Structural versatility of four coordination polymers based on 5-(1-oxoisoindolin-2-yl)isophthalic acid: Magnetic and luminescent properties

Inorganica Chimica Acta 453 (2016) 8–15

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Research paper

Structural versatility of four coordination polymers based on 5-(1-oxoisoindolin-2-yl)isophthalic acid: Magnetic and luminescent properties Run-Ping Ye a,b, Ling Lin a, Yuan-Gen Yao a,⇑ a Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, PR China b University of Chinese Academy of Sciences, Beijing 100049, PR China

a r t i c l e

i n f o

Article history: Received 6 June 2016 Received in revised form 25 July 2016 Accepted 26 July 2016 Available online 27 July 2016 Keywords: Coordination polymers Crystal structure Magnetism Luminescence Quantum yield

a b s t r a c t Four interesting coordination polymers, namely [Co(IDPA)(phen)(H2O)]n (1), [Co(IDPA)(bpp)(H2O)]n
2n (H2O) (2), [Zn(IDPA)(py)]n (3), and [Pb(IDPA)(H2O)]n (4) (H2IDPA = 5-(1-oxoisoindolin-2-yl)isophthalic acid, phen = 1,10-phenanthroline, bpp = 1,3-bis(4-pyridyl)propane, py = pyridine), have been successfully synthesized under solvothermal conditions and structurally characterized. Single-crystal X-ray diffraction analyses indicate that compound 1 shows a zigzag chain, while compounds 2–4 exhibit two-dimensional wavelike or flat layer structures with the same uninodal 4-connected sql topology. These results reveal that different metal centers with the presence of auxiliary ligands maybe play a significant role in the construction process of coordination polymer. Furthermore, compounds 1 and 2 display weak antiferromagnetic interactions in the system. Interestingly, because H2IDPA is a coplanar ligand with large rigid p-conjugated system, it exhibits a strong blue emission with the quantum yield (QY) up to 4.41%. Furthermore, compound 3 is a 2D layer structure and its QY is largely increased to 22.52%. Besides, compound 4 shows a multiple emissions from blue to yellow and falls within the white region of the 1931 CIE chromaticity diagram. Therefore, it is suggested to turn on the fluorescence by building the fluorophore within metal-organic frameworks. Ó 2016 Elsevier B.V. All rights reserved.

1. Introduction Recently, it is highly appealing to develop high performance of white-light-emitting materials and devices, which have enormous potential applications in lighting and displays [1–3]. Generally, the diverse structures and outstanding properties of such materials greatly depend on the reasonable selection of the organic spacers and metal centers, as well as on the reaction conditions [4–8]. Therefore, ligands with certain functional groups, such as carboxylate, phosphate, and pyridyl are especially crucial and have been widely explored [9–13]. On the one hand, the 5-(1-oxoisoindolin-2-yl)isophthalic acid (H2IDPA) ligand has a large rigid p-conjugated system in which aromatic substituent is coplanar with the benzene ring (Scheme 1), with the aim of facilitating and enhancing p electrons delocalization in the ligand. As a result, potentially luminescent ligand-toligand charge transfer (LLCT) and ligand-to-metal charge transfer (LMCT) are more likely to happen. On the other hand, auxiliary ⇑ Corresponding author. E-mail address: [email protected] (Y.-G. Yao). http://dx.doi.org/10.1016/j.ica.2016.07.045 0020-1693/Ó 2016 Elsevier B.V. All rights reserved.

N-donor building blocks, such as the traditionally employed 4,40 bipyridine, 2,20 -bipyridine and 1,10-phenanthroline (phen) have been extensively studied in coordination chemistry [14–16]. Herein, we have focused intensively on mixed-ligands to elaborate considerable diverse coordination polymers (CPs) with the help of three different N-donor ligands including phen, bpp and py (bpp = 1,3-bis(4-pyridyl)propane, py = pyridine), as shown in Scheme 1. Several CPs based on H2IDPA ligand have been obtained with Zn/CdII metals by us before [17]. With the aim of further understanding the coordination chemistry of this novel ligand and preparing new materials with excellent magnetic properties and interesting luminescence performance, our recent work have been dedicated to synthesizing CPs based on it. To the best of our knowledge, the change of metal ions may construct strikingly different structures because that the metal ions with different electronic configurations could show different coordination modes toward the same ligand [18–21]. Employing this strategy, we have successfully prepared four interesting CPs with three different metal ions under solvothermal reactions, namely [Co(IDPA)(phen)(H2O)]n (1), [Co(IDPA)(bpp)(H2O)]n
2n (H2O) (2), [Zn(IDPA)(py)]n (3), and [Pb(IDPA)(H2O)]n (4). Interest-

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Scheme 1. Schematic molecular structures of H2IDPA, phen, bpp and py ligands.

ingly, free H2IDPA ligand exhibits a strong blue emission, while the combination of H2IDPA and PbII ions into a rigidified 2D matrix results in a white-light emitting property, which affords a new approach to attain white-light-emission from single component CPs [22–24]. Furthermore, by building the H2IDPA within metalorganic frameworks, the quantum yield (QY) could be enhanced from 4.41% (free H2IDPA ligand) to 22.52% (compound 3). In addition, the synthesis, crystal structures, thermal stabilities and FT-IR spectra of these compounds have been studied in detail. 2. Experimental 2.1. Materials and physical measurements All the reagents and solvents used in the syntheses were commercially available and used without further purification. Elemental analyses of C, H, and N were performed on a Vario EL-Cube elemental analyzer. The FT-IR spectra were recorded by a Bruker Vertex 70 FT-IR in the region 4000–400 cm1 using KBr pellets (Fig. S1 in the Supporting Information). The temperature-dependent magnetic susceptibility of compounds 1 and 2 were performed on a Quantum Design Physical Property Measurement System (PPMS) at 2–300 K with an external field of 1000 Oe. The luminescence spectra of compounds 3 and 4 were measured at 298 K with a FLS980 produced by EDINGBURGH INSRUMENTS. The quantum yield (QY) measurements were performed on a FLS920 produced by EDINGBURGH INSRUMENTS by means of an integrating sphere. The QY value is equal to the ratio of the number of emitted photons and the number of absorbed photons. The absolute error on the QY values is about ±1%.

57.19, H 4.69, N 7.14%. IR/cm1 (KBr): 3439 (m), 1686 (m), 1559 (s), 1369 (s), 1158 (w), 815 (w), 778 (s), 731 (s). 2.4. Synthesis of [Zn(IDPA)(py)]n
(3) A mixture of Zn(NO3)2
6H2O (0.059 g, 0.20 mmol), H2IDPA (0.030 g, 0.10 mmol), NaOH (0.50 mL, 0.50 mol/L) and three drops of pyridine in a 20 mL capped vial, DMF (1 mL) and H2O (2 mL) were then added. The resulting mixture was stirred for 30 min at room temperature, and then heated at 90 °C for two days. After a slow cooling to room temperature, colorless rod crystals of 3 were obtained by filtration with the yield of 0.021 g, 48% (based on H2IDPA ligand). Anal. calcd for C21H14ZnN2O5: C 57.31, H 3.18, N 6.37%. Found: C 57.34, H 3.28, N 6.55%. IR/cm1 (KBr): 3122 (w), 1692 (s), 1580 (s), 1348 (s), 1143 (m), 778 (m), 731 (s), 694 (s). 2.5. Synthesis of [Pb(IDPA)(H2O)]n (4) A mixture of Pb(NO3)2 (0.066 g, 0.20 mmol), H2IDPA (0.030 g, 0.10 mmol) and one drop of concentrated HNO3 in DMF (2 mL) and H2O (1 mL) was stirred at room temperature for 30 min after which the mixture was transferred to a 20 mL capped vial and heated at 90 °C for two days. After a slow cooling to room temperature, colorless needle-shaped crystals of 4 were obtained by filtration with the yield of 0.030 g, 57% (based on H2IDPA ligand). Anal. calcd for C16H11PbNO6: C 36.89, H 2.11, N 2.69%. Found: C 37.14, H 2.34, N 2.88%. IR/cm1 (KBr): 3471 (w), 1675 (m), 1528 (s), 1390 (s), 1164 (w), 783 (m), 738 (m), 694 (w). 2.6. X-ray crystallographic studies

A mixture of Co(NO3)2
6H2O (0.058 g, 0.20 mmol), H2IDPA (0.030 g, 0.10 mmol), phen (0.018 g, 0.10 mmol) and NaHCO3 (0.50 mL, 0.50 mol/L) in DMF (1 mL, DMF = N,N-dimethylformamide) and H2O (2 mL) was stirred at room temperature for 30 min after which the mixture was transferred to a 20 mL capped vial and heated at 90 °C for two days. After a slow cooling to room temperature, purple block crystals of 1 were separated by filtration with the yield of 0.029 g, 52% (based on H2IDPA ligand). Anal. calcd for C28H19CoN3O6: C 60.83, H 3.44, N 7.60%. Found: C 61.01, H 3.51, N 7.55%. IR/cm1 (KBr): 3092 (w), 1697 (s), 1576 (s), 1354 (s), 1148 (w), 857 (s), 778 (m), 725 (s).

The single-crystal X-ray diffraction data of compounds 1–4 were collected at 298 K using a computer-controlled Oxford Xcalibur E diffractometer with graphite monochromatic Mo-Ka radiation (k = 0.71073 Å). The structures were solved by Direct Methods and refined by full-matrix least-squares on F2 using the SHELXL-97 crystallographic software package [25,26]. Non-hydrogen atoms were refined anisotropically and hydrogen atoms were added geometrically and refined using a riding model. In compound 4, due to the disorder of O5, the O5 atom has two possible conformers with O5A and O5B appearing with 50% probability. Crystallographic data and refinement parameters for compounds 1–4 are given in Table 1. Selected bond lengths and bond angles are summarized in Table S1.

2.3. Synthesis of [Co(IDPA)(bpp)(H2O)]n
2n(H2O) (2)

3. Results and discussion

Compound 2 was prepared similarly to 1, except that phen (0.018 g, 0.1 mmol) was replaced by bpp (0.020 g, 0.10 mmol). Purple block crystals suitable for single-crystal X-ray diffraction were collected with the yield of 0.040 g, 65% (based on H2IDPA ligand). Anal. Calcd. for C29H29CoN3O8: C 57.38, H 4.78, N 6.93%. Found: C

3.1. Description of crystal structures

2.2. Synthesis of [Co(IDPA)(phen)(H2O)]n (1)

3.1.1. Structure of [Co(IDPA)(phen)(H2O)]n (1) Single crystal X-ray diffraction analysis reveals that compound 1 crystallizes in the monoclinic space group P21/c with one

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Table 1 Crystallographic data and structure refinement for compounds 1–4.

a b

Compound

1

2

3

4

Empirical formula Crystal color Formula weight Crystal system Space group a (Å) b (Å) c (Å) a (°) b (°) c (°) V (Å3) Z Dcalcd (g cm1) l (mm1) F(0 0 0) Rint [I > 2h] Rw2 [I > 2h] Rint alla Rw2 allb S

C28H19CoN3O6 Purple 552.39 Monoclinic P21/c 10.6361(5) 14.3793(7) 15.5138(6) 90.00 100.519(4) 90.00 2332.80(18) 4 1.573 0.788 1132.0 0.0583 0.1669 0.0880 0.2431 1.053

C29H29CoN3O8 Purple 606.45 Monoclinic P2/c 11.7771(9) 9.9537(9) 23.4311(17) 90.00 97.546(6) 90.00 2722.9(4) 2 1.450 0.685 1228.0 0.0694 0.1597 0.1141 0.1813 1.069

C21H14ZnN2O5 Colorless 439.73 Orthorhombic Pbca 9.9330(3) 15.7732(5) 23.0344(7) 90.00 90.00 90.00 3608.92(19) 8 1.619 1.399 1792.0 0.0297 0.0703 0.0354 0.0738 1.036

C16H11PbNO6 Colorless 520.43 Triclinic P1 3.8507(2) 10.1610(9) 20.8086(18) 96.824(7) 93.752(6) 92.956(6) 805.23(11) 2 2.130 10.507 480.0 0.0474 0.1157 0.0664 0.1285 1.043

Rint = R||Fo|  |Fc||/R|Fo|. Rw2 = [Rw(F2o  F2c )2/Rw(F2o)2]1/2.

crystallographically independent Co(II) ion, one IDPA2 ligand, one phen ligand and one coordinated water molecule in the asymmetric unit. As shown in Fig. 1a, the Co1 atom shows a distorted trigonal bipyramidal coordination geometry which is surrounded by two nitrogen atoms from phen ligand, two oxygen atoms from IDPA2 ligand and one oxygen atom from water molecule. Here, two carboxylate groups of the IDPA2 ligand bind in the same mode: l1-g1-bridging (Scheme 2a). The adjacent Co1 ions are bridged by carboxylate groups of IDPA2 ligands and chelated by phen ligands, thus forming an infinite zigzag 1D chain (Fig. 1b). Furthermore, it is worth noting that the individual zigzag chains are connected into a 3D intricate network by hydrogen bonds (Fig. 1c).

3.1.2. Structure of [Co(IDPA)(bpp)(H2O)]n
2n(H2O) (2) A single-crystal X-ray diffraction study of 2 reveals a 2D layer that crystallizes in monoclinic space group P2/c. The asymmetric unit of 2 contains one crystallographically independent Co(II) ion, one IDPA2 ligand, one bpp ligand, one terminal H2O ligand and two free water molecules. As shown in Fig. 2a, the Co1 atom is seven-coordinate comprising one coordinated water molecule, four oxygen atoms from two IDPA2 ligands and two nitrogen atoms from two bpp ligands. Compared to 1, there is one different coordination mode of the IDPA2 ligand in 2: l1-g2-chelating (Scheme 2b). As shown in Fig. 2b, the adjacent Co1 ions are bridged by IDPA2 and bpp ligands to generate a 40-number metallomacrocycle [Co4(IDPA)2(bpp)2]. Within the metallomacrocycle, the non-

Fig. 1. (a) Coordination environment around the Co(II) ions in 1. (b) A 1D zigzag chain of 1. (c) The 3D supramolecular framework of 1 via hydrogen bonds (the dashed lines in picture). [Symmetry codes: (i) x + 1, y  1/2, z + 3/2 for O3A.]

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Scheme 2. The coordination modes of the H2IDPA ligand in compounds 1–4. [(a)–(d) for 1–4, respectively.]

bond Co


Co separations are 10.0 and 11.8 Å. These metallomacrocycles link each other into a 2D wavelike layer (Fig. 2d), which further extends to a 3D interlaced framework via p–p interactions (Figs. 2e and S2 in the Supporting Information). As shown in Fig. 2c, the distances of intermolecular p–p interactions (two planes of C3


C4


C5


C6


C7


C8, two planes of N3


C9


C12


C11


C10, planes between N3


C9


C12


C11


C10 and C11


C12


C13


C14


C15


C16) are 3.5, 3.7, and 3.9 Å, respectively (PLATON) [27], which are in accordance with previous reports [28,29]. In addition, the 2D sheet can be described as a uninodal 4-connected sql net with the Schläfli symbol of {44
62} (Fig. 2d). 3.1.3. Structure of [Zn(IDPA)(py)]n (3) Compound 3 crystallized in orthorhombic space group Pbca. Its asymmetric unit contains only one crystallographically independent Zn(II) center, one IDPA2 ligand and one py ligand. As shown in Fig. 3a, Zn1 exhibits a trigonal bipyramidal geometry which is coordinated by four carboxylate oxygen atoms from three distinct IDPA2 ligands and one nitrogen atom from a py ligand. In 3, the [Zn2(COO)4(py)2] building unit is constructed and four such units are connected through IDPA2 ligands into a rhomboic

metallomacrocycle (Figs. 3b and S3 in the Supporting Information), whose diagonal Zn1–Zn1A and Zn1B–Zn1C separations are 9.9 and 15.8 Å [(i) 1 + x, y, z for Zn1A; (ii) 1.5  x, 0.5 + y, z for Zn1B; (iii) 1.5  x, 0.5 + y, z for Zn1C]. As shown in Scheme 2c, two carboxylate groups of the IDPA2 ligand bind in two different modes: l1-g2-chelating and l2-g1:g1-bridging. Because each [Zn2(COO)4(py)2] building unit acts as a 4-connected node, the flat 2D layer of 3 presents a sql net with the Schläfli symbol of {44
62} (Fig. 3c and d). 3.1.4. Structure of [Pb(IDPA)(H2O)]n (4) Compound 4 was obtained without auxiliary ligand, which was also a 2D layer structure (Fig. 4b–c). The single X-ray diffraction study analysis reveals that compound 4 crystallizes in the triclinic space group P1. As shown in Fig. 4a, the Pb1 center adopts a slightly distorted seven-coordinated geometry which is completed by six oxygen atoms from five different IDPA2 ligands and one oxygen atom from water molecule. As shown in Scheme 2d, two carboxylate groups of the IDPA2 ligand display two more complicated coordination modes: l2-g2-chelating:g1-bridging and l3g2-bridging:g1-bridging. Just like the previous one, each binuclear building unit links four other units to form a 2D layer with the

Fig. 2. (a) Coordination environment around the Co(II) ions in 2. (b) The metallomacrocycle [Co4(IDPA)2(bpp)2] in 2. (c) The intermolecular p–p interactions in 2. (d) The 4connected wavelike topology of 2 viewed from the c-axis. (e) The 3D supramolecular network of 2. [Symmetry codes: (i) x  1, y, z for N2A; (ii) x, y  1, z for O3B and O4B.]

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Fig. 3. (a) Coordination environment around the Zn(II) ions in 3. (b) The rhomboic metallomacrocycle in 3. (d) The 2D layer of 3 viewed from the c-axis. (d) Schematic representation of the 4-connected topology of 3. [Symmetry codes: (i) x + 1, y, z + 1 for O2B; (ii) x + 3/2, y + 1/2, z for O3A and O4A.]

Fig. 4. (a) Coordination environment around the Pb(II) ions in 4. (b) The 2D layer of 4 viewed from the a-axis. (d) The 2D layer of 4 viewed from the c-axis. (d) Schematic representation of the 4-connected topology of 4. [Symmetry codes: (i) x + 1, y + 2, z + 1 for O3a and O4a; (ii) x + 1, y + 1, z + 1 for O2b; (iii) x + 2, y + 2, z + 1 for O3c.]

same Schläfli symbol of {44
62}, as shown in Fig. 4d. The resulting layers are parallel to each other and stack into a 3D dense framework with an A–B–A mode (Fig. S4 in the Supporting Information).

3.2. Thermal analysis and powder X-ray diffraction The thermal behaviors for compounds 1–4 were studied to reveal their thermal stabilities. Thermogravimetric analysis (TGA)

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3.3. Magnetic properties for 1 and 2

Fig. 5. The TGA curves of compounds 1–4.

experiments were performed on pure single crystal sample of 1–4 under N2 atmosphere with a heating rate of 10 °C
min1 in the range of 30–990 °C. The thermal curves are exhibited in Fig. 5. Compound 1 displays the weight loss by stage owing to the release of coordinated water molecules in the range from 198 to 238 °C (obsd: 3.35%, calcd: 3.26%). The organic spacers then decompose after 329 °C. The TGA curve of 2 shows the weight loss of 8.21% between 80 and 165 °C, corresponding to the loss of three water molecules per unit cell (calcd: 8.90%), which is followed by a steady plateau up to 273 °C. For 3, there is no mass change from room temperature to 90 °C on the whole, and the weight-loss from 90 to 320 °C can be ascribed to the release of coordinated pyridine molecules (obsd: 18.09%, calcd: 17.99%). According to the TGA curve of 4, the free water molecules are lost in the range of 80– 125 °C (obsd: 3.77%, calcd: 3.46%), and the organic components break down after 290 °C as well. In addition, to check the phase purities and homogeneities of compounds 1–4, the four compounds were characterized by X-ray powder diffraction (XRPD) on a MiniFlex-II diffractometer with Cu-Ka radiation (k = 1.54056 Å) with a step size of 5°/min at room temperature. As shown in Fig. S5 in the Supporting Information, the peak positions of the experimental patterns are in good agreement with the simulated ones, which clearly indicate good purities and homogeneities of the compounds.

The solid-state direct-current magnetic susceptibilities of 1 and 2 were measured over the temperature range of 2–300 K under an outer field of 1000 Oe. The changing tendencies for temperature dependence of magnetic susceptibility are shown as v and v1 versus T plots in Fig. 6. The reciprocal susceptibility plots are linear and follow the Curie-Weiss law in the range of 2–300 K, v = C/ (T  h), with the Curie constant C = 2.44, 5.02 emu mol1 K and the Weiss temperature h = 3.47, 5.43 K for 1 and 2, respectively. Because the bridging ligands H2IDPA and bpp are quite long, and thus the Co


Co distances are a little long too, resulting the weak magnetic interaction transferred by these ligands. The small negative h value indicates that the overall magnetic interactions among the Co(II) ions are weakly antiferromagnetic, which are probably due to the single ion anisotropy and antiferromagnetic exchange between the ions centers [18]. Furthermore, the detailed magnetic analyses of the similar compounds can be found in References [13,30,31].

3.4. Luminescent properties for 3 and 4 Luminescent coordination polymers have been receiving great attention owning to their potential application in photochemistry, chemical sensors and electroluminescent display [11,32,33]. Hence, the photoluminescence properties of compounds 3 and 4, together with the free H2IDPA ligand were investigated in the solid-state at room temperature. As shown in Fig. 7a, compounds display strong single blue emission band centered at 439 nm (kex = 365 nm) for H2IDPA and 434 nm (kex = 380 nm) for 3, which can be probably attributed to p to p⁄ or n orbital transitions of intraligand nature [12,34,35]. However, 4 shows two major emission peaks centered at 435 and 530 nm, and one shoulder peak at 560 nm upon an excitation of 360 nm. The first emission peak at 435 nm can be assigned to the intraligand fluorescent emission while the other two peaks may be ascribed to LLCT, LMCT and the metal-ligand coordination interactions [36,37]. These multiple emissions give a calculated chromaticity coordinate at (0.30, 0.35), just falling within the white region of the 1931 CIE chromaticity diagram (Fig. 7b). In addition, further research on quantum yield (QY) of H2IDPA, 3 and 4 was carried on and shown in Fig. 8. The QY increases largely from 4.41% of free H2IDPA ligand to 22.52% of 3. It may be attributed to the ligand coordination to the metal center, forming a rigidified 2D layer matrix, which

Fig. 6. Temperature dependencies of the magnetic susceptibility (v) and corresponding reciprocal value (v1) in the temperature range 2–300 K for compounds 1 (a) and 2 (b).

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Fig. 7. (a) The emission spectra of free H2IDPA ligand and compounds 3–4 in the solid state at room temperature. (b) The photograph of the CIE chromaticity diagram for them.

Fig. 8. The quantum yield curves of free H2IDPA ligand (a) and compound 3 (b).

extends the conjugated system and restricts the rotation of the phenyl rings, as well as facilitating the transition of p-electrons and decreasing the loss of energy [38–40]. However, photoluminescent efficiency of 4 is slightly enhanced to 5.10% probably owing to the coordinated water molecules in 4 which may efficiently quench the fluorescence of compounds through highenergy OAH oscillators (Fig. S6 in the Supporting Information) [5,41].

between the CoII ions in 1 and 2. Meanwhile, 3 and 4 exhibit advantageous luminescent properties, including intense emissions and high quantum yields, which stem from the ligand coordination to the metal center, forming a rigidified 2D layer matrix. The further research works are underway based on H2IDPA and the same transition metals.

4. Conclusions

This work was supported by the ‘‘Strategic Priority Research Program” of the Chinese Academy of Sciences (XDA07070200, XDA09030102), the Science Foundation of Fujian Province (2006l2005) and Fujian industrial guide project (2015H0053).

In summary, four new CPs constructed from CoII, ZnII and PbII salts and 5-(1-oxoisoindolin-2-yl)isophthalic acid with the help of phen, bpp and py are reported, and magnetic behaviors of 1, 2 as well as the fluorescence properties of 3, 4 were also studied. Compound 1 shows a zigzag chain while compounds 2–4 feature three different layers, which extend into 3D frameworks via hydrogen bonds or p–p interactions. Therefore, structural investigation demonstrates that the nature of the metal ions and auxiliary ligands influence the formation of CPs. Interestingly, magnetic measurements showed that a weak antiferromagnetic interaction

Acknowledgements

Appendix A. Supplementary data CCDC 1473041–1473044 contain the supplementary crystallographic data for the compounds 1–4. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Supplementary data

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