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Journal articles on the topic 'Chiral metal salen complexes'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Gualandi, Andrea, Francesco Calogero, Simone Potenti, and Pier Giorgio Cozzi. "Al(Salen) Metal Complexes in Stereoselective Catalysis." Molecules 24, no. 9 (May 2, 2019): 1716. http://dx.doi.org/10.3390/molecules24091716.

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Salen ligands are a class of Schiff bases simply obtained through condensation of two molecules of a hydroxyl-substituted aryl aldehyde with an achiral or chiral diamine. The prototype salen, or N,N′-bis(salicylidene)ethylenediamine has a long history, as it was first reported in 1889, and immediately, some of its metal complexes were also described. Now, the salen ligands are a class of N,N,O,O tetradentate Schiff bases capable of coordinating many metal ions. The geometry and the stereogenic group inserted in the diamine backbone or aryl aldehyde backbone have been utilized in the past to efficiently transmit chiral information in a variety of different reactions. In this review we will summarize the important and recent achievements obtained in stereocontrolled reactions in which Al(salen) metal complexes are employed. Several other reviews devoted to the general applications and synthesis of chromium and other metal salens have already been published.

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2

K. Shiryaev, Andrey. "Recent Advances in Chiral Catalysis Using Metal Salen Complexes." Current Organic Chemistry 16, no. 15 (July 1, 2012): 1788–807. http://dx.doi.org/10.2174/138527212802651340.

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3

Shaw, Subrata, and James D. White. "Asymmetric Catalysis Using Chiral Salen–Metal Complexes: Recent Advances." Chemical Reviews 119, no. 16 (June 11, 2019): 9381–426. http://dx.doi.org/10.1021/acs.chemrev.9b00074.

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4

O'Connor, Kenneth J., Shiow-Jyi Wey, and Cynthia J. Burrows. "Alkene aziridination and epoxidation catalyzed by chiral metal salen complexes." Tetrahedron Letters 33, no. 8 (February 1992): 1001–4. http://dx.doi.org/10.1016/s0040-4039(00)91844-6.

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5

Belokon, Yuri N., Michael North, Vadim S. Kublitski, Nikolai S. Ikonnikov, Pavel E. Krasik, and Viktor I. Maleev. "Chiral salen-metal complexes as novel catalysts for asymmetric phase transfer alkylations." Tetrahedron Letters 40, no. 33 (August 1999): 6105–8. http://dx.doi.org/10.1016/s0040-4039(99)01214-9.

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6

Canali, Laetitia, and David C. Sherrington. "Utilisation of homogeneous and supported chiral metal(salen) complexes in asymmetric catalysis." Chemical Society Reviews 28, no. 2 (1999): 85–93. http://dx.doi.org/10.1039/a806483k.

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7

O'CONNOR, K. J., S. J. WEY, and C. J. BURROWS. "ChemInform Abstract: Alkene Aziridination and Epoxidation Catalyzed by Chiral Metal Salen Complexes." ChemInform 23, no. 37 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199237060.

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8

Liu, Tao, Wen-Juan Ruan, Jing Nan, and Zhi-Ang Zhu. "CD Spectroscopic Study on the Molecular Recognition of Chiral Salen-Metal Complexes." Chinese Journal of Chemistry 21, no. 7 (August 26, 2010): 751–55. http://dx.doi.org/10.1002/cjoc.20030210709.

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9

Patti, Angela, Sonia Pedotti, Francesco Ballistreri, and Giuseppe Sfrazzetto. "Synthesis and Characterization of Some Chiral Metal-Salen Complexes Bearing a Ferrocenophane Substituent." Molecules 14, no. 11 (October 26, 2009): 4312–25. http://dx.doi.org/10.3390/molecules14114312.

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10

Canali, Laetitia, and David C. Sherrington. "ChemInform Abstract: Utilization of Homogeneous and Supported Chiral Metal(salen) Complexes in Asymmetric Catalysis." ChemInform 30, no. 21 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199921284.

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11

Belokon, Yuri N., Michael North, Vadim S. Kublitski, Nikolai S. Ikonnikov, Pavel E. Krasik, and Viktor I. Maleev. "ChemInform Abstract: Chiral Salen-Metal Complexes as Novel Catalysts for Asymmetric Phase-Transfer Alkylations." ChemInform 30, no. 45 (June 12, 2010): no. http://dx.doi.org/10.1002/chin.199945044.

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12

Akine, Shigehisa. "Dynamic Helicity Control of Oligo(salamo)-Based Metal Helicates." Inorganics 6, no. 3 (August 17, 2018): 80. http://dx.doi.org/10.3390/inorganics6030080.

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Much attention has recently focused on helical structures that can change their helicity in response to external stimuli. The requirements for the invertible helical structures are a dynamic feature and well-defined structures. In this context, helical metal complexes with a labile coordination sphere have a great advantage. There are several types of dynamic helicity controls, including the responsive helicity inversion. In this review article, dynamic helical structures based on oligo(salamo) metal complexes are described as one of the possible designs. The introduction of chiral carboxylate ions into Zn3La tetranuclear structures as an additive is effective to control the P/M ratio of the helix. The dynamic helicity inversion can be achieved by chemical modification, such as protonation/deprotonation or desilylation with fluoride ion. When (S)-2-hydroxypropyl groups are introduced into the oligo(salamo) ligand, the helicity of the resultant complexes is sensitively influenced by the metal ions. The replacement of the metal ions based on the affinity trend resulted in a sequential multistep helicity inversion. Chiral salen derivatives are also effective to bias the helicity; by incorporating the gauche/anti transformation of a 1,2-disubstituted ethylene unit, a fully predictable helicity inversion system was achieved, in which the helicity can be controlled by the molecular lengths of the diammonium guests.

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13

Delahaye, Émilie, Mayoro Diop, Richard Welter, Mauro Boero, Carlo Massobrio, Pierre Rabu, and Guillaume Rogez. "From Salicylaldehyde to Chiral Salen Sulfonates - Syntheses, Structures and Properties of New Transition Metal Complexes Derived from Sulfonato Salen Ligands." European Journal of Inorganic Chemistry 2010, no. 28 (July 27, 2010): 4450–61. http://dx.doi.org/10.1002/ejic.201000487.

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14

Sunaga, Nobumitsu, Tomoyuki Haraguchi, and Takashiro Akitsu. "Orientation of Chiral Schiff Base Metal Complexes Involving Azo-Groups for Induced CD on Gold Nanoparticles by Polarized UV Light Irradiation." Symmetry 11, no. 9 (September 2, 2019): 1094. http://dx.doi.org/10.3390/sym11091094.

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In this study, we report the synthesis, characterization, and chiroptical properties of azo-group-containing chiral salen type Schiff base Ni(II), Cu(II), and Zn(II) complexes absorbed on gold nanoparticles (AuNPs) of 10 nm diameters. Induced circular dichroism (CD) around the plasmon region from the chiral species weakly adsorbed on the surface of AuNP were observed when there were appropriate dipole–dipole interactions at the initial states. Spectral changes were also observed by not only cis-trans photoisomerization of azo-groups but also changes of orientation due to Weigert effect of azo-dyes after linearly polarized UV light irradiation. Spatial features were discussed based on dipole-dipole interactions mainly within an exciton framework.

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15

Tak, Raj Kumar, Manish Kumar, Mohd Nazish, Tushar Kumar Menapara, Rukhsana I. Kureshy, and Noor-ul H. Khan. "Development of recyclable chiral macrocyclic metal complexes for asymmetric aminolysis of epoxides: application for the synthesis of an enantiopure oxazolidine ring." New Journal of Chemistry 42, no. 18 (2018): 15325–31. http://dx.doi.org/10.1039/c8nj02960a.

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Macrocyclic Cr(iii)-salen complexes were synthesized for the ring opening reaction of various epoxides with anilines to furnish the corresponding β-amino-α-hydroxyl esters and β-amino alcohols with excellent ee/yield upto 99/95%.

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16

Peng, Bin, Wen-Hui Zhou, Lin Yan, Han-Wen Liu, and Li Zhu. "DNA-binding and cleavage studies of chiral Mn(III) salen complexes." Transition Metal Chemistry 34, no. 2 (January 6, 2009): 231–37. http://dx.doi.org/10.1007/s11243-008-9183-7.

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17

Nielsen, Morten, Niels B. Larsen, and Kurt V. Gothelf. "Electron Transfer Reactions of Self-Assembled Monolayers of Thio(Phenylacetylene)n-Substituted Chiral Metal−Salen Complexes." Langmuir 18, no. 7 (April 2002): 2795–99. http://dx.doi.org/10.1021/la015715+.

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18

Colon, Marisabel Lebron, Steven Y. Qian, Donald Vanderveer, and Xiu R. Bu. "Chiral bimetallic complexes from chiral salen metal complexes and mercury (II) halides and acetates: the anionic groups interact with Cu(II) in apical position." Inorganica Chimica Acta 357, no. 1 (January 2004): 83–88. http://dx.doi.org/10.1016/s0020-1693(03)00426-2.

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19

Belokon, Yuri N., Michael North, Tatiana D. Churkina, Nikolai S. Ikonnikov, and Victor I. Maleev. "Chiral salen–metal complexes as novel catalysts for the asymmetric synthesis of α-amino acids under phase transfer catalysis conditions." Tetrahedron 57, no. 13 (March 2001): 2491–98. http://dx.doi.org/10.1016/s0040-4020(01)00072-2.

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20

Belokon, Yuri N., Michael North, Tatiana D. Churkina, Nikolai S. Ikonnikov, and Victor I. Maleev. "ChemInform Abstract: Chiral Salen-Metal Complexes as Novel Catalysts for the Asymmetric Synthesis of α-Amino Acids under Phase Transfer Catalysis Conditions." ChemInform 32, no. 30 (May 25, 2010): no. http://dx.doi.org/10.1002/chin.200130192.

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21

Rigamonti, Luca, Alessandra Forni, Elena Cariati, Gianluca Malavasi, and Alessandro Pasini. "Solid-State Nonlinear Optical Properties of Mononuclear Copper(II) Complexes with Chiral Tridentate and Tetradentate Schiff Base Ligands." Materials 12, no. 21 (November 1, 2019): 3595. http://dx.doi.org/10.3390/ma12213595.

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Salen-type metal complexes have been actively studied for their nonlinear optical (NLO) properties, and push-pull compounds with charge asymmetry generated by electron releasing and withdrawing groups have shown promising results. As a continuation of our research in this field and aiming at solid-state features, herein we report on the synthesis of mononuclear copper(II) derivatives bearing either tridentate N2O Schiff bases L(a−c)− and pyridine as the forth ancillary ligand, [Cu(La−c)(py)](ClO4) (1a–c), or unsymmetrically-substituted push-pull tetradentate N2O2 Schiff base ligands, [Cu(5-A-5′-D-saldpen/chxn)] (2a–c), both derived from 5-substituted salicylaldehydes (sal) and the diamines (1R,2R)-1,2-diphenylethanediamine (dpen) and (1S,2S)-1,2-diaminocyclohexane (chxn). All compounds were characterized through elemental analysis, infrared and UV/visible spectroscopies, and mass spectrometry in order to guarantee their purity and assess their charge transfer properties. The structures of 1a–c were determined via single-crystal X-ray diffraction studies. The geometries of cations of 1a–c and of molecules 2a–c were optimized through DFT calculations. The solid-state NLO behavior was measured by the Kurtz–Perry powder technique @1.907 µm. All chiral derivatives possess non-zero quadratic electric susceptibility (χ(2)) and an efficiency of about 0.15–0.45 times that of standard urea.

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22

Bolotov, P. M., V. N. Khrustalev, and V. I. Maleev. "New biionic transition metal complexes based on the salen ligands: synthesis and application as synthons in the preparation of chiral homo- and heterobimetallic systems." Russian Chemical Bulletin 60, no. 8 (August 2011): 1612–19. http://dx.doi.org/10.1007/s11172-011-0241-5.

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23

Zhang, Wen-Zhen, and Xiao-Bing Lu. "ChemInform Abstract: Chiral Salen Complexes." ChemInform 43, no. 1 (December 9, 2011): no. http://dx.doi.org/10.1002/chin.201201247.

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24

IRIE, Ryo. "Asymmetric Epoxidation Using Chiral Salen Complexes." Journal of Synthetic Organic Chemistry, Japan 51, no. 5 (1993): 412–20. http://dx.doi.org/10.5059/yukigoseikyokaishi.51.412.

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25

Cavazzini, Marco, Amedea Manfredi, Fernando Montanari, Silvio Quici, and Gianluca Pozzi. "Second-generation fluorous chiral (salen) manganese complexes." Chemical Communications, no. 21 (2000): 2171–72. http://dx.doi.org/10.1039/b007053j.

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26

Liu, Qiancai, Christian Meermann, Hans W. Görlitzer, Oliver Runte, Eberhardt Herdtweck, Peter Sirsch, Karl W. Törnroos, and Reiner Anwander. "Cationic rare-earth metal SALEN complexes." Dalton Transactions, no. 44 (2008): 6170. http://dx.doi.org/10.1039/b808781d.

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27

Achard, Thierry R. J., William Clegg, Ross W. Harrington, and Michael North. "Chiral salen ligands designed to form polymetallic complexes." Tetrahedron 68, no. 1 (January 2012): 133–44. http://dx.doi.org/10.1016/j.tet.2011.10.084.

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28

Mizuno, Toshihisa, Masayuki Takeuchi, and Seiji Shinkai. "Sugar sensing using chiral salen-Co(II) complexes." Tetrahedron 55, no. 31 (July 1999): 9455–68. http://dx.doi.org/10.1016/s0040-4020(99)00519-0.

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29

IRIE, R. "ChemInform Abstract: Asymmetric Epoxidation Using Chiral Salen Complexes." ChemInform 24, no. 42 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199342300.

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30

Koyama, Kyohei, Kodai Iijima, Dongho Yoo, and Takehiko Mori. "Transistor properties of salen-type metal complexes." RSC Advances 10, no. 49 (2020): 29603–9. http://dx.doi.org/10.1039/d0ra05449f.

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31

H. Ali, Safaa, Hassan M. A. Al-Redha, and Bassam A. Sachit. "Antibacterial activity of some Salen metal complexes." IOP Conference Series: Materials Science and Engineering 928 (November 19, 2020): 052016. http://dx.doi.org/10.1088/1757-899x/928/5/052016.

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32

Puglisi, Roberta, Francesco P. Ballistreri, Chiara M. A. Gangemi, Rosa Maria Toscano, Gaetano A. Tomaselli, Andrea Pappalardo, and Giuseppe Trusso Sfrazzetto. "Chiral Zn–salen complexes: a new class of fluorescent receptors for enantiodiscrimination of chiral amines." New Journal of Chemistry 41, no. 3 (2017): 911–15. http://dx.doi.org/10.1039/c6nj03592b.

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33

Ernst, S., E. Fuchs, and X. Yang. "Enantioselective hydrogenation on zeolite-encapsulated chiral palladium–salen complexes." Microporous and Mesoporous Materials 35-36 (April 2000): 137–42. http://dx.doi.org/10.1016/s1387-1811(99)00214-0.

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34

Voituriez, Arnaud, Mohamed Mellah, and Emmanuelle Schulz. "Design and electropolymerization of new chiral thiophene–salen complexes." Synthetic Metals 156, no. 2-4 (February 2006): 166–75. http://dx.doi.org/10.1016/j.synthmet.2005.11.004.

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35

Zulauf, Anaïs, Mohamed Mellah, Xiang Hong, and Emmanuelle Schulz. "Recoverable chiral salen complexes for asymmetric catalysis: recent progress." Dalton Transactions 39, no. 30 (2010): 6911. http://dx.doi.org/10.1039/c001943g.

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36

Cavazzini, Marco, Amedea Manfredi, Fernando Montanari, Silvio Quici, and Gianluca Pozzi. "ChemInform Abstract: Second-Generation Fluorous Chiral (Salen) Manganese Complexes." ChemInform 32, no. 5 (January 30, 2001): no. http://dx.doi.org/10.1002/chin.200105030.

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37

Schulz, Emmanuelle. "Chiral Cobalt‐Salen Complexes: Ubiquitous Species in Asymmetric Catalysis." Chemical Record 21, no. 2 (January 26, 2021): 427–39. http://dx.doi.org/10.1002/tcr.202000166.

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38

Song, Feijie, Teng Zhang, Cheng Wang, and Wenbin Lin. "Chiral porous metal-organic frameworks with dual active sites for sequential asymmetric catalysis." Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences 468, no. 2143 (March 14, 2012): 2035–52. http://dx.doi.org/10.1098/rspa.2012.0100.

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Metal-organic frameworks (MOFs) are a class of organic–inorganic hybrid materials built from metal-connecting nodes and organic-bridging ligands. They have received much attention in recent years owing to the ability to tune their properties for potential applications in various areas. Properly designed MOFs with uniform, periodically aligned active sites have shown great promise in catalysing shape-, size-, chemo-, regio- and stereo-selective organic transformations. This study reports the synthesis and characterization of two chiral MOFs (CMOFs 1 and 2 ) that are constructed from Mn-salen-derived dicarboxylic acids [salen is ( R , R )- N , N ′-bis(5- tert -butylsalicylidene)-1,2-cyclohexanediamine], bis(4-vinylbenzoic acid)-salen manganese(III) chloride (H 2 L 4 ) or bis(benzoic acid)-salen manganese(III) chloride (H 2 L 3 ) and [Zn 4 (μ 4 -O)(O 2 CR) 6 ] or [Zn 5 (H 2 O) 2 (μ 3 -OH) 2 (O 2 CR) 8 ] secondary building units (SBUs), respectively. The SBUs in CMOF- 1 are connected by the linear ditopic Mn-salen-derived linkers to construct a fourfold interpenetrated isoreticular MOF (IRMOF) structure with pcu topology. In CMOF- 2 , the Mn-salen centres dimerize in a cross-linking way to form a diamondoid structure with threefold interpenetration. CMOF- 1 was examined for highly regio- and stereo-selective tandem alkene epoxidation/epoxide ring-opening reactions by using the Mn-salen andZn 4 (μ 4 -O)(carboxylate) 6 active sites, respectively. Our work demonstrated the potential utility of chiral MOFs with multiple active sites in the efficient synthesis of complex molecules with excellent regio- and stereo-controls

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39

Pop, Flavia, and Narcis Avarvari. "Chiral metal-dithiolene complexes." Coordination Chemistry Reviews 346 (September 2017): 20–31. http://dx.doi.org/10.1016/j.ccr.2016.11.015.

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40

Savchuk, Mariia, Steven Vertueux, Thomas Cauchy, Matthieu Loumaigne, Francesco Zinna, Lorenzo Di Bari, Nicolas Zigon, and Narcis Avarvari. "Schiff-base [4]helicene Zn(ii) complexes as chiral emitters." Dalton Transactions 50, no. 30 (2021): 10533–39. http://dx.doi.org/10.1039/d1dt01752g.

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41

Leoni, Luca, and Antonella Dalla Cort. "The Supramolecular Attitude of Metal–Salophen and Metal–Salen Complexes." Inorganics 6, no. 2 (April 24, 2018): 42. http://dx.doi.org/10.3390/inorganics6020042.

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42

Mihan, Francesco Yafteh, Silvia Bartocci, Michele Bruschini, Paolo De Bernardin, Gianpiero Forte, Ilaria Giannicchi, and Antonella Dalla Cort. "Ion-Pair Recognition by Metal - Salophen and Metal - Salen Complexes." Australian Journal of Chemistry 65, no. 12 (2012): 1638. http://dx.doi.org/10.1071/ch12353.

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The development of heteroditopic receptor systems that can simultaneously bind cationic and anionic species is one of the most challenging research topics in supramolecular chemistry, attracting the attention of a large number of research groups worldwide. Such an interest is due especially to the fact that the overall receptor–ion-pair complex is neutral and this can be advantageous in many situations, such as salt solubilization and extraction, and membrane-transport applications. Receptors designed for ion-pair complexation are molecules comprising well-known anion-binding motifs and familiar cation-binding sites. An important family of compounds that can use metal Lewis-acidic centres for anion recognition and that can be easily derivatized to introduce an additional binding site for the cation is metal–salophen and metal–salen complexes. This short review shows that the high versatility of salen and salophen ligands and of the corresponding metal complexes allows, through simple modifications of the basic skeleton, the obtention of highly efficient receptors for ion pairs.

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43

Rusmore, Theo A., Michael J. Behlen, Alex John, Daniel T. Glatzhofer, and Kenneth M. Nicholas. "Oxidative kinetic resolution of P-chiral phosphines catalyzed by chiral (salen)dioxomolybdenum complexes." Molecular Catalysis 513 (August 2021): 111776. http://dx.doi.org/10.1016/j.mcat.2021.111776.

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44

Lima, L. F., M. L. Corraza, L. Cardozo-Filho, H. Márquez-Alvarez, and O. A. C. Antunes. "Oxidation of limonene catalyzed by Metal(Salen) complexes." Brazilian Journal of Chemical Engineering 23, no. 1 (March 2006): 83–92. http://dx.doi.org/10.1590/s0104-66322006000100009.

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45

Fatibello‐Filho, Orlando, Edward Ralph Dockal, Luiz Humberto Marcolino‐Junior, and Marcos F. S. Teixeira. "Electrochemical Modified Electrodes Based on Metal‐Salen Complexes." Analytical Letters 40, no. 10 (August 2007): 1825–52. http://dx.doi.org/10.1080/00032710701487122.

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46

Schnuriger, Megan, Eric Tague, and Mark M. Richter. "Electrogenerated chemiluminescence properties of bisalicylideneethylenediamino (salen) metal complexes." Inorganica Chimica Acta 379, no. 1 (December 2011): 158–62. http://dx.doi.org/10.1016/j.ica.2011.10.010.

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47

Clarke, Ryan M., Khrystyna Herasymchuk, and Tim Storr. "Electronic structure elucidation in oxidized metal–salen complexes." Coordination Chemistry Reviews 352 (December 2017): 67–82. http://dx.doi.org/10.1016/j.ccr.2017.08.019.

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48

Peukert, Stefan, and Eric N. Jacobsen. "Enantioselective Parallel Synthesis Using Polymer-Supported Chiral Co(salen) Complexes." Organic Letters 1, no. 8 (October 1999): 1245–48. http://dx.doi.org/10.1021/ol990920q.

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49

Jiang, Chong Wen, Chen Chen Zhao, and Ke Yuan Zhou. "Copolymerization of Carbon Dioxide and Propylene Oxide Catalyzed by Salen Complexes." Advanced Materials Research 734-737 (August 2013): 2159–62. http://dx.doi.org/10.4028/www.scientific.net/amr.734-737.2159.

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Three salen complexes N,N'-bis(salicylidene)-1,2-phenylenediamino MⅢ Cl were prepared and employed for the copolymerization of carbon dioxide with propylene oxide. FT-IR and UV-Vis spectra confirmed the characteristic of metal salen complexes obtained. The central metal atoms in the salen complexes have great influence on the copolymerization of carbon dioxide with propylene oxide. The result shows that chromium metal is more effective to synthesize PPC copolymer. The structure of the resulting PPC was characterized by IR 1H NMR and GPC. 86.3% carbonate content of the PPC was achieved with chromium salen complexes.

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50

Baleizão, Carlos, Bárbara Gigante, Fernando Ramôa Ribeiro, Belen Ferrer, Emilio Palomares, and Hermenegildo Garcia. "Photochemistry of chiral pentacoordinated Al salen complexes. Chiral recognition in the quenching of photogenerated tetracoordinated Al salen transient by alkenes." Photochem. Photobiol. Sci. 2, no. 4 (2003): 386–92. http://dx.doi.org/10.1039/b211248e.

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