CN105399758A - 一种环状手性配位聚合物及其制备方法与应用 - Google Patents
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- 229920000642 polymer Polymers 0.000 claims description 38
- 125000004122 cyclic group Chemical group 0.000 claims description 24
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 claims description 12
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- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000013110 organic ligand Substances 0.000 claims description 3
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- 238000005516 engineering process Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
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- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract 1
- 238000006842 Henry reaction Methods 0.000 abstract 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 abstract 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
- B01J31/182—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine comprising aliphatic or saturated rings
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- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
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Abstract
本发明公开了一种环状手性配位聚合物及其制备方法与应用，其化学式为[Cu3(R,R-cdpa)3(CH3OH)3].6ClO4.3CH3OH，制备方法包括将Cu(ClO4)2·6H2O和R,R-cdpa加入8mL？CH3OH溶液中进行混合，得到悬浊液；将该悬浮液转移到反应釜中反应后制得环状手性配位聚合物。优点为本发明采用基于手性环己二胺的双螯合配体R,R-cdpa与Cu(II)构筑了一种环状手性配位聚合物；同时，本发明的制备工艺简单，无需复杂的合成设备，降低生产成本；此外，制备的配位聚合物能够应用于芳香醛与硝基甲烷的不对称亨利反应。
Description
技术领域
本发明属于化学领域，尤其涉及一种环状手性配位聚合物及其制备方法与应用。
背景技术
手性配合物的设计和合成是配位化学的热点领域之一，这是因为它们的结构富于变化，能表现出丰富多彩的拓扑结构，因此不仅具有结构的理论研究意义，同时可作为优良的功能材料，具有诱人的应用前景。目前对于这种材料的研究主要集中于不对称催化、对映体选择分离、二阶非线性光学材料和铁电材料等。近年来，国内外很多课题组在手性配合物的不对称催化方面做出了大量卓有成效的工作，但主要集中在较高维数(二维和三维)的配位聚合物，特别是具有孔道结构的金属-有机骨架材料。同时，环状手性配位聚合物作为一种有趣的手性化合物，在不对称催化方面也应该具有潜在的应用价值，但文献中还没有这方面的研究报道。此外，文献中已有手性环己二胺和Cu(II)盐的加合物应用在不对称亨利反应方面的报道。
发明内容
发明目的：本发明的第一目的是提供一种一维的且具有环状的手性配位聚合物；本发明的第二目的是提供该配位聚合物的制备方法；本发明的第三目的是提供该配位聚合物的应用。
技术方案：本发明的环状手性配位聚合物的化学式为[Cu3(R,R-cdpa)3(CH3OH)3].6ClO4.3CH3OH，其中，R,R-cdpa为，其为手性双螯合有机配体。进一步说，该配位聚合物具有三个Cu(II)和三个R,R-cdpa形成的3加3环状结构，其属于单斜晶系，空间群为P21，结晶参数为 β＝99.128(3)°，其中，a，b，c分别为晶胞的三条棱的棱长，β为a棱和c棱的夹角。
更进一步说，本发明的R,R-cdpa配体采用反式双螯合模式与两个Cu(II)配位，而Cu(II)为五配位的四方锥结构，四方锥的底部平面被两个螯合配体的两个氮原子和两个氧原子占据，四方锥的顶点位置被一个水分子占据，四方锥底部配位的四个原子不在同一个平面上，其中，R,R-cdpa配体的结构式为：
本发明的环状手性配位聚合物的制备方法包括如下步骤：
(1)将0.1mmol的Cu(ClO4)2·6H2O和0.1mmol的R,R-cdpa加入8mLCH3OH溶液中进行混合，室温下搅拌20min，得到悬浊液；
(2)将上述悬浮液转移到15mL内衬聚四氟乙烯的反应釜中加热90℃反应3天后，以5℃/h的速率缓慢降至室温、过滤、静置后制得环状手性配位聚合物。
本发明的环状手性配位聚合物应用于芳香醛与硝基甲烷的不对称亨利反应。
有益效果：与现有技术相比，其显著优点为本发明采用基于手性环己二胺的双螯合配体R,R-cdpa与Cu(II)构筑了一种环状手性配位聚合物；同时，本发明的制备工艺简单，无需复杂的合成设备，降低生产成本；此外，制备的配位聚合物能够应用于芳香醛与硝基甲烷的不对称亨利反应，从而为手性螺旋配合物作为多相催化剂在不对称催化中的应用提供了原创性探索和可行性研究。
附图说明
图1为本发明制得的配位聚合物的分子结构图。
具体实施方式
本发明的环状手性配位聚合物的化学式为[Cu3(R,R-cdpa)3(CH3OH)3].6ClO4.3CH3OH，其中，R,R-cdpa为(-)-N,N'-(1R,2R)-1,2-二氨基环己胺二基双(2-吡啶酰苯胺)，其为手性双螯合有机配体。进一步说，该配位聚合物具有三个Cu(II)和三个R,R-cdpa形成的3加3环状结构，其属于单斜晶系，空间群为P21，结晶参数为 β＝99.128(3)°，其中，a，b，c分别为晶胞的三条棱的棱长，β为a棱和c棱的夹角。
更进一步说，本发明的R,R-cdpa配体采用反式双螯合模式与两个Cu(II)配位，而Cu(II)为五配位的四方锥结构，四方锥的底部平面被两个螯合配体的两个氮原子和两个氧原子占据，四方锥的顶点位置被一个水分子占据，四方锥底部配位的四个原子不在同一个平面上，其中，R,R-cdpa配体的结构式为：
本发明的环状手性配位聚合物的制备方法包括如下步骤：
(1)将0.1mmol的Cu(ClO4)2·6H2O和0.1mmol的R,R-cdpa加入8mLCH3OH溶液中进行混合，室温下搅拌20min，得到悬浊液；
(2)将上述悬浮液转移到15mL内衬聚四氟乙烯的反应釜中加热90℃反应3天后，以5℃/h的速率缓慢降至室温、过滤、静置后制得环状手性配位聚合物。
本发明的环状手性配位聚合物应用于芳香醛与硝基甲烷的不对称亨利反应。进一步说，芳香醛为1-萘甲醛和单取代苯甲醛(取代基为H，2-/3-/4-NO2，2-/3-/4-F，2-/4-Cl，2-/3-/4-Br，4-OCH3或4-Ph)。
实施例1
将0.1mmol的Cu(ClO4)2·6H2O和0.1mmol的R,R-cdpa加入8mLCH3OH溶液中进行混合，室温下搅拌20min，得到悬浊液；将上述悬浮液转移到15mL内衬聚四氟乙烯的反应釜中加热90℃反应3天后，以5℃/h的速率缓慢降至室温、过滤、静置后制得环状手性配位聚合物，将该配位聚合物经过单晶X-射线衍射分析得到的分子结构图如图1所示。
实施例2
将0.1mmol的Cu(ClO4)2·6H2O和0.1mmol的R,R-cdpa加入8mLCH3OH溶液中进行混合，室温下搅拌20min，得到悬浊液；将上述悬浮液转移到15mL内衬聚四氟乙烯的反应釜中加热90℃反应3天后，以5℃/h的速率缓慢降至室温、过滤、静置后制得环状手性配位聚合物。
实施例3
向4mL的小试管中加入0.5mmol配位聚合物，1mL异丙醇(i-PrOH)和5mmolN,N-二异丙基乙胺(DIPEA)得到一蓝色悬浮液，然后向悬浮液中加入0.5mmol的芳香醛和5mmol的硝基甲烷，将试管放入低温反应器中，在-20℃条件下反应168h后过滤，将滤液过柱纯化，其中，填充剂为硅胶，流动相为体积比4:1的石油醚和乙酸乙酯混合溶剂，将所得溶液浓缩、真空干燥后，即得到催化产物，其催化反应方程式如下式所示。
将所得的催化产物用带有手性柱的高效液相色谱测定e.e.值。其中，所用手性柱和液相条件，以及所得产物的e.e.值如表1所示。
表1催化产物的e.e.值
由表1可知，该手性螺旋配合物作为主催化剂的情况下，芳香醛和硝基甲烷的不对称亨利反应可以得到较好的不对称催化效果；其有可能应用到工业反应中。
Claims (9)
1.一种环状手性配位聚合物，其特征在于：该配位聚合物的化学式为[Cu3(R,R-cdpa)3(CH3OH)3].6ClO4.3CH3OH，其中，R,R-cdpa为，其为手性双螯合有机配体。
2.根据权利要求1所述的环状手性配位聚合物，其特征在于：所述配位聚合物具有三个Cu(II)和三个R,R-cdpa形成的3加3环状结构。
3.根据权利要求1所述的环状手性配位聚合物，其特征在于：所述配位聚合物属于单斜晶系，空间群为P21。
4.根据权利要求1所述的环状手性配位聚合物，其特征在于：所述配位聚合物的结晶参数为β＝99.128(3)°，其中，a，b，c分别为晶胞的三条棱的棱长，β为a棱和c棱的夹角。
5.根据权利要求1所述的环状手性配位聚合物，其特征在于：所述的R,R-cdpa配体的结构式为：
6.根据权利要求5所述的环状手性配位聚合物，其特征在于：所述R,R-cdpa配体采用反式双螯合模式与两个Cu(II)配位。
7.根据权利要求6所述的环状手性配位聚合物，其特征在于：所述Cu(II)为五配位的四方锥结构，四方锥的底部平面被两个螯合配体的两个氮原子和两个氧原子占据，四方锥的顶点位置被一个水分子占据，四方锥底部配位的四个原子不在同一个平面上。
8.一种制备权利要求1所述的环状手性配位聚合物的方法，其特征在于包括如下步骤：
(1)将0.1mmol的Cu(ClO4)2·6H2O和0.1mmol的R,R-cdpa加入8mLCH3OH溶液中进行混合，室温下搅拌20min，得到悬浊液；
(2)将上述悬浮液转移到15mL内衬聚四氟乙烯的反应釜中加热90℃反应3天后，以5℃/h的速率缓慢降至室温、过滤、静置后制得环状手性配位聚合物。
9.一种权利要求1所述的环状手性配位聚合物应用于芳香醛与硝基甲烷的不对称亨利反应。
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Cited By (2)
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|---|---|---|---|---|
| CN109503737A (zh) * | 2018-11-19 | 2019-03-22 | 石家庄学院 | 一种聚苯乙烯固载的手性二胺类配体及其制备方法和应用 |
| CN110560173A (zh) * | 2019-09-17 | 2019-12-13 | 哈尔滨工业大学 | 双吡啶酰胺铁负载纳米二氧化硅异相催化剂的制备方法和应用方法 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503737A (zh) * | 2018-11-19 | 2019-03-22 | 石家庄学院 | 一种聚苯乙烯固载的手性二胺类配体及其制备方法和应用 |
| CN109503737B (zh) * | 2018-11-19 | 2021-03-05 | 石家庄学院 | 一种聚苯乙烯固载的手性二胺类配体及其制备方法和应用 |
| CN110560173A (zh) * | 2019-09-17 | 2019-12-13 | 哈尔滨工业大学 | 双吡啶酰胺铁负载纳米二氧化硅异相催化剂的制备方法和应用方法 |
| CN110560173B (zh) * | 2019-09-17 | 2022-03-04 | 哈尔滨工业大学 | 双吡啶酰胺铁负载纳米二氧化硅异相催化剂的制备方法和应用方法 |
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