Solvent-Dependent Structural Variation of Zinc(II) Coordination Polymers and Their Catalytic Activity in the Knoevenagel Condensation Reaction

被引:96
作者
Karmakar, Anirban [1 ]
Rubio, Guilherme M. D. M. [1 ]
Guedes da Silva, M. Fatima C. [1 ]
Hazra, Susanta [1 ]
Pombeiro, Armando J. L. [1 ]
机构
[1] Univ Lisbon, Inst Super Tecn, Ctr Quim Estrutural, P-1049001 Lisbon, Portugal
基金
俄罗斯科学基金会;
关键词
METAL-ORGANIC FRAMEWORKS; DIASTEREOSELECTIVE HENRY REACTION; MILD PEROXIDATIVE OXIDATION; SECONDARY BUILDING UNITS; SUPRAMOLECULAR ISOMERISM; HYDROGEN STORAGE; HETEROGENEOUS CATALYSIS; DRUG-DELIVERY; IONIC LIQUID; LIGAND;
D O I
10.1021/acs.cgd.5b00948
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The novel self-assembled zinc(II) coordination polymers [Zn(L)(H2O)(2)](n) (1), [Zn(L)(H2O)(2)](n)center dot n(formamide) (2), [Zn(L)(H2O)(2)](n)center dot n(N-methylformamide) (3), [Zn(L)(H2O)(formamide)](n) (4), and [Zn-3(L)(2)-(formate)(2)(4,4'-bipyridine)(3)]center dot 2n(DMF)center dot 2n(H2O) (5) (L = 5-acetamidoi- sophthalate) have been synthesized and characterized by elemental micro-analysis, infrared spectroscopy, thermogravimetric analysis, and X-ray single crystal X-ray diffraction. 1, 2, and 3 are one-dimensional (1D) coordination polymers that crystallize in monoclinic P2(1), monoclinic P2(1)/m, and triclinic P1 systems, respectively, and are pseudo-polymorphic supramolecular isomers with 1 having a helical arrangement, and 2 and 3 exhibiting zigzag type structures containing different guest molecules. Compound 4 crystallizes in the triclinic P1 space group and is a 1D coordination polymer that exhibits fused 8-membered and 16-membered dimetallic rings. Compound 5 features a two-dimensional network type polymer with trimetallic cores. Compounds 1-5 expand to three-dimensional by means of H-bond interactions. These coordination polymers act as effective heterogeneous catalysts, under mild conditions, for the Knoevenagel condensation reaction of different aldehydes with an active methylene compound (malononitrile) and can be recycled without losing activity.
引用
收藏
页码:4185 / 4197
页数:13
相关论文
共 104 条
[81]   QUADRIATIC ELONGATION - QUANTITATIVE MEASURE OF DISTORTION IN COORDINATION POLYHEDRA [J].
ROBINSON, K ;
GIBBS, GV ;
RIBBE, PH .
SCIENCE, 1971, 172 (3983) :567-&
[82]   Hydrogen storage in microporous metal-organic frameworks [J].
Rosi, NL ;
Eckert, J ;
Eddaoudi, M ;
Vodak, DT ;
Kim, J ;
O'Keeffe, M ;
Yaghi, OM .
SCIENCE, 2003, 300 (5622) :1127-1129
[83]   Strategies for hydrogen storage in metal-organic frameworks [J].
Rowsell, JLC ;
Yaghi, OM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (30) :4670-4679
[84]   Knoevenagel condensation over β and Y zeolites in liquid phase under solvent free conditions [J].
Saravanamurugan, S ;
Palanichamy, M ;
Hartmann, M ;
Murugesan, V .
APPLIED CATALYSIS A-GENERAL, 2006, 298 :8-15
[85]  
Schroder M., 2004, ENCY SUPRAMOLECULAR, V2, P1420
[86]   A homochiral metal-organic porous material for enantioselective separation and catalysis [J].
Seo, JS ;
Whang, D ;
Lee, H ;
Jun, SI ;
Oh, J ;
Jeon, YJ ;
Kim, K .
NATURE, 2000, 404 (6781) :982-986
[87]   Two-dimensional rhombus grid coordination polymer showing heterogeneous catalytic activities [J].
Sharma, Manish K. ;
Singh, Prabal P. ;
Bharadwaj, Parimal K. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2011, 342-43 :6-10
[88]   A short history of SHELX [J].
Sheldrick, George M. .
ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2008, 64 :112-122
[89]   Potassium fluoride doped fluorapatite and hydroxyapatite as new catalysts in organic synthesis [J].
Smahi, A ;
Solhy, A ;
El Badaoui, H ;
Amoukal, A ;
Tikad, A ;
Maizi, M ;
Sebti, S .
APPLIED CATALYSIS A-GENERAL, 2003, 250 (01) :151-159
[90]   α- and β-bis(1,1,1-trifluoro-5,5-dimethyl-5-methoxyacetylacetonato)copper(II):: Transforming the dense polymorph into a versatile new microporous framework [J].
Soldatov, DV ;
Ripmeester, JA ;
Shergina, SI ;
Sokolov, IE ;
Zanina, AS ;
Gromilov, SA ;
Dyadin, YA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4179-4188