CN106565722A - 两种铜钛菁金属有机配合物及其制备方法 - Google Patents

两种铜钛菁金属有机配合物及其制备方法 Download PDF

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CN106565722A
CN106565722A CN201610984646.7A CN201610984646A CN106565722A CN 106565722 A CN106565722 A CN 106565722A CN 201610984646 A CN201610984646 A CN 201610984646A CN 106565722 A CN106565722 A CN 106565722A
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complexes
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copper phthalocyanine
metal organic
chloroform
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丁茯
苏阳
蔡捷
王东平
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Shenyang University of Chemical Technology
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    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
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    • B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination
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    • B01J2531/16—Copper

Abstract

两种铜钛菁金属有机配合物及其制备方法，涉及两种配合物及其制备方法，本发明公开了两种新型铜钛菁有机配合物的制备方法及其在碳氮偶联反应的催化应用。该方法涉及金属有机化学、配位化学和催化领域。本发明中的两种金属有机配合物是以3‑烷氧基取代的邻苯二腈和3‑芳氧基取代的邻苯二腈为配体，与铜盐反应制备得到两个四取代的铜酞菁配合物，对配合物进行了核磁、质谱、红外、紫外测试表征。结果表明，两种配合物结构明确。将其应用于碳氮偶联反应的催化应用研究中发现，该类配合物催化碳氮偶联反应时，具有反应条件温和，后处理简单，催化活性高、选择性高的良好特性，是极具潜力的催化剂。

Description

两种铜钛菁金属有机配合物及其制备方法
技术领域
本发明涉及两种配合物及其制备方法，特别是涉及两种铜钛菁金属有机配合物及其制备方法。
背景技术
通过在酞菁骨架上引入具有较大空间位阻的取代基，使酞菁分子间的π-π相互作用减弱，有效地阻碍分子之间的聚集，有效地改善了铜酞菁的溶解性能。采用3-烷氧基取代的邻苯二腈和3-芳氧基取代的邻苯二腈与铜盐反应制备了两个四取代铜酞菁配合物。两种配合物均可溶于二氯甲烷、乙酸乙酯等有机溶剂，可应用于多个研究领域。合成的两个铜钛菁有机配合物催化碳氮偶联反应时，表现为催化活性高，反应时间短，条件温和，催化剂本身结构稳定。
铜酞菁在化学催化、光疗药物、导电性、液晶显示、光电效应、气体敏感效应、光变色等方面呈现出的优良性能，使其在光动力学治疗、催化剂、半导体材料、非线性光学材料等方面具有广泛应用。因此，铜酞菁化合物的合成具有重要的理论研究意义和实际应用价值。
由于分子间具有强相互作用，使得多数无取代酞菁及其金属配合物在有机溶剂中溶解度很低，从而限制其实际应用。若在酞菁分子上引入取代基团，特别引入具有大空间阻碍的取代基，可有效阻止分子的相互聚集，从而增强其在有机溶剂中的溶解度。因此，取代酞菁及其金属配合物成为研究的焦点。为了适应不同领域的特殊应用要求，通常要对酞菁金属配合物的分子结构进行适当的调整和修饰。
发明内容
本发明的目的在于提供两种铜钛菁金属有机配合物及其制备方法，本发明合成具有新型结构的铜钛菁有机配合物的制备方法，并将其应用于碳氮偶联催化反应。所得两种配合物在催化性能测试中表现出反应速率快，催化效率高，催化剂本身结构稳定。
本发明的目的是通过以下技术方案实现的：
两种铜钛菁金属有机配合物，两种配合物均以具有不同空间效应的配体与铜化合物反应，得到铜酞菁；通过在酞菁骨架上引入具有较大空间位阻的取代基，使酞菁分子间的π-π相互作用减弱，阻碍分子之间的聚集，改善铜酞菁的溶解性能；两种铜钛菁配合物结构如下所示：
两种铜钛菁金属有机配合物的制备方法，所述方法包括以下制备步骤：
a) 配体3-（2,4-二甲基-3-戊氧基）邻苯二腈的合成
量取30ml的DMF加入到150ml的反应瓶中，冰水浴，保持温度3℃以下；氩气保护下，称取NaH加入到DMF中，搅拌10min；称取2,4-二甲基-3-戊醇滴加到上述溶液中，搅拌1.5h；称取3-硝基邻苯二腈溶于10ml DMF后，滴加入上述反应液中，反应1h，移除冰水浴；静置片刻，倒入500ml水，有大量棕色固体析出；减压抽滤，水洗三次；将所得固体溶于氯仿，以硫酸钠干燥；干燥后产品以氯仿为洗脱剂，柱层析法纯化；纯化得到的有色产品中加入石油醚，减压抽滤，用石油醚润洗除去杂色，干燥，称重；
b) 铜酞菁1的合成
在氩气氛下，150 mL反应瓶中，依次按比例加入3-（2,4-二甲基-3-戊氧基）邻苯二腈、尿素、钼酸铵、氯化亚铜，硝基苯，160℃搅拌反应；反应初始为淡黄色溶液，160℃后，有墨绿色粘稠状物质生成，溶液变为棕色，2.5hr后溶液颜色变墨绿，且颜色不再改变；反应结束后，减压蒸馏，以正己烷、氯仿为洗脱剂，柱层析法纯化，干燥，称重；
c) 3-(对叔丁基苯氧基）邻苯二腈配体的合成
在150 mL反应瓶内称取3-硝基邻苯二腈、对叔丁基苯酚、 K2CO3，及20ml DMSO混合反应；溶液颜色由橘黄色渐变为橘红色；反应结束过滤，产品加入DMSO，磁力搅拌1h，抽滤，依次用水、氯仿洗涤，以硫酸钠干燥；干燥后产品以氯仿为洗脱剂，柱层析法纯化。干燥，称重；
d)铜酞菁2的合成
在150mL反应瓶中依次加入3-(对叔丁基苯氧基）邻苯二腈配体、尿素、钼酸铵、氯化亚铜、硝基苯为溶剂，165℃反应；反应初始溶液为黄色溶液，165℃后，溶液依次变为橘黄色、棕色、黑色，蓝黑色后，颜色不再发生改变；反应结束后，减压蒸馏；所得固体以氯仿为洗脱剂，柱层析法提纯，干燥，称重；
e)铜钛菁的催化性能测试
在氩气保护下，以卤化物、氮杂环化合物为底物，DMSO为溶剂，加入KOH，2％mmol的催化剂，反应2.5h，用水:乙酸乙酯=3:10萃取，无水Na2SO4干燥.以乙酸乙酯、石油醚为洗脱剂，柱层析法纯化得目标产物；
。
本发明的优点与效果是：
本发明公开了两种新型铜钛菁有机配合物的制备方法及其在碳氮偶联反应的催化应用。该方法涉及金属有机化学、配位化学和催化领域。本发明中的两种金属有机配合物是以3-烷氧基取代的邻苯二腈和3-芳氧基取代的邻苯二腈为配体，与铜盐反应制备得到两个四取代的铜酞菁配合物，对配合物进行了核磁、质谱、红外、紫外测试表征。结果表明，两种配合物结构明确。将其应用于碳氮偶联反应的催化应用研究中发现，该类配合物催化碳氮偶联反应时，具有反应条件温和，后处理简单，催化活性高、选择性高的良好特性，是极具潜力的催化剂。
附图说明
图1配体3-（2,4-二甲基-3-戊氧基）邻苯二腈的核磁共振1H NMR图；
图2铜酞菁1的质谱图；
图3铜酞菁1 紫外谱图分析；
图4 3-(对叔丁基苯氧基）邻苯二腈配体核磁共振1H NMR图；
图5铜酞菁2的质谱谱图；
图6铜酞菁2的紫外谱图。
具体实施方式
下面结合实施例对本发明进行详细说明。
1.具有催化作用的新型铜酞菁金属有机配合物的制备方法和反应条件
a)两种配体的的制备
配体一 量取30ml的DMF加入到150ml的反应瓶中，冰水浴，保持温度3℃以下。氩气保护下，称取NaH加入到DMF中，搅拌10min。称取2,4-二甲基-3-戊醇滴加到上述溶液中，搅拌1.5h。称取3-硝基邻苯二腈溶于10ml DMF后，滴加入上述反应液中，反应1h，移除冰水浴。静置片刻，倒入500ml水，有大量棕色固体析出。减压抽滤，水洗三次。将所得固体溶于氯仿，以硫酸钠干燥。干燥后产品以氯仿为洗脱剂，柱层析法纯化。纯化得到的有色产品中加入石油醚，减压抽滤，用石油醚润洗除去杂色，干燥，称重。
配体二 在150 mL反应瓶内称取3-硝基邻苯二腈、对叔丁基苯酚、 K2CO3，及20mlDMSO混合反应。溶液颜色由橘黄色渐变为橘红色。反应结束过滤，产品加入DMSO，磁力搅拌1h，抽滤，依次用水、氯仿洗涤，以硫酸钠干燥。干燥后产品以氯仿为洗脱剂，柱层析法纯化。干燥，称重。
b）铜酞菁的合成
铜酞菁1 在氩气氛下，150 mL反应瓶中，依次按比例加入3-（2,4-二甲基-3-戊氧基）邻苯二腈、尿素、钼酸铵、氯化亚铜，硝基苯，160℃搅拌反应。反应初始为淡黄色溶液，160℃后，有墨绿色粘稠状物质生成，溶液变为棕色，2.5hr后溶液颜色棕变墨绿，且颜色不再改变。反应结束后，减压蒸馏，以正己烷、氯仿为洗脱剂，用柱层析法纯化，干燥，称重。
铜酞菁2 在150mL反应瓶中依次加入3-(对叔丁基苯氧基）邻苯二腈配体、尿素、钼酸铵、氯化亚铜、硝基苯为溶剂，165℃反应。反应初始溶液为黄色溶液，165℃后，溶液依次变为橘黄色、棕色、黑色，蓝黑色后，颜色不再发生改变。反应结束后，减压蒸馏。所得固体以氯仿为洗脱剂，柱层析法提纯，干燥，称重。
c) 新型铜酞菁金属配合物催化反应研究
通过优化温度、溶剂、催化剂用量等参数，对所合成的两种新型铜酞菁配合物催化碳氮偶联反应进行了活性测试。结果表明，两种配合物均有很好的催化活性。
两种新型铜酞菁金属有机配合物在碳氮偶联催化反应中均表现出，催化活性高，反应条件温和，溶剂无需处理即可使用，简单易行，后处理简单，且催化剂本身性质稳定，是一类有应用价值的催化剂。
图1 配体3-（2,4-二甲基-3-戊氧基）邻苯二腈的核磁共振1H NMR
1H NMR (CDCl3, 500 MHz): 0.95 (d, 6H), 1.01 (d, 6H), 2.13 (m, 2H), 4.05(t, 1H), 7.26 (d, 1H), 7.28(d, 1H), 7.57 (t, 1H).
图2 铜酞菁1的质谱图。
MS：m/z，1031.4，[M + H]+ (calcd for C60H72CuN8O4: 1031.5).
图3 铜酞菁1 紫外谱图分析。
图4 3-(对叔丁基苯氧基）邻苯二腈配体核磁共振1H NMR。
1H NMR (500 MHz, CDCl3): δ = 1.37 (s, 9 H, tert-Bu), 7.05 (d, 2H,tert-BuAr), 7.12 (d, 1H, Ar), 7.47 (m, 3H, Ar and tert-BuAr), 7.57 (t, 1H,Ar).
图5铜酞菁2的质谱谱图。
MS：m/z，1168.3，[M +H]+ (calcd for C72H65CuN8O4: 1168.5).
图6铜酞菁2的紫外谱图。

Claims (2)

1.两种铜钛菁金属有机配合物，其特征在于：两种配合物均以具有不同空间效应的配体与铜化合物反应，得到铜酞菁；通过在酞菁骨架上引入具有较大空间位阻的取代基，使酞菁分子间的π-π相互作用减弱，阻碍分子之间的聚集，改善铜酞菁的溶解性能；两种铜钛菁配合物结构如下所示：
。
2.两种铜钛菁金属有机配合物的制备方法，其特征在于，所述方法包括以下制备步骤：
a) 配体3-（2,4-二甲基-3-戊氧基）邻苯二腈的合成
量取30ml的DMF加入到150ml的反应瓶中，冰水浴，保持温度3℃以下；氩气保护下，称取NaH加入到DMF中，搅拌10min；称取2,4-二甲基-3-戊醇滴加到上述溶液中，搅拌1.5h；称取3-硝基邻苯二腈溶于10ml DMF后，滴加入上述反应液中，反应1h，移除冰水浴；静置片刻，倒入500ml水，有大量棕色固体析出；减压抽滤，水洗三次；将所得固体溶于氯仿，以硫酸钠干燥；干燥后产品以氯仿为洗脱剂，柱层析法纯化；纯化得到的有色产品中加入石油醚，减压抽滤，用石油醚润洗除去杂色，干燥，称重；
b) 铜酞菁1的合成
在氩气氛下，150 mL反应瓶中，依次按比例加入3-（2,4-二甲基-3-戊氧基）邻苯二腈、尿素、钼酸铵、氯化亚铜，硝基苯，160℃搅拌反应；反应初始为淡黄色溶液，160℃后，有墨绿色粘稠状物质生成，溶液变为棕色，2.5hr后溶液颜色变墨绿，且颜色不再改变；反应结束后，减压蒸馏，以正己烷、氯仿为洗脱剂，柱层析法纯化，干燥，称重；
c) 3-(对叔丁基苯氧基）邻苯二腈配体的合成
在150 mL反应瓶内称取3-硝基邻苯二腈、对叔丁基苯酚、 K2CO3，及20ml DMSO混合反应；溶液颜色由橘黄色渐变为橘红色；反应结束过滤，产品加入DMSO，磁力搅拌1h，抽滤，依次用水、氯仿洗涤，以硫酸钠干燥；干燥后产品以氯仿为洗脱剂，柱层析法纯化；干燥，称重；
d)铜酞菁2的合成
在150mL反应瓶中依次加入3-(对叔丁基苯氧基）邻苯二腈配体、尿素、钼酸铵、氯化亚铜、硝基苯为溶剂，165℃反应；反应初始溶液为黄色溶液，165℃后，溶液依次变为橘黄色、棕色、黑色，蓝黑色后，颜色不再发生改变；反应结束后，减压蒸馏；所得固体以氯仿为洗脱剂，柱层析法提纯，干燥，称重；
e)铜钛菁的催化性能测试
在氩气保护下，以卤化物、氮杂环化合物为底物，DMSO为溶剂，加入KOH，2％mmol的催化剂，反应2.5h，用水:乙酸乙酯=3:10萃取，无水Na2SO4干燥.以乙酸乙酯、石油醚为洗脱剂，柱层析法纯化得目标产物；
。
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