附图说明
图1 为本发明实施例中制得的邻羧基苯甲醛缩乙二胺席夫碱的晶体结构图。
图2 为本发明实施例中制得的邻羧基苯甲醛缩乙二胺席夫碱铜配合物的晶体结构图。
图3为本发明实施例中制得的邻羧基苯甲醛缩乙二胺席夫碱的荧光光谱。
图4为本发明实施例中制得的邻羧基苯甲醛缩乙二胺席夫碱铜配合物的荧光光谱。
具体实施方式
实施例：
下面结合具体实施例进一步阐明本发明，但实施例并不限制本发明的保护范围。
（1）称取1.5000 g（10.0 mmol）邻羧基苯甲醛和10 mL无水甲醇，加入到100 mL的三口烧瓶中，磁力搅拌，制得无色透明清液。
（2）称取0.3700 g（5.0 mmol）乙二胺溶入5 mL无水甲醇中，所得溶液滴加到步骤（1）制得的无色透明清液中，滴加完毕后，加入0.15 mL冰醋酸作为催化剂，在氮气保护、50℃下，回流搅拌反应4小时后，有白色沉淀生成，趁热过滤，获得沉淀，用无水甲醇洗涤该沉淀3次，每次无水甲醇的用量为10 mL，然后干燥，得到白色粉末，即为邻羧基苯甲醛缩乙二胺席夫碱。
（3）称取0.1 g（0.1 mmol）步骤（2）中制得的邻羧基苯甲醛缩乙二胺席夫碱，溶于5mL 的N,N-二甲基甲酰胺（DMF）中，待全部溶解之后转移至试管中，再取5 mL乙腈，沿试管壁滴入，封好试管，在阴暗处静置3天，试管底部有白色块状晶体析出，即为邻羧基苯甲醛缩乙二胺席夫碱晶体。
（4）称取0.0648 g（0.2 mmol）步骤（3）制得的邻羧基苯甲醛缩乙二胺席夫碱晶体溶于8 mL无水甲醇，室温磁力搅拌下，滴加入含有0.0399 g（0.2 mmol）一水合乙酸铜的8mL无水甲醇溶液，搅拌1小时后，转入带有聚四氟乙烯瓶的反应釜中，放入100 ℃烘箱中，2小时之后关闭烘箱，自然冷却至室温，过滤，其滤液在室温下静置自然挥发，3天后有蓝色片状晶体析出，再过滤，用DMF洗涤3次，再用无水甲醇洗涤3次，每次DMF和无水甲醇的用量均为10 mL，再放入30 ℃真空干燥箱中，干燥24小时，即制得邻羧基苯甲醛缩乙二胺席夫碱铜配合物晶体，产率为28.53 %。M.P.：253 ℃～260 ℃。
通过单晶 X-射线衍射对本实施例制得的邻羧基苯甲醛缩乙二胺席夫碱和邻羧基苯甲醛缩乙二胺席夫碱铜配合物的晶体结构进行解析，确定二者的结构。由附图1可知，邻羧基苯甲醛缩乙二胺席夫碱是由一个乙二胺分子和两个邻羧基苯甲醛发生缩合反应，脱掉2个水分子而成。由于反应条件的特异性，邻羧基苯甲醛双席夫碱中的C=N双键与邻位-COOH反应成环，形成了一个新型对称四环化合物。由邻羧基苯甲醛缩乙二胺席夫碱铜配合物的晶体结构图（附图2）可知，每个晶胞含有两个配合物分子。以其中一个配合物分子为例进行分析。该铜配合物是由两个铜离子和两个配体、一个共用的游离甲醇分子、一个游离的水分子构成。在配合物中，每个铜离子均为+2价。每个铜离子均处于相同的五配位环境中，呈中心对称，铜离子分别与来自一个配体上羧基的两个氧原子和两个氮原子，另一个配体羧基上的氧原子配位。配位原子N14，O1，O1i（对称码：(i) −x+1, −y+1, −z+1.）与中心铜离子形成的键角之和为346.2°，表明三个配位原子位于一个近似的平面内，O6原子和N15原子位于三角双锥的两个顶点，形成了一个五配位的三角双锥CuO3N2构型。
利用日本日立高科技公司的F-4600型荧光光谱仪，以DMF为参比液，在室温下对本实施例制得的邻羧基苯甲醛缩1,3-丙二胺席夫碱及其铜配合物的DMF溶液（浓度为1.0×10-5 mol/L）的荧光发射光谱（激发和发射狭缝宽度各为10 nm）进行了测试，结果表明，邻羧基苯甲醛缩乙二胺席夫碱及其铜配合物能发射荧光，其中邻羧基苯甲醛缩乙二胺席夫碱最大发射波长为327 nm，其激发波长为305 nm，而铜配合物的最大发射波长为323nm，其激发波长为324 nm。
附图3和附图4为本实施例制得的邻羧基苯甲醛缩乙二胺席夫碱配体及其铜配合物的荧光光谱。邻羧基苯甲醛缩乙二胺席夫碱的发射荧光可归因于配体π-π*电子转移跃迁。铜配合物发射荧光可归因于配体与金属离子之间发生LMCT或MLCT的电子转移跃迁或配体π-π*电子转移跃迁。配合物和配体相比，其发射波长均发生不同程度的蓝移，可能是因为配体与金属离子配位后，导致HOMO-LUMO能级差增大。配合物的荧光强度较配体有明显的降低，荧光强度减弱的原因，可能是形成双核铜配合物后，增加了-COOR吸电子基团，使荧光强度明显降低。
Claims (1)
1.一种邻羧基苯甲醛缩乙二胺席夫碱铜配合物的制备方法，其特征在于具体步骤为：
（1）称取10.0 mmol邻羧基苯甲醛和10 mL无水甲醇，加入到100 mL的三口烧瓶中，磁力搅拌，制得无色透明清液；
（2）称取5.0 mmol乙二胺溶入5 mL无水甲醇中，所得溶液滴加到步骤（1）制得的无色透明清液中，滴加完毕后，加入0.15 mL冰醋酸作为催化剂，在氮气保护、50 ℃下，回流搅拌反应4小时后，有白色沉淀生成，趁热过滤，获得沉淀，用无水甲醇洗涤该沉淀3次，每次无水甲醇的用量为10 mL，然后干燥，得到白色粉末，即为邻羧基苯甲醛缩乙二胺席夫碱；
（3）称取0.1 mmol步骤（2）中制得的邻羧基苯甲醛缩乙二胺席夫碱，溶于5 mL 的N,N-二甲基甲酰胺中，待全部溶解之后转移至试管中，再取5 mL乙腈，沿试管壁滴入，封好试管，在阴暗处静置3天，试管底部有白色块状晶体析出，即为邻羧基苯甲醛缩乙二胺席夫碱晶体；
（4）称取0.2 mmol步骤（3）制得的邻羧基苯甲醛缩乙二胺席夫碱晶体溶于8 mL无水甲醇，室温磁力搅拌下，滴加入含有0.2 mmol一水合乙酸铜的8 mL无水甲醇溶液，搅拌1小时后，转入带有聚四氟乙烯瓶的反应釜中，放入100 ℃烘箱中，2小时之后关闭烘箱，自然冷却至室温，过滤，其滤液在室温下静置自然挥发，3天后有蓝色片状晶体析出，再过滤，用N,N-二甲基甲酰胺洗涤3次，再用无水甲醇洗涤3次，每次N,N-二甲基甲酰胺和无水甲醇的用量均为10 mL，再放入30 ℃真空干燥箱中，干燥24小时，即制得邻羧基苯甲醛缩乙二胺席夫碱铜配合物。
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| CN109134359A (zh) * | 2018-09-06 | 2019-01-04 | 桂林理工大学 | 一种2,6-二氨基吡啶缩乙醛酸双席夫碱缓蚀剂的制备方法 |
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| CN109134299A (zh) * | 2018-09-06 | 2019-01-04 | 桂林理工大学 | 一种1,2-丙二胺缩5-氟水杨醛双席夫碱缓蚀剂的制备方法 |
| CN109134359A (zh) * | 2018-09-06 | 2019-01-04 | 桂林理工大学 | 一种2,6-二氨基吡啶缩乙醛酸双席夫碱缓蚀剂的制备方法 |
| CN109134359B (zh) * | 2018-09-06 | 2022-03-22 | 桂林理工大学 | 一种2,6-二氨基吡啶缩乙醛酸双席夫碱缓蚀剂的制备方法 |
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