Syntheses, crystal structures, and characterization of four homochiral coordination polymers based on two chiral reduced Schiff base ligands

Ying, Shao‐Ming; Xiao-hui, Huang

doi:10.1007/s11243-013-9706-8

Cited by 4 publications

(3 citation statements)

References 26 publications

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“…By the reaction between the amine group of an l-amino acid and an aldehyde group, we introduced the chiral C atom of the l-amino acid to the Schiff base ligand, and then reduced the C N group to a C-N group in order to enhance the stability of the ligands. We have synthesized several reduced Schiff base compounds based on 4-carboxybenzaldehyde (Ying, 2012;Ying & Huang, 2013;Ying et al, 2014). Compounds based on these ligands easily form three-dimensional structures because there are several coordinating atoms in the ligand.…”

Section: Introductionmentioning

confidence: 99%

Hydrothermal synthesis, crystal structure and photoluminescence of two homochiral zinc(II) coordination polymers

Ying

Luo

2015

Acta Crystallogr C

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Metal-organic frameworks (MOFs) have potentially useful applications and an intriguing variety of architectures and topologies. Two homochiral coordination polymers have been synthesized by the hydrothermal method, namely poly[(μ-N-benzyl-L-phenylalaninato-κ(4)O,O':O,N)(μ-formato-κ(2)O:O')zinc(II)], [Zn(C16H16NO2)(HCOO)]n, (1), and poly[(μ-N-benzyl-L-leucinato-κ(4)O,O':O,N)(μ-formato-κ(2)O:O')zinc(II)], [Zn(C13H18NO2)(HCOO)]n, (2), and studied by single-crystal X-ray diffraction, elemental analyses, IR spectroscopy and fluorescence spectroscopy. Compounds (1) and (2) each have a two-dimensional layer structure, with the benzyl or isobutyl groups of the ligands directed towards the interlayer interface. Photoluminescence investigations show that both (1) and (2) display a strong emission in the blue region.

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Section: Introductionmentioning

confidence: 99%

Hydrothermal synthesis, crystal structure and photoluminescence of two homochiral zinc(II) coordination polymers

Ying

Luo

2015

Acta Crystallogr C

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“…[13][14][15][16] One such set of ligands that has been utilized to some extent are the reduced Schiff base ligands of various amino acids. [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] However, their use in making coordination architectures under hydrothermal conditions is limited due to their poor thermal stability. 35 L-Tyrosine is one of the few amino acids with three functional groups (hydroxy, amino and carboxylate) that can provide diverse binding modes (chelating, bridging, etc.…”

Section: Introductionmentioning

confidence: 99%

Controlling the self-assembly of homochiral coordination architectures of Cu^II by substitution in amino acid based ligands: synthesis, crystal structures and physicochemical properties

2015

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Through the strategic design of ligands based on amino acids, structural diversity in chiral coordination architectures of CuII is demonstrated with six new examples: {[Cu(L-HTyrbenz)2]·CH3OH·H2O}n (1), {[Cu(L-HSerbenz)2]·3H2O}n (2), {[Cu(L-HTyrthio)2]·H2O}n (3), [Cu(L-HTyr4-pyr)2(H2O)]·2H2O (4), [Cu(L-HSerthio)2(H2O)] (5), and [Cu(L-Phethio)2(H2O)]·3H2O (6) [where L-H2Tyrbenz = L-N-(benzyl)-tyrosine, L-H2Serbenz = L-N-(benzyl)-serine, L-H2Tyrthio = L-N-(methyl-2-thiophenyl)-tyrosine, L-H2Tyr4-pyr = L-N-(methyl-4-pyridyl)-tyrosine, L-H2Serthio = L-N-(methyl-2-thiophenyl)-serine and L-HPhethio = L-N-(methyl-2-thiophenyl)-phenylalanine]. For these 1:2 metal–ligand complexes, the availability of a donor atom (either from the phenolic OH group or the carboxylate group of one of the ligands) for bridging between the CuII centers results in the formation of coordination polymers (1–3), while no such availability allows a water molecule to occupy the fifth site around the CuII center to generate hydrogen bonded supramolecular assemblies (4–6). In 1, a coordination polymer is formed via a syn–anti bridging carboxylate, and the phenolic group has no role in its formation. To further emphasize this point, L-tyrosine in 1 is replaced with L-serine to form 2, in which an anti–anti bridging by the carboxylate group is observed. On the other hand, the formation of {[Cu(L-HTyrthio)2]·H2O}n (3) results from the growth of a spiral polymer via the unique phenolic bridging with a distance of 10.806(9) Å between two CuII centers. On changing from the L-H2Tyrbenz ligand to the L-H2Tyr4-pyr ligand (1vs.4), the strong hydrogen bonding of the pyridyl nitrogen with the phenolic group does not allow the latter to bind to CuII. Similarly, on changing from L-H2Tyrthio to L-H2Serthio (3vs.5), the length of the –CH2OH group in the latter is much less than the distance between the two CuII centers, therefore this group cannot occupy the fifth site and thus a water molecule is coordinated. This is further confirmed by reacting 5 with 2 eq. of L-H2Tyrthio in methanol to form 3, while the reverse is not possible. All these compounds are characterized by a number of analytical methods, such as elemental analysis, FTIR, UV-Vis and circular dichroism spectroscopy, polarimetry, powder and single crystal X-ray diffraction and thermogravimetric analysis. Photoluminescence properties of all ligands containing the L-tyrosine group and their metal complexes (1, 3 and 4) are compared in solution at room temperature.

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“…We can obtain reduced Schiff base ligands of this type by reacting amino acids, having a chiral C atom, with 4-carboxybenzaldehyde to obtain the corresponding Schiff bases and then reducing the C N bond. Up to now, to the best of our knowledge, there are still only a few NCS compounds based on reduced Schiff base ligands of this type (Yang et al, 2011;Ying, 2012;Ying & Huang, 2013). In order to study the form of the NCS compounds which are induced by reduced Schiff base ligands of this type, we have synthesized a chiral reduced Schiff base ligand formed by 4carboxybenzaldehyde with l-phenylalanine, namely 4-{[(1carboxy-2-phenylethyl)amino]methyl}benzoic acid (H 2 L), and two NCS compounds have been obtained using this ligand, namely poly 1S)…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structures and characterizations of two homochiral coordination polymers based on a chiral reduced Schiff base ligand

et al. 2014

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Two homochiral coordination polymers based on a chiral reduced Schiff base ligand, namely poly[(μ5-4-{[(NR,1S)-(1-carboxylato-2-phenylethyl)amino]methyl}benzoato)zinc(II)], [Zn(C17H15NO4)]n, (1), and poly[(μ5-4-{[(NR,1S)-(1-carboxylato-2-phenylethyl)amino]methyl}benzoato)cobalt(II)], [Co(C17H15NO4)]n, (2), have been obtained by hydrothermal methods and studied by single-crystal X-ray diffraction, elemental analyses, powder X-ray diffraction, thermogravimetric analysis, IR spectroscopy and fluorescence spectroscopy. Compounds (1) and (2) are isostructural and crystallize in the P2(1)2(1)2(1) space group. Both display a three-dimensional network structure with a one-dimensional channel, with the benzyl group of the ligand directed towards the channel. An investigation of photoluminescence properties shows that compound (1) displays a strong emission in the purple region.

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Syntheses, crystal structures, and characterization of four homochiral coordination polymers based on two chiral reduced Schiff base ligands

Cited by 4 publications

References 26 publications

Hydrothermal synthesis, crystal structure and photoluminescence of two homochiral zinc(II) coordination polymers

Hydrothermal synthesis, crystal structure and photoluminescence of two homochiral zinc(II) coordination polymers

Controlling the self-assembly of homochiral coordination architectures of Cu^II by substitution in amino acid based ligands: synthesis, crystal structures and physicochemical properties

Synthesis, crystal structures and characterizations of two homochiral coordination polymers based on a chiral reduced Schiff base ligand

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Syntheses, crystal structures, and characterization of four homochiral coordination polymers based on two chiral reduced Schiff base ligands

Cited by 4 publications

References 26 publications

Hydrothermal synthesis, crystal structure and photoluminescence of two homochiral zinc(II) coordination polymers

Hydrothermal synthesis, crystal structure and photoluminescence of two homochiral zinc(II) coordination polymers

Controlling the self-assembly of homochiral coordination architectures of CuII by substitution in amino acid based ligands: synthesis, crystal structures and physicochemical properties

Synthesis, crystal structures and characterizations of two homochiral coordination polymers based on a chiral reduced Schiff base ligand

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Controlling the self-assembly of homochiral coordination architectures of Cu^II by substitution in amino acid based ligands: synthesis, crystal structures and physicochemical properties