氮杂环/羧酸/Schiff碱配合物的合成与结构表征
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摘要
羧酸及其衍生物是一类重要的有机化合物,在工业、农业、国防等方面有重要的应用,尤其是在配位化学领域中应用广泛；Schiff碱是一类非常重要的含C=N双键配体,可以与大多数的金属配位形成配合物,配体及其配合物广泛应用于医药、催化、材料等方面；配位化合物由于在光、电、磁、催化、气体吸附等领域具有诱人的应用前景,被认为是当前最有潜力的功能材料,再加上它们可调控的结构框架,已成为无机化学和材料化学领域的研究热点之一。本文围绕当前配位化合物领域研究的若干热点,设计、合成并解析了20个配合物的单晶结构,对部分配合物的催化性能进行了研究。
1吡啶-2，6-二甲酸二钾盐和氯化锌反应,得到配位聚合物{C14H6N2K2O8Zn·7.5H2O}n 1；吡啶-2,6-二甲酸二钠盐和氯化锌反应,得到二聚体{[C28H12N4Na4O16Zn2·17H2O]}·5H2O}2。由于平衡电荷的阳离子不同,两个配合物的结构有很大差异,分子内结晶水的数量也不相同。
2以2,4-二羟基嘧啶-5-羧酸(H2dpc)为配体、邻菲啰啉(phen)或2，2'-联吡啶(bpy)为辅助配体,分别与CuCl2·2H2O、Cu(ClO4)2、MnCl2·4H2O和Nd(NO3)3·6H2O反应,得到相应的配合物[Cu(dpc)(phen)·H2O][Cu(dpc)(phen)]·7H2O3、[Cu(dpc)(bpy)·H2O](ClO4) 4、[Mn(dpc)2(CH3OH)2]·CH3OH5和[Nd(dpc)2(phen)·3(H2O)]·4H2O6。在这四个配合物中,虽然H2dpc中含有二个羟基,但只有一个羟基参与配位。
3以4,8-二羟基喹啉-2-羧酸(H2dqc)为配体、邻菲啰啉(phen)为辅助配体与NiCl2·6H2O反应,得到配合物{[Ni2(dqc)2(phen)2][Ni(phen)3]}·15H2O7。结构研究表明,晶体7中包括有一个[Ni(phen)3]2+和一个{[Ni(phen)(dqc)]2}2-结构单元,而目三个Ni(Ⅱ)的配位模式均不一样的。以均苯三甲酸(H3trim)和CdCl2·1.5H2O为原料水热合成得到配聚物{[Cd3(trim)2·9H2O]·H2O}n8。在镉的配合物8中,均苯三甲酸的三羧基均参与配位,形成二维网格状结构配聚物。
4尝试用CuCl2·2H2O、对二(1，2，4-三氮唑甲基)苯(btx)及Na2MoO4进行水热合成,仅仅得到配聚物[Cu(btX)2Cl2]n9;用对二(1H-咪唑基甲基)苯(bix)代替btx,采取类似的条件,却得到[(bix)4(Mo8O26)2]10;用1,3-二(1H-苯并咪唑基)丙烷(dbip)代替btx并加入NaSiO3进行水热合成则得到一个结构新颖的含杂多酸的配合物[CU2(dpip)4(H2O)2(SiMo12O40)]11。空间位阻、分子间弱相互作用等因素可能是造成这种差异的原因。
5详细探讨了配合物3、4、7、9和11分别在以水为溶剂、过氧化氢为氧化剂的非均相绿色反应条件下催化氧化2,6-二叔丁基苯酚的反应催化活性。结果表明,当作为非均相催化剂时,聚合物的催化活性明显较作为均相催化剂时的活性好,含Cu(Ⅱ)中心金属离了的配合物催化活性要比含Ni(Ⅱ)中心金属离子的配合物好。
6以水杨醛为原料合成得到8种Schiff碱配体HL1～L8,HL1～L8与Zn11、Ni11反应得到9个单核配合物,结构解析表明,X-离子的改变不影响晶体的空间结构(X-=C1-、Br-or l-)。研究了反应条件、金属离子、阴离子、溶剂等因素对Schiff base配合物结构的影响,为进一步设计、合成新的Schiff base配合物理论基础及依据。
Carboxylic acid and its derivates are of very important organic compounds, which are wildly used in industry, agriculture, national defense and other fields; Schiff bases and their metal complexes are very important compounds because their core group C=N has chemical and biological significance; Hitherto, research work is being done by researchers in the world, who have synthesized and estimated a plenty of Schiff bases and their metal complexes, studied and exploited many uses, such as catalyst, antibacterial medicines, material etc; Due to their potential applications in the fields of light, electricity, magnetism, catalysis, gas adsorption, etc., together with their controllable structural frameworks, complexes are considered to be the most promising functional materials and exhibit attractive prospects, and they have become one of the hot research realms in inorganic chemistry and materials. Herein, based on the current research in the field of coordination chemistry, we designed and synthesized 20 complexes and the network topology types of some complexes were studied.
1 Elevent complexes (1-11) contained Cu(Ⅱ)、Ni(Ⅱ)、Mn(Ⅱ)、Nd(Ⅲ) and Cd(Ⅱ) ions are designed and synthesized in order to study the catalysis of coordination complexes. Single crystal X-ray diffraction shows that coordination polymer {C14H6N2K2O8Zn·7.5H2O}n 1 displays infinitely extended two-dimensional reticulation structure but {[C28H12N4Na4O16Zn2·17H2O]}·5H2O 2 exhibits discrete binuclear structure though they have the same ligand pyridine-2,6-dicarboxylic acid but K(Ⅰ) as ion in 1 and Na(l) in 2. Using 2,4-dihydroxypyrimidine-4-carboxylic acid as ligand, complex [Cu(dpc)(phen)·H2O][Cu(dpc)(phen)]·7H2O 3、[Cu(dpc)(bpy)·H2O](ClO4) 4、[Mn(dpc)2(CH3OH)2]·CH3OH 5 and [Nd(dpc)2(phen)·3(H2O)]·4H2O 6 were obtained; Using 4,8-dihydroxyquinoline-2-carboxylic acid as ligand, complex {[Ni2(dqc)2(phen)2][Ni(phen)3]}·15H2O 7 was obtaind; Using benzene-1,3,5-tricarboxylic acid as ligand, coordination polymer{[Cd3(trim)2·9H2O]·H2O}n8 was obtained; Using N-containing ligands. coordination polymer [Cu(btx)2Cl2]n9 and two heteropoly acid anion containing complexes [(bix)4(Mo8O26)2] and [Cu2(dpip)4(H20)2(SiMo12O40)] 11 were obtained. (H2dpc= 2.4-dihydroxypyrimidine-4-carboxylic; H2dqc= 4,8-dihydroxyquinoline-2-carboxylic acid:phen = phenanthroline; bpy= 2,2'-bipyridyl; btx= 1,4-bis(1,2,4-triazol-1-ylmethyl)benzene; H3trim= trimesic acid; bix=1,4-bis(1H-imidiazole-1-ylmethyl)benzene; and dpip= 1,3-di(1H-benzimidazol-1-yl)propane).
2 A comparison of homogeneous vs heterogeneous catalytic activity for the oxidative coupling of 2,6-di-tert-butylphenol(2,6-DBP) by the aforementioned complexes 3、4、7、9 and 11 is performed by using H2O2(30% mass) as anoxidant in aqueous medium at elevated temperature. The results indicate that the complexes as heterogeneous catalysts record the higher conversion. Moreover, the experiment results showed that the catalytic activities of these complexes containing Cu11 ion are higher than that compound containing Ni11 ion.
3 By the condensation of equimolar amounts of salicylaldehyde with N-substituted-1,2 or 1,3-diamine in methanol solution the Schiff base HL1～L8 were synthesized and separated. All these mononuclear crystals characterized by X-ray diffractometer showed that they have strong M-N bond and the existent of X- have no effect on the syngoney (X-= Cl-,Br-,orI-,).
4. These Schiff base complexes have same metal ions, anions and different Schiff base ligands, or different metal ions, anions and similar structures. The influences of metal ions, anions, solvents, et al. on structures are researched and some rules are observed.
1吡啶-2，6-二甲酸二钾盐和氯化锌反应,得到配位聚合物{C14H6N2K2O8Zn·7.5H2O}n 1；吡啶-2,6-二甲酸二钠盐和氯化锌反应,得到二聚体{[C28H12N4Na4O16Zn2·17H2O]}·5H2O}2。由于平衡电荷的阳离子不同,两个配合物的结构有很大差异,分子内结晶水的数量也不相同。
2以2,4-二羟基嘧啶-5-羧酸(H2dpc)为配体、邻菲啰啉(phen)或2，2'-联吡啶(bpy)为辅助配体,分别与CuCl2·2H2O、Cu(ClO4)2、MnCl2·4H2O和Nd(NO3)3·6H2O反应,得到相应的配合物[Cu(dpc)(phen)·H2O][Cu(dpc)(phen)]·7H2O3、[Cu(dpc)(bpy)·H2O](ClO4) 4、[Mn(dpc)2(CH3OH)2]·CH3OH5和[Nd(dpc)2(phen)·3(H2O)]·4H2O6。在这四个配合物中,虽然H2dpc中含有二个羟基,但只有一个羟基参与配位。
3以4,8-二羟基喹啉-2-羧酸(H2dqc)为配体、邻菲啰啉(phen)为辅助配体与NiCl2·6H2O反应,得到配合物{[Ni2(dqc)2(phen)2][Ni(phen)3]}·15H2O7。结构研究表明,晶体7中包括有一个[Ni(phen)3]2+和一个{[Ni(phen)(dqc)]2}2-结构单元,而目三个Ni(Ⅱ)的配位模式均不一样的。以均苯三甲酸(H3trim)和CdCl2·1.5H2O为原料水热合成得到配聚物{[Cd3(trim)2·9H2O]·H2O}n8。在镉的配合物8中,均苯三甲酸的三羧基均参与配位,形成二维网格状结构配聚物。
4尝试用CuCl2·2H2O、对二(1，2，4-三氮唑甲基)苯(btx)及Na2MoO4进行水热合成,仅仅得到配聚物[Cu(btX)2Cl2]n9;用对二(1H-咪唑基甲基)苯(bix)代替btx,采取类似的条件,却得到[(bix)4(Mo8O26)2]10;用1,3-二(1H-苯并咪唑基)丙烷(dbip)代替btx并加入NaSiO3进行水热合成则得到一个结构新颖的含杂多酸的配合物[CU2(dpip)4(H2O)2(SiMo12O40)]11。空间位阻、分子间弱相互作用等因素可能是造成这种差异的原因。
5详细探讨了配合物3、4、7、9和11分别在以水为溶剂、过氧化氢为氧化剂的非均相绿色反应条件下催化氧化2,6-二叔丁基苯酚的反应催化活性。结果表明,当作为非均相催化剂时,聚合物的催化活性明显较作为均相催化剂时的活性好,含Cu(Ⅱ)中心金属离了的配合物催化活性要比含Ni(Ⅱ)中心金属离子的配合物好。
6以水杨醛为原料合成得到8种Schiff碱配体HL1～L8,HL1～L8与Zn11、Ni11反应得到9个单核配合物,结构解析表明,X-离子的改变不影响晶体的空间结构(X-=C1-、Br-or l-)。研究了反应条件、金属离子、阴离子、溶剂等因素对Schiff base配合物结构的影响,为进一步设计、合成新的Schiff base配合物理论基础及依据。
Carboxylic acid and its derivates are of very important organic compounds, which are wildly used in industry, agriculture, national defense and other fields; Schiff bases and their metal complexes are very important compounds because their core group C=N has chemical and biological significance; Hitherto, research work is being done by researchers in the world, who have synthesized and estimated a plenty of Schiff bases and their metal complexes, studied and exploited many uses, such as catalyst, antibacterial medicines, material etc; Due to their potential applications in the fields of light, electricity, magnetism, catalysis, gas adsorption, etc., together with their controllable structural frameworks, complexes are considered to be the most promising functional materials and exhibit attractive prospects, and they have become one of the hot research realms in inorganic chemistry and materials. Herein, based on the current research in the field of coordination chemistry, we designed and synthesized 20 complexes and the network topology types of some complexes were studied.
1 Elevent complexes (1-11) contained Cu(Ⅱ)、Ni(Ⅱ)、Mn(Ⅱ)、Nd(Ⅲ) and Cd(Ⅱ) ions are designed and synthesized in order to study the catalysis of coordination complexes. Single crystal X-ray diffraction shows that coordination polymer {C14H6N2K2O8Zn·7.5H2O}n 1 displays infinitely extended two-dimensional reticulation structure but {[C28H12N4Na4O16Zn2·17H2O]}·5H2O 2 exhibits discrete binuclear structure though they have the same ligand pyridine-2,6-dicarboxylic acid but K(Ⅰ) as ion in 1 and Na(l) in 2. Using 2,4-dihydroxypyrimidine-4-carboxylic acid as ligand, complex [Cu(dpc)(phen)·H2O][Cu(dpc)(phen)]·7H2O 3、[Cu(dpc)(bpy)·H2O](ClO4) 4、[Mn(dpc)2(CH3OH)2]·CH3OH 5 and [Nd(dpc)2(phen)·3(H2O)]·4H2O 6 were obtained; Using 4,8-dihydroxyquinoline-2-carboxylic acid as ligand, complex {[Ni2(dqc)2(phen)2][Ni(phen)3]}·15H2O 7 was obtaind; Using benzene-1,3,5-tricarboxylic acid as ligand, coordination polymer{[Cd3(trim)2·9H2O]·H2O}n8 was obtained; Using N-containing ligands. coordination polymer [Cu(btx)2Cl2]n9 and two heteropoly acid anion containing complexes [(bix)4(Mo8O26)2] and [Cu2(dpip)4(H20)2(SiMo12O40)] 11 were obtained. (H2dpc= 2.4-dihydroxypyrimidine-4-carboxylic; H2dqc= 4,8-dihydroxyquinoline-2-carboxylic acid:phen = phenanthroline; bpy= 2,2'-bipyridyl; btx= 1,4-bis(1,2,4-triazol-1-ylmethyl)benzene; H3trim= trimesic acid; bix=1,4-bis(1H-imidiazole-1-ylmethyl)benzene; and dpip= 1,3-di(1H-benzimidazol-1-yl)propane).
2 A comparison of homogeneous vs heterogeneous catalytic activity for the oxidative coupling of 2,6-di-tert-butylphenol(2,6-DBP) by the aforementioned complexes 3、4、7、9 and 11 is performed by using H2O2(30% mass) as anoxidant in aqueous medium at elevated temperature. The results indicate that the complexes as heterogeneous catalysts record the higher conversion. Moreover, the experiment results showed that the catalytic activities of these complexes containing Cu11 ion are higher than that compound containing Ni11 ion.
3 By the condensation of equimolar amounts of salicylaldehyde with N-substituted-1,2 or 1,3-diamine in methanol solution the Schiff base HL1～L8 were synthesized and separated. All these mononuclear crystals characterized by X-ray diffractometer showed that they have strong M-N bond and the existent of X- have no effect on the syngoney (X-= Cl-,Br-,orI-,).
4. These Schiff base complexes have same metal ions, anions and different Schiff base ligands, or different metal ions, anions and similar structures. The influences of metal ions, anions, solvents, et al. on structures are researched and some rules are observed.
引文
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