CN106810581A - 一种硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物及其合成方法和应用 - Google Patents
一种硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物及其合成方法和应用 Download PDFInfo
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Abstract
本发明涉及一种硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物及其制备方法和应用。本发明将水杨醛类希夫碱引入到硫代杯[4]芳烃的下缘，形成下垂螯合臂，利用其与硫代杯芳烃空穴的协同作用，增加所得硫代杯芳烃衍生物对的金属Co离子的配位能力。并对合成得到的水杨醛类席夫碱化合物对催化分解H2O2的催化性能进行初步研究。结果表明，合成得到的水杨醛类席夫碱Co配合物具有很强的分解H2O2的催化能力。
Description
技术领域
本发明涉及一种硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物及其合成方法和应用。
背景技术
近年来出现的硫代杯芳烃是杯芳烃家族的新成员，由于其用硫原子取代了传统杯芳烃的亚甲基桥，使芳香大环结构的刚性、极性都发生了较大的变化，有了较大的洞穴结构、构象更加灵活易变、显著的络合能力及硫桥易氧化等，尤其是构象的灵活易变引起了人们十分浓厚的兴趣。
希夫碱是一类含有碳氮双键官能团的高性能有机配体，该配体多数以氮原子和氧原子为配位原子，这与生物环境较为接近，所以备受人们的广泛关注。研究结果表明，希夫碱可与多种金属配位制备结构新颖、性能独特的希夫碱金属配合物，其金属配合物在药物、催化、农药、新材料等领域都有广泛的应用。
发明内容
针对上述现有技术，本发明提供了一种硫代杯芳烃希夫碱双核钴配位化合物，及其制备方法，并公开了其在催化分解H2O2的催化方面的应用。
本发明采用的技术方案是：一种硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物，其结构式如下所示：
所述的硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物的制备方法，其特征在于：所述方法包括以下步骤：
（1）硫代杯[4]芳烃和O-(氯丁基)- 水杨醛在催化剂碘化钾和无水碳酸钾的存在下，在干燥乙腈溶剂中回流反应，4-5天后停止，抽滤，将滤液减压蒸馏大部分溶剂后，加入无水乙醇，发现有固体析出，所得固体经重结晶后，得到硫代杯[4]芳烃水杨醛衍生物；
所述的硫代杯[4]芳烃和O-(氯丁基)- 水杨醛的物质的量之比为：1:4～5；
（2）将步骤（1）中的硫代杯[4]芳烃水杨醛衍生物与2-氨基-2-乙基-1,3-丙二醇加热溶解在干燥乙腈溶剂中，滴加盐酸作为催化剂，室温条件下搅拌2天，逐渐有固体析出，滤出固体，重结晶，得到硫代杯[4]芳烃水杨醛类希夫碱配体；
其中硫代杯[4]芳烃水杨醛衍生物与2-氨基-2-乙基-1,3-丙二醇的物质的量比为：1:3～4；
（3）将步骤（2）中的硫代杯[4]芳烃水杨醛类希夫碱配体溶于N,N-二甲基甲酰胺中至其完全溶解，滴加Co（NO2）2·6H2O的无水甲醇溶液，在转速为260r/min，滴加速度为6～8ml/min边搅拌边滴加，90～100oC加热搅拌至混合溶液反应完全，待反应完全后冷却至室温，静置1～2小时，抽滤，再用去离子水洗涤，50oC真空干燥4～5小时，制备成硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物；
其中硫代杯[4]芳烃水杨醛类希夫碱配体与Co（NO2）2·6H2O的物质量比为1：（4～5）；
所述Co（NO2）2·6H2的无水甲醇溶液中，Co（NO2）2·6H2的浓度为21.8～29.1g/L。
本发明将水杨醛类希夫碱引入硫代杯[4]芳烃的下缘，利用其与硫杯芳烃空穴的协同作用，增加所得硫代杯芳烃衍生物对金属Co离子的选择性络合能力。通过对化合物性质进行初步测定，结果发现化合物对金属Co离子具有较好的识别功能，并对合成得到的水杨醛类席夫碱化合物对催化分解H2O2的催化性能进行初步研究。结果表明，合成得到的水杨醛类席夫碱双核钴配合物具有很强的分解H2O2的催化能力。
具体实施方式
下面通过具体实施例对本发明的合成方法进一步说明。
实施例1：硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物的方法包括以下步骤;
[1]制备硫代杯[4]芳烃水杨醛衍生物
硫代杯[4]芳烃(4.0g，5.6mmol)和O-(氯丁基)-水杨醛(7.4 g，28.0mmol)在催化剂碘化钾(0.9g，6.0mmol)和无水碳酸钾(6.0g，43.5mmol)的存在下，在干燥乙腈溶剂中回流反应，4-5天后停止，抽滤，将滤液减压蒸馏大部分溶剂后，加入无水乙醇，发现有固体析出，所得固体用氯仿/乙醇（体积比3:1）重结晶后，得到白色固体，产率64%。
[2]制备硫代杯[4]芳烃水杨醛类希夫碱配体
取步骤[1]中硫代杯[4]芳烃水杨醛衍生物(1.6g，1.0mmol)与2-氨基-2-乙基-1,3-丙二醇(0.6g，4.0mmol)加热溶解在干燥乙腈溶剂中，滴加一滴盐酸作为催化剂，室温条件下搅拌2天，逐渐有固体析出，滤出固体，固体用氯仿/乙醇（体积比3:1）重结晶，得到硫代杯[4]芳烃水杨醛类希夫碱配体。
IR(KBr) v: 3667(m), 2956(s), 2869(m), 1671(vs), 1598(w), 1509(s),1467(w), 1382(w), 1268(vs), 1140(m), 1036(s), 997(m), 814(w), 801(s), 750(m),703(m), 690(w), 537(m)cm-1;
[3] 制备硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物
将步骤（2）中的硫代杯[4]芳烃水杨醛类希夫碱配体(1.9g，1.0mmol)溶于N,N-二甲基甲酰胺中至其完全溶解，滴加Co（CH3CO2）2·H2O(1.9g，1.0mmol)的无水甲醇溶液（10mL），在转速为260r/min，滴加速度为6～8ml/min边搅拌边滴加，90～100oC加热搅拌至混合溶液反应完全，待反应完全后冷却至室温，静置1～2小时，抽滤，再用去离子水洗涤，50oC真空干燥4～5小时，制备成硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物，产率78%。
产物经红外光谱分析和元素分析，结果如下：
元素分析：C112H128N4O12Co2：计算值：C 72.72，H 6.92，N4.17%；实侧值：C 72.61，H6.83，N4.22%。
硫代杯芳烃Schiff碱的每个分子中含有一个Schiff碱单元，因此两分子硫代杯芳烃Schiff碱可以和金属形成配合物。配体中有1090左右的峰，为C=N的伸缩振动，但配合物的IR谱中，此谱带消失或红移，这是说明C=N参与了配位，1595cm-1，1508cm-1，1468cm-1处的峰为苯环的骨架震动峰；1266cm-1处的峰为碳-氮键单键的伸缩振动峰。通过元素分析和红外光谱分析表明，该产物的组成为
C112H128N4O12Co2。
实施例2：称取硫代杯[4]芳烃水杨醛类希夫碱配体（1a）及其双核钴配合物（和Ⅱa）和Co（CH3CO2）2·4H2O的DMSO溶液1mL作为催化剂，加入15%的双氧水20mL，室温（20oC）放置1d。然后用高锰酸钾标准溶液滴定并计算双氧水分解百分率。测硫代杯[4]芳烃水杨醛类希夫碱配体（1a）及其双核钴配合物（和Ⅱa）和Co（CH3CO2）2·H2O催化剂的催化分解率（表1）。
| 化合物 | |
| 79.4 | |
| 1a | 0 |
| Ⅱa | 97.6 |
由表1可知，在相同的浓度的催化剂中，乙酸钴和硫代杯[4]芳烃水杨醛类希夫碱配体双核钴配合物对双氧水分解均有一定的催化作用，而硫代杯[4]芳烃水杨醛类希夫碱配体不具有催化剂双氧水分解的性质。并且硫代杯[4]芳烃水杨醛类希夫碱配体双核钴配合物催化剂能较金属盐好的多。
Claims (2)
1.一种硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物,其特征在于结构式如下所示：
。
2.权利要求1所述的硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物的制备方法，其特征在于：所述方法包括以下步骤：
（1）硫代杯[4]芳烃和O-(氯丁基)- 水杨醛在催化剂碘化钾和无水碳酸钾的存在下，在干燥乙腈溶剂中回流反应，4-5天后停止，抽滤，将滤液减压蒸馏大部分溶剂后，加入无水乙醇，发现有固体析出，所得固体经重结晶后，得到硫代杯[4]芳烃水杨醛衍生物；
其中硫代杯[4]芳烃和O-(氯丁基)- 水杨醛的物质的量之比为：1:4～5；
（2）将步骤（1）中的硫代杯[4]芳烃水杨醛衍生物与2-氨基-2-乙基-1,3-丙二醇加热溶解在干燥乙腈溶剂中，滴加盐酸作为催化剂，室温条件下搅拌2天，逐渐有固体析出，滤出固体，重结晶，得到硫代杯[4]芳烃水杨醛类希夫碱配体；
其中硫代杯[4]芳烃水杨醛衍生物与2-氨基-2-乙基-1,3-丙二醇的物质的量比为：1:3～4；
（3）将步骤（2）中的硫代杯[4]芳烃水杨醛类希夫碱配体溶于N,N-二甲基甲酰胺中至其完全溶解，滴加Co（NO2）2·6H2O的无水甲醇溶液，在转速为260r/min，滴加速度为6～8ml/min边搅拌边滴加，90～100oC加热搅拌至混合溶液反应完全，待反应完全后冷却至室温，静置1～2小时，抽滤，再用去离子水洗涤，50oC真空干燥4～5小时，制备成硫代杯[4]芳烃水杨醛类希夫碱双核钴配位化合物；
其中硫代杯[4]芳烃水杨醛类希夫碱配体与Co（NO2）2·6H2O的物质量比为1：（4～5）；
所述Co（NO2）2·6H2O的无水甲醇溶液中，Co（NO2）2·6H2O的浓度为21.8～29.1g/L 。
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108314690A (zh) * | 2018-03-15 | 2018-07-24 | 中国科学院苏州生物医学工程技术研究所 | 双杯[4]芳烃衍生物的金属配合物及其合成方法和应用 |
| CN113999393A (zh) * | 2021-11-22 | 2022-02-01 | 南京大学 | 一种聚多巴胺席夫碱-铜配合物催化剂及其制备方法与应用 |
| CN115252869A (zh) * | 2022-08-18 | 2022-11-01 | 南通大学 | 一种促进血管再生的纳米敷料及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108314690A (zh) * | 2018-03-15 | 2018-07-24 | 中国科学院苏州生物医学工程技术研究所 | 双杯[4]芳烃衍生物的金属配合物及其合成方法和应用 |
| CN108314690B (zh) * | 2018-03-15 | 2019-06-07 | 中国科学院苏州生物医学工程技术研究所 | 双杯[4]芳烃衍生物的金属配合物及其合成方法和应用 |
| CN113999393A (zh) * | 2021-11-22 | 2022-02-01 | 南京大学 | 一种聚多巴胺席夫碱-铜配合物催化剂及其制备方法与应用 |
| CN113999393B (zh) * | 2021-11-22 | 2022-09-02 | 南京大学 | 一种聚多巴胺席夫碱-铜配合物催化剂及其制备方法与应用 |
| CN115252869A (zh) * | 2022-08-18 | 2022-11-01 | 南通大学 | 一种促进血管再生的纳米敷料及其制备方法 |
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