Abstract
The complex [Pb(phen)(4-NB)(CH3COO)] of lead(II) was prepared and characterized by means of elemental analysis, FT-IR, and single crystal X-ray analysis, where phen = 1,10-phenanthroline, 4-NB = 4-nitrobenzoate. The single crystal X-ray analysis indicates that the complex is a monomeric species, including two carboxylate ligands, and adopts a hemidirected structure. It is further extended by intermolecular C−H⋯O hydrogen bonds, π–π interactions and secondary Pb⋯O interactions to form two-dimensional supramolecular architecture.
The coordination chemistry of lead(II) with N and O donor ligands has been studied extensively in recent years because of their intriguing structures and potential applications in some fields, such as luminescence, organic light-emitting diode, catalysis, nano materials, and antimicrobial (Alizadeh and Amani, 2011; Ding et al., 2008; Jin, 2020; Kazak et al., 2009; Kowalik et al., 2020; Li, 2019; Ma et al., 2018; Mirtamizdoust, 2017; Najafi et al., 2013; Sahu et al., 2013; Singh et al., 2016; Song et al., 2018; Wang et al., 2014; Xiong et al., 2012; Yang et al., 2016; Zhang et al., 2011; Zhao et al., 2007). Lead(II) has an electron configuration of [Xe]4f145d106s2, with large ionic radius. It is able to form compounds with broad range of coordination numbers (Balch and Oram, 1987; Du et al., 2006; Fan and Zhu, 2006; Jin et al., 2010; Li et al., 2012). Due to the presence of the 6s lone-pair electrons, which may or may not be stereochemically active, PbII complexes display either hemidirected or holodirected structures. The lone pair electron on lead(II) is stereochemically inactive and ligand-to-metal bonds are distributed evenly around the lead(II) ion is termed holodirected, otherwise it is called hemidirected (Janiak et al., 2000; Pellissier et al., 2007; Shimoni-Livny et al., 1998). Secondary bonds, as a kind of non-covalent interaction, usually existed in the hemidirected lead(II) complexes and formed by the stereochemically active lone pair, such as Pb⋯O, Pb⋯N, Pb⋯C, Pb⋯Cl, Pb⋯S, and Pb⋯π, which have some effect on the structures and properties of the lead(II) complexes (Catalano et al., 2015; Chen et al., 2015; Cheng et al., 2014b; Huang et al., 2017; Kowalik et al., 2020; Meng et al., 2009; Miao and Zhu, 2008; Mirdya et al., 2019, 2020; Yang et al., 2012; Zhao et al., 2007). Thus, Pb2+ ion is an ideal candidate for the construction of novel complexes (including monomeric compounds and metal–organic frameworks). In the reported lead(II) complexes, a number of compounds were tested for fluorescence properties, and the presence or absence of stereochemically active lone-pair Pb(II) has possible effect on luminescence of coordination compounds (Chen et al., 2015; Katz et al., 2008; Meng et al., 2009; Nugent et al., 2015). Therefore, some Pb(II) complexes exhibiting good luminescent properties have been observed (Alizadeh and Amani, 2011; Ding et al., 2008; Kowalik et al., 2020; Li, 2019; Ma et al., 2018; Sahu et al., 2013; Song et al., 2018; Xiong et al., 2012; Yang et al., 2016; Zhang et al., 2011; Zhao et al., 2007). Lead(II) compounds having catalytic and antimicrobial activities, fabricating organic light-emitting diode and nano materials have also been occasionally reported. For example, Wang et al. (2014) reported eleven germanium(II), tin(II), and lead(II) amino-(ether)-phenolate monomeric complexes and nine of them in the catalysis of the immortal ring-opening polymerisation (iROP) of l-lactide (l-LA) or racemic-lactide (rac-LA) upon addition of iPrOH were tested, it is surprised to find the catalytic activity increases with metal size according to GeII « SnII » PbII. Singh et al. (2016) reported lead(II) complexes with semicarbazone and thiosemicarbazones derived from (2-hydroxyphenyl) (pyrrolidin-1-yl)methanone assessed as antibacterial and antifungal agents and the results interestingly showed the lead(II) complexes have higher activity than the free ligands. Najafi et al. (2013) synthesized a new complex, [Pb(μ-8-Quin)I]2, and fabricated OLEDs by the prepared complex. The experiment results demonstrated the complex dye can serve as an electron transport layer and light emission layer along with the PVK as a hole transport layer in organic light-emitting diodes. Mirtamizdoust introduced one method of preparing PbO nanoparticles via thermolysis of lead(II) metal-organic coordination polymer (Mirtamizdoust, 2017). Most of the above compounds are constituted with N and O donor ligands. Which may be why Pb(II) compounds are increasingly synthesized and tested in some certain properties despite lead is a heavy toxic metal. 4-Nitrobenzoic acid has two functional groups, carboxyl (−COOH) and nitryl (−NO2), whose carboxylate group can serve as good candidates to tune structures because of their versatile coordination properties, which can bind to metal ions with monodentate, bridging, and chelating modes (Kar et al., 2011; Lv et al., 2019; Ren et al., 2006; Sarma and Baruah, 2009; Tsaryuk et al., 2012; Zhu et al., 2012). In the complexes formed by 4-nitrobenzoate, the nitryl group is generally uncoordinated but its oxygen atom can participate in generating the hydrogen bonds as H-acceptor, which often acts as a contribution in the construction of interesting supramolecular architectures (Ren et al., 2006; Saha et al., 2019; Srinivasan et al., 2009; Xu et al., 2012). Moreover, the introduction of the neutral ligands can adjust the coordination modes of 4-nitrobenzoate with metal ions resulting in diverse structures. 1,10-Phenanthroline, as an excellent N-donor bidentate chelating ligand, not only was often used to construct novel fascinating molecular architectures and build supramolecular structures through weak interactions (Liu et al., 2004; Wan et al., 2003), but also to produce compounds of various properties (Erxleben, 2018; Lemercier et al., 2018; Sammes and Yahioglu, 1994). Based on the reasons above mentioned, 4-nitrobenzoic acid was chosen for the construction of novel lead(II) complex containing the ligand 1,10-phenanthroline. Herein we report the preparation and crystal structure of [Pb(phen)(4-NB)(CH3COO)] (Scheme 1), obtained by reactions of lead(II) acetate, 1,10-phenanthroline, and 4-nitrobenzoic acid.
Preparation of the complex.
The molecular structure of the complex determined by single crystal X-ray diffraction method and the result shows that compound crystallizes in the monoclinic P21/n space group, with four formula units in the unit cell, and exhibits monomeric species. As shown in Figure 1a, Pb(II) ion adopts a six-coordinated geometry completed by two nitrogen donors from one 1,10-phenanthroline molecule, two oxygen atoms from one 4-NB ligand, and two oxygen atoms from one acetate ion to generate a N2O4 environment with a deformed pentagonal pyramid, which is like an umbrella. The Pb(II) atom is located in at the top of the umbrella (Figure 1b) and the bond Pb1-O5 is umbrella handle. The Pb1−O bond lengths fall in the range of 2.359(4)–2.656(4) Å (Table 1), which can be well comparable with those in the reported compounds (Lv et al., 2019; Mahjoub and Morsali, 2002; Morsali et al., 2003; Sarma and Baruah, 2009; Xu et al., 2012; Zhao et al., 2013). The Pb1–N bond distances [2.586(5) and 2.658(5) Å] (Table 1) are typical values and are similar to Pb–N bonds in previously published PbII-complexes containing 1,10-phenanthroline ligand (Cheng et al., 2014a; Fan and Zhu, 2006; Mahjoub and Morsali, 2002; Morsali et al., 2003; Xu et al., 2012). IR spectra of the complex were analyzed on the basis of the crystal structure. The band 3049 cm−1 can be assigned to the C−H stretching of phenyl ring. According to IR spectra of the reported complexes [Pb(phen)2(4-NBA)]2·2(NO3)·H2O (Xu et al., 2012) and [Pb(8-OQ)(4-NB)] (Lv et al., 2019), the νas (COO−) and νs (COO−) at 1560 and 1385 cm−1 are attributed to the carboxylate group of 4-nitrobenzoate, the νas (COO−) and νs (COO−) at 1616 and 1427 cm−1 are attributed to the carboxylate group of acetate, respectively. The differences between νas (COO−) and νs (COO−) in the two carboxylate groups are approximately 180 cm−1, which is close to Δν [νas (COO−) – νs (COO−)] values in [Pb(phen)2(4-NBA)]2·2(NO3)·H2O and [Pb(8-OQ)(4-NB)] whose COO− groups adopted chelating mode, indicating the COO− groups from 4-nitrobenzoate and acetate in this complex all chelated Pb(II) ion. The characteristic absorption peaks at 1509 and 1340 cm−1 are assigned to the asymmetric stretching vibration peaks and the symmetric stretching vibration peaks of the NO2 group, respectively. The characteristic peaks of the 1,10-phenanthroline are at about 1404, 832, and 724 cm−1.
The molecular structure of complex at 50% ellipsoids for non-hydrogen atoms.
Selected bond lengths (Å) and angles (deg) for the compound
| Pb1-O1 | 2.656(4) | Pb1-O2 | 2.488(4) |
| Pb1-O5 | 2.359(4) | Pb1-O6 | 2.615(4) |
| Pb1-N1 | 2.586(5) | Pb1-N2 | 2.658(5) |
| O1-Pb1-O2 | 51.09(14) | O1-Pb1-O5 | 77.42(14) |
| O1-Pb1-O6 | 76.52(13) | O2-Pb1-O5 | 80.06(14) |
| O2-Pb1-O6 | 116.35(13) | O5-Pb1-O6 | 52.48(14) |
| O1-Pb1-N1 | 127.28(13) | O1-Pb1-N2 | 149.99(13) |
| O2-Pb1-N1 | 77.15(14) | O2-Pb1-N2 | 134.48(14) |
| O5-Pb1-N1 | 85.39(14) | O5-Pb1-N2 | 75.62(14) |
| O6-Pb1-N1 | 128.23(13) | O6-Pb1-N2 | 76.74(14) |
| N1-Pb1-N2 | 63.17(14) |
In the complex, weak intermolecular hydrogen bonds (Figure 2, Table 2) are observed: (1) One intramolecular C−H⋯O hydrogen bond exists between 1,10-phenanthroline and 4-NB ligand. (2) Four intermolecular C−H⋯O hydrogen bonds are found between 1,10-phenanthroline and two anion (4-NB, CH3COO−) ligands. There are five face to face π–π interactions (Figure 3, Table 3) (Janiak, 2000) between adjacent 1,10-phenanthroline molecules, between 1,10-phenanthroline ligand and 4-NB ligand, between neighboring 4-NB ligands. Finally, these hydrogen bonds and face to face π–π interactions extend the monomer structure into a 2-D supramolecular architecture.
Hydrogen bonds as green dashed lines. Symmetry code: (i) −1+x, y, z; (ii) −1+x, 1+y, z; (iii) 3/2-x, 1/2+y, 1/2-z.
π-π interactions in complex. Symmetry code: (i) 1-x, 2-y, 1-z; (ii) 3/2-x, 1/2+y, 1/2-z; (iii) 2-x, 1-y, 1-z.
H-Bonding geometry parameters (Å and deg) for the compound
| Type | D–H⋯A | D–H (Å) | H⋯A (Å) | D⋯A (Å) | D–H⋯A (deg) |
|---|---|---|---|---|---|
| Intra- | C2–H2⋯O2 | 0.93 | 2.40 | 3.079(8) | 129 |
| Inter- | C4–H4⋯O1i | 0.93 | 2.59 | 3.476(8) | 160 |
| Inter- | C6–H6⋯O6i | 0.93 | 2.42 | 3.326(8) | 165 |
| Inter- | C9–H9⋯O3ii | 0.93 | 2.59 | 3.365(9) | 141 |
| Inter- | C10–H10⋯O5iii | 0.93 | 2.51 | 3.325(7) | 147 |
Symmetry code: (i) −1+x, y, z; (ii) −1+x, 1+y, z; (iii) 3/2-x, 1/2+y, 1/2-z.
π–π interactions for the compound
| Ring (I) → Ring (J) | Centroid to centroid distance (Å) | θ (deg) | Slippage distance (Å) |
|---|---|---|---|
| Cg1 → Cg2 i | 3.710 (3) | 23.3 | 1.465 |
| Cg3 → Cg3 i | 3.543 (3) | 18.0 | 1.095 |
| Cg2 → Cg4 ii | 3.690 (3) | 22.1 | 1.391 |
| Cg3 → Cg4 ii | 3.574 (3) | 16.8 | 1.033 |
| Cg4 → Cg4 iii | 3.570 (3) | 22.2 | 1.351 |
Symmetry code: (i) 1-x, 2-y, 1-z; (ii) 3/2-x, 1/2+y, 1/2-z; (iii) 2-x, 1-y, 1-z. Ring code: Cg1: N1/C1 → C5; Cg2: N2/C8 → C12; Cg3: C1/C5 → C8/C12; Cg4: C14 → C19. θ is the angle between the Ring (I) → Ring (J) vector and the normal to Ring (I).
The complex adopts a hemidirected structure suggesting that 6s lone pair electrons of Pb1 is stereochemically active (Figure 1b) (Janiak et al., 2000; Pellissier et al., 2007; Shimoni-Livny et al., 1998). The direction of Pb1–O and Pb1–N bonds is irregularly distributed through the entire sphere around the lead(II) ion, and an obvious gap trans to the CH3COO− anion can be found in the lead coordination sphere. The coordinating atoms occupy less than a half of a sphere surrounding the lead atom with the dihedral angle of 152.7° between the Pb1 N1 N2 plane and the plane Pb1 O1 O2. In addition, two intermolecular longer secondary Pb⋯O interactions, Pb⋯O4i bond of 3.335 Å and Pb⋯O6ii bond of 3.096 Å (symmetry code i: 2-x, 1-y, 1-z; ii: 2-x, 2-y, 1-z), are discovered (Figure 4) (Huang et al., 2017; Miao and Zhu, 2008), which connect the adjacent [Pb(phen)(4-NB)(CH3COO)] molecular and further stabilize 2-D supramolecular architecture. The values of two Pb⋯O bonds are larger than the sum of the ionic radii but obviously less than the sum of the van der Waals radii (3.54 Å) (Bondi, 1964). The two secondary bonds also confirmed Pb(II) ion adopting hemidirected structure.
Secondary Pb⋯O interaction shown as green dashed lines. Symmetry code: (i): 2-x, 1-y, 1-z; (ii): 2-x, 2-y, 1-z.
The Pb(II) complex based on 1,10-phenanthroline and 4-nitrobenzoic acid with the Pb(CH3COO)2 was obtained and structurally characterized. The compound was a monomeric species involving hemidirected Pb(II) atom, and displayed 2-D supramolecular architecture constructed via intermolecular hydrogen bonds, π–π interactions and secondary Pb⋯O interactions. In this complex, the coordinate bonds around Pb(II) ion and non-covalent interactions probably affect the energy transfer and improve the luminescence properties of the compound compared with those of the free ligands.
Experimental
A mixture of Pb(CH3COO)2·3H2O (0.1910 g, 0.50 mmol), 1,10-phenanthroline monohydrate (0.1980 g, 1.0 mmol), 4-nitrobenzoic acid (0.1671 g, 1.0 mmol) and NaOH (0.0400 g, 1.0 mmol) in a water/DMF/methanol (2:1:1, v/v/v) solution (20 mL) was refluxed for 4 h and filtered. Yellow block crystals were obtained after 23 days. All materials were commercially available and were of reagent grade. Yield: 47%. Elemental analyses of carbon, hydrogen, and nitrogen were carried out with a Perkin-Elmer 2400II element analyzer (PerkinElmer, Waltham, MA, USA). Elemental analysis calcd. (%) for C21H15N3O6Pb: C, 41.14; H, 2.45; N, 6.86. Found: C, 41.25; H, 2.43; N, 6.89. Fourier transform IR (FTIR) spectra were recorded on a Nicolet-iS10 spectrophotometer (Thermo Fisher Scientific, Waltham, MA, USA) (range, 400–4000 cm−1) as KBr pellets. IR (KBr, cm−1): 3049m, 1654w, 1616m, 1560s, 1509s, 1427s, 1404s, 1385s, 1340s, 1321m, 1222w, 1147w, 1106m, 1048w, 1014w, 930w, 880w, 860m, 832s, 796w, 780w, 724s, 709w, 670m, 634w, 619w, 516s.
X-ray crystallography
Single-crystal X-ray diffraction data was obtained using Agilent SuperNova diffractometer equipped with an Atlas CCD detector (Agilent Technologies Inc, Santa Clara, CA, USA) at 145(1) K with graphite monochromated MoKα radiation (λ = 0.71073 Å). The structure was solved by direct methods using SHELXT-2014 (Sheldrick, 2015a) and refined by full matrix least squares with SHELXL-2014 (Sheldrick, 2015b), refining on F2. Selected bonds and angles are given in Table 1. Detailed crystal data and structure refinement are listed in Table 4. Crystallographic data has been deposited with the Cambridge Crystallographic Centre as supplementary publication number CCDC-2052415.
Crystal data and refinement parameters
| Empirical formula | C21H15N3O6Pb |
| Formula weight | 612.56 |
| Crystal dimensions (mm) | 0.20 × 0.22 × 0.25 |
| Crystal system | Monoclinic |
| Space group | P21/n |
| a (Å) | 10.6490(5) |
| b (Å) | 13.9872(6) |
| c (Å) | 13.6435(6) |
| α (°) | 90.00 |
| β (°) | 106.422(5) |
| γ (°) | 90.00 |
| V (Å3) | 1949.29(16) |
| Z | 4 |
| Dc (g·cm−3) | 2.807 |
| μ (mm−1) | 8.702 |
| F (000) | 1168 |
| T (K) | 145(1) |
| λ (Å) | MoKα (0.71073) |
| θ Range (°) | 3.4–25.0 |
| Measured reflections | 9501 |
| Unique reflections | 3444 |
| Observed reflections | 2991 |
| No. of parameters refined | 281 |
| R1, WR2 [I>2σ(I)] | 0.0326, 0.0634 |
| R1, WR2 [all data] | 0.0398, 0.0667 |
| GOOF | 1.020 |
| Largest peak and hole (e·Å−3) | 1.18, −1.55 |
Funding information:
Natural Science Foundation of Shandong Province (ZR2014BL006 and ZR2015BL003), A Project of Shandong Province Higher Educational Science and Technology Program (J14LC19), and the funds of publicly funded domestic visiting program of Weifang Medical University have supported the work.
Author contributions:
Lu-Lin Zhang: experimental design, complex preparation, data collection, data interpretation, and writing. Shi-Li Tang: complex preparation, data collection, data interpretation, and writing. De-Jun Li: complex preparation, data collection, and writing. Yuan-Zheng Cheng: conceptualization, data interpretation, writing, funding acquisition, and supervision. Li-Ping Zhang: conceptualization, data interpretation, writing, funding acquisition, and supervision.
Conflict of interest:
The authors declared that they had no conflicts of interests in their authorship and publication of this contribution.
References
Alizadeh R., Amani V., Two new lead(II) coordination polymer and discrete complex containing bipyridine ligands with different positioned methyl substituents: synthesis, characterization, crystal structure determination, and luminescent properties. Struct. Chem., 2011, 22(5), 1153–1163.10.1007/s11224-011-9809-9Search in Google Scholar
Balch A.L., Oram D.E., Low-Coordinate Lead(II) Complexes with PbP2C and PbP4 Coordination. Preparations and Structures of Pb[(Ph2P)2CH]2 and Pb[(Ph2P)2C(SiMe3)]2. Inorg. Chem., 1987, 26(12), 1906–1912.10.1021/ic00259a020Search in Google Scholar
Bondi A., van der Waals Volumes and Radii. J. Phys. Chem., 1964, 68(3), 441–451.10.1021/j100785a001Search in Google Scholar
Catalano J., Murphy A., Yao Y., Yap G.P.A., Zumbulyadis N., Centeno S.A., et al., Coordination geometry of lead carboxylates – spectroscopic and crystallographic evidence. Dalton Trans., 2015, 44(5), 2340–2347.10.1039/C4DT03075CSearch in Google Scholar PubMed
Chen L., Yan C., Pan M., Fan Y.-Z., Zhang L.-Y., Yin S.-Y., et al., Semidirected versus holodirected coordination and single-component white light luminescence in Pb(II) complexes. New J. Chem., 2015, 39(7), 5287–5292.10.1039/C5NJ00720HSearch in Google Scholar
Cheng Y.-Z., Tang Y., Zhang L.-P., Syntheses, structures, and characterizations of two new lead(II) supramolecular complexes containing 4-aminobenzenesulfonate ligand. Main Group Chem., 2014a, 13(4), 293–306.10.3233/MGC-140142Search in Google Scholar
Cheng Y.-Z., Tang Y., Yan F., Synthesis and crystal structure of Pb(II) complex with 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone. Main Group Met. Chem., 2014b, 37(3–4), 101–106.10.1515/mgmc-2014-0005Search in Google Scholar
Ding B., Yang E.-C., Guo J.-H., Zhao X.-J., Wang X.-G., A novel 2D luminescent lead(II) framework with 3-carboxylic acid-4H-1,2,4-triazole based on binuclear Pb2Cl2(H2O)2 building blocks. Inorg. Chem. Commun., 2008, 11(12), 1481–1483.10.1016/j.inoche.2008.10.012Search in Google Scholar
Du Z.-Y., Ying S.-M., Mao J.-G., Two new lead(II) diphosphonates with second ligands as an intercalated species or a multidentate metal linker. J. Mol. Struct., 2006, 788(1–3), 218–223.10.1016/j.molstruc.2005.12.004Search in Google Scholar
Erxleben A., Interactions of copper complexes with nucleic acids. Coordin. Chem. Rev., 2018, 360, 92–121.10.1016/j.ccr.2018.01.008Search in Google Scholar
Fan S.-R., Zhu L.-G., Influence of the Reaction Conditions on the Self-assembly of Lead(II) 5-Sulfosalicylate Coordination Polymers with Chelating Amine Ligands. Inorg. Chem., 2006, 45(19), 7935–7942.10.1021/ic060871vSearch in Google Scholar
Huang G.-Z., Zou X., Zhu Z.-B., Deng Z.-P., Huo L.-H., Gao S., Effect of ligand configurations, secondary Pb–O interactions and auxiliary ligands on Pb(II)–mono/disulfonate complexes: syntheses, structures, and luminescence properties. CrystEngComm., 2017, 19(13), 1778–1791.10.1039/C7CE00071ESearch in Google Scholar
Janiak C., Temizdemir S., Scharmann T.G., Schmalstieg A., Demtschuk J., Hydrotris(1,2,4-triazolyl)borato Complexes with the Main Group Elements Ca, Sr, and Pb – Unexpectedly Bent ML2 Structures and a Stereochemically Inactive Lone Pair at Lead(II). Z. Anorg. Allg. Chem., 2000, 626(10), 2053–2062.10.1002/1521-3749(200010)626:10<2053::AID-ZAAC2053>3.0.CO;2-2Search in Google Scholar
Janiak C., A critical account on π-π stacking in metal complexes with aromatic nitrogen-containing ligands. J. Chem. Soc. Dalton Trans., 2000, 2000(21), 3885–3896.10.1039/b003010oSearch in Google Scholar
Jin J., Jia M.-J., Peng Y., Hou Q., Yu J.-H., Xu J.-Q., 4-Carboxylphthalhydrazidate-bridged layered Pb(II) coordination polymers. CrystEngComm., 2010, 12(6), 1850–1855.10.1039/b922767aSearch in Google Scholar
Jin F., Construction of a novel 2D Pb(II)-Organic framework: Syntheses, crystal structure, and property. J. Mol. Struct., 2020, 1217, 128373.10.1016/j.molstruc.2020.128373Search in Google Scholar
Kar P., Biswas R., Ida Y., Ishida T., Ghosh A., A Unique Example of Structural Diversity Tuned by Apparently Innocent o-, m-, and p-Nitro Substituents of Benzoate in Their Complexes of Mn(II) with 4,4’-Bipyridine: 1D Ladder, 2D Sheet, and 3D Framework. Cryst. Growth Des., 2011, 11(12), 5305–5315.10.1021/cg2008649Search in Google Scholar
Katz M.J., Michaelis V.K., Aguiar P.M., Yson R., Lu H., Kaluarachchi H., et al., Structural and Spectroscopic Impact of Tuning the Stereochemical Activity of the Lone Pair in Lead(II) Cyanoaurate Coordination Polymers via Ancillary Ligands. Inorg. Chem., 2008, 47(14), 6353–6363.10.1021/ic800425fSearch in Google Scholar
Kazak C., Arslan N.B., Karabulut S., Azaz A.D., Namlı H., Kurtaran R., Supramolecular lead(II) azide complex of 2,6-diacetylpyridine dihydrazone: synthesis, molecular structure, and biological activity. J. Coord. Chem., 2009, 62(18), 2966–2973.10.1080/00958970902980537Search in Google Scholar
Kowalik M., Masternak J., Kazimierczuk K., Kupcewicz B., Khavryuchenko O.V., Barszcz B., Exploring thiophene-2-acetate and thiophene-3-acetate binding modes towards the molecular and supramolecular structures and photoluminescence properties of Pb(II) polymers. CrystEngComm., 2020, 22(42), 7025–7035.10.1039/D0CE01224FSearch in Google Scholar
Lemercier G., Four M., Chevreux S., Two-photon absorption properties of 1,10-phenanthroline-based Ru(II) complexes and related functionalized nanoparticles for potential application in two-photon excitation photodynamic therapy and optical power limiting. Coordin. Chem. Rev., 2018, 368, 1–12.10.1016/j.ccr.2018.03.019Search in Google Scholar
Li S.-J., Liu J.-S., Guo J., Ji L.-L., Song W.-D., Ma D.-Y., Construction of two Novel 2D Coordination Frameworks with the Ligand H3nbtc: Synthesis, Crystal Structures, and Luminescence. Z. Anorg. Allg. Chem., 2012, 638(5), 832–837.10.1002/zaac.201100403Search in Google Scholar
Li J., A 2D Pb(II) coordination polymer based on 5-fluoronicotinic acid: Syntheses, structure and luminescence property. J. Mol. Struct., 2019, 1190, 160–164.10.1016/j.molstruc.2019.04.057Search in Google Scholar
Liu C.-B., Sun C.-Y., Jin L.-P., Lu S.-Z., Supramolecular architecture of new lanthanide coordination polymers of 2-aminoterephthalic acid and 1,10-phenanthroline. New. J. Chem., 2004, 28(8), 1019–1026.10.1039/b402803aSearch in Google Scholar
Lv L.-L., Xia W.-M., Cheng Y.-Z., Zhang L.-P., Wang X.-D., Synthesis, structure, DNA binding and anticancer activity of a new tetranuclear Pb(II) complex constructed by 8-hydroxyquinolinate and 4-nitrobenzoate ligands. Main Group Met. Chem., 2019, 42(1), 60–66.10.1515/mgmc-2019-0006Search in Google Scholar
Ma J.-x., Yang Z., Zhou T., Guo Q., Yang J., Yang T., et al., Construction of Structurally Diverse Luminescent Lead (II) Fluorinated Coordination Polymers Based on Auxiliary Ligands. New J. Chem., 2018, 42(18), 15413–15419.10.1039/C8NJ02846JSearch in Google Scholar
Mahjoub A.R., Morsali A., Direct synthesis of a dimeric mixed-anion lead(II) complex, crystal structure of [Pb(phen)(2OCCH3)(NCS)]2. Polyhedron, 2002, 21(12–13), 1223–1227.10.1016/S0277-5387(02)00977-4Search in Google Scholar
Meng F.-Y., Zhou Y.-L., Zou H.-H., Zeng M.-H., Liang H., Solution and solid-state photoluminescence of bis{succinatobis[2,6-bis(2-benzimidazolyl)] lead(II)}: A comment on the lone-pair stereochemistry and its effect on supramolecular interaction. J. Mol. Struct., 2009, 920(1–3), 238–241.10.1016/j.molstruc.2008.11.023Search in Google Scholar
Miao X.-H., Zhu L.-G., Influence of Secondary Bonds on the Network Assembly and Property in Lead(II) 3-Sulfobenzoate Coordination Polymer. Z. Anorg. Allg. Chem. 2008, 634(2), 335–338.10.1002/zaac.200700363Search in Google Scholar
Mirdya S., Frontera A., Chattopadhyay S., Formation of a tetranuclear supramolecule via non-covalent Pb⋯Cl tetrel bonding interaction in a hemidirected lead(II) complex with a nickel(II) containing metaloligand. CrystEngComm., 2019, 21(44), 6859–6868.10.1039/C9CE01283DSearch in Google Scholar
Mirdya S., Banerjee S., Chattopadhyay S., An insight into the non-covalent Pb⋯S and S⋯S interactions in the solid-state structure of a hemidirected lead(II) complex. CrystEngComm., 2020, 22(2), 237–247.10.1039/C9CE01548ESearch in Google Scholar
Mirtamizdoust B., Sonochemical synthesis of nano lead(II) metal-organic coordination polymer; New precursor for the preparation of nano-materials. Ultrason. Sonochem., 2017, 35, 263–269.10.1016/j.ultsonch.2016.10.001Search in Google Scholar PubMed
Morsali A., Mahjoub A.R., Darzi S.J., Soltanian M.J., Syntheses and Characterization of Mixed-Anions Lead(II) Complexes, [Pb(phen)2(CH3COO)]X (X = NCS−, NO3− and ClO4−), Crystal Structure of [Pb(phen)2(CH3COO)](ClO4). Z. Anorg. Allg. Chem., 2003, 629(14), 2596–2599.10.1002/zaac.200300154Search in Google Scholar
Najafi E., Amini M.M., Mohajerani E., Janghouri M., Razavi H., Khavasi H., Fabrication of an organic light-emitting diode (OLED) from a two-dimensional lead(II) coordination polymer. Inorg. Chim. Acta., 2013, 399, 119–125.10.1016/j.ica.2013.01.009Search in Google Scholar
Nugent J.W., Lee H.-S., Reibenspies J.H., Hancock R.D., Spectroscopic, structural, and thermodynamic aspects of the stereochemically active lone pair on lead(II): Structure of the lead(II) dota complex. Polyhedron, 2015, 91, 120–127.10.1016/j.poly.2015.02.033Search in Google Scholar
Pellissier A., Bretonnière Y., Chatterton N., Pécaut J., Delangle P., Mazzanti M., Relating Structural and Thermodynamic Effects of the Pb(II) Lone Pair: A New Picolinate Ligand Designed to Accommodate the Pb(II) Lone Pair Leads to High Stability and Selectivity. Inorg. Chem., 2007, 46(9), 3714–3725.10.1021/ic061823dSearch in Google Scholar PubMed
Ren H., Song T., Xu J., He X., Wang L., Zhang P., Self-assembly of two zinc(II) supramolecular architectures with carboxylate and chelating aromatic amine ligands: [Zn(nba)2(phen) (H2O)] and [Zn(nip)(phen)]n (nba = 4-nitrobenzoic acid, nip = 5-nitroisophthalic acid). Transit. Metal Chem., 2006, 31(8), 992–998.10.1007/s11243-006-0095-0Search in Google Scholar
Saha U., Dutta D., Bauzá A., Frontera A., Sarma B., Bhattacharyya M.K., Werner type clathrates involving guest benzoic acid and benzoate in discrete Mn(II) hosts: Experimental and theoretical studies. Polyhedron, 2019, 159, 387–399.10.1016/j.poly.2018.11.068Search in Google Scholar
Sahu J., Ahmad M., Bharadwaj P.K., Structural Diversity and Luminescence Properties of Coordination Polymers Built With a Rigid Linear Dicarboxylate and Zn(II)/Pb(II) Ion. Cryst. Growth Des., 2013, 13(6), 2618–2627.10.1021/cg400376gSearch in Google Scholar
Sammes P.G., Yahioglu G., 1,10-Phenanthroline: A Versatile Ligand. Chem. Soc. Rev., 1994, 23(5), 327–334.10.1039/cs9942300327Search in Google Scholar
Sarma R., Baruah J.B., Transformation of mixed anionic coordination polymers of lead. Inorg. Chim. Acta., 2009, 362(6), 1681–1686.10.1016/j.ica.2008.07.018Search in Google Scholar
Sheldrick G.M., SHELXT – Integrated space-group and crystal-structure determination. Acta Cryst., 2015a, A71, 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central
Sheldrick G.M., Crystal structure refinement with SHELXL. Acta Cryst., 2015b, C71, 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central
Shimoni-Livny L., Glusker J.P., Bock C.W., Lone Pair Functionality in Divalent Lead Compounds. Inorg. Chem., 1998, 37(8), 1853–1867.10.1021/ic970909rSearch in Google Scholar
Singh H.L., Singh J.B., Bhanuka S., Synthesis, spectral, DFT, and antimicrobial studies of tin(II) and lead(II) complexes with semicarbazone and thiosemicarbazones derived from (2-hydroxyphenyl)(pyrrolidin-1-yl)methanone, J. Coord. Chem., 2016, 69(2), 343–353.10.1080/00958972.2015.1115485Search in Google Scholar
Song J.-F., Yao R.-C., Qiu X.-M., Zhang X.-Y., Su L.-J., Zhou R.-S., Temperature-induced construction of two novel metal-organic frameworks with Pb-O-Pb inorganic skeletons and fluorescent properties. Inorg. Chem. Commun., 2018, 97, 25–29.10.1016/j.inoche.2018.09.002Search in Google Scholar
Srinivasan B.R., Shetgaonkar S.Y., Näther C., Bensch W., Solid state synthesis and characterization of a triple chain calcium(II) coordination polymer showing two different bridging 4-nitrobenzoate coordination modes. Polyhedron, 2009, 28(3), 534–540.10.1016/j.poly.2008.11.022Search in Google Scholar
Tsaryuk V., Kudryashova V., Gawryszewska P., Szostak R., Vologzhanina A., Zhuravlev K., et al., Structures, luminescence and vibrational spectroscopy of europium and terbium nitro- and dinitro-substituted benzoates. Nitro groups as quenchers of Ln3+ luminescence. J. Photoch. Photobio. A, 2012, 239, 37–46.10.1016/j.jphotochem.2012.04.022Search in Google Scholar
Wan Y., Zhang L., Jin L., Gao S., Lu S., High-Dimensional Architectures from the Self-Assembly of Lanthanide Ions with Benzenedicarboxylates and 1,10-Phenanthroline. Inorg. Chem., 2003, 42(16), 4985–4994.10.1021/ic034258cSearch in Google Scholar PubMed
Wang L., Roşca S.-C., Poirier V., Sinbandhit S., Dorcet V., Roisnel T., et al., Stable divalent germanium, tin and lead amino-(ether)-phenolate monomeric complexes: structural features, inclusion heterobimetallic complexes, and ROP catalysis. Dalton Trans., 2014, 43(11), 4268–4286.10.1039/C3DT51681DSearch in Google Scholar PubMed
Xiong K., Jiang F., Yang M., Wu M., Feng R., Xu W., et al., 2D Sheet-like architectures constructed from main-group metal ions, 4,4’-bpno and 1,2-alternate p-sulfonatothiacalix[4]arene. Dalton Trans., 2012, 41(2), 540–545.10.1039/C1DT11239BSearch in Google Scholar PubMed
Xu X.-J., Wu X.-Y., Xu W.-Z., Zhou W., Yan Y.-S., Hydrothermal Synthesis, Crystal Structure and Thermal Stability of a Supramolecular Lead(II) Complex with 4-Nitrobenzoic Acid and 1,10-Phenanthroline. Chinese J. Struct. Chem., 2012, 31(5), 639–644.Search in Google Scholar
Yang D., Guo J., Wu H., Ding Y., Zheng W., Synthesis and structural characterization of two-coordinate low-valent 14-group metal complexes bearing bulky bis(amido)silane ligands. Dalton Trans., 2012, 41(7), 2187–2194.10.1039/c1dt11774bSearch in Google Scholar PubMed
Yang L., Li Y., You A., Jiang J., Zou X.-Z., Chen J.-W., et al., Zinc(II) and lead(II) metal-organic networks driven by a multifunctional pyridine-carboxylate building block: Hydrothermal synthesis, structural and topological features, and luminescence properties. J. Mol. Struct., 2016, 1120, 327–332.10.1016/j.molstruc.2016.05.013Search in Google Scholar
Zhang X., Cheng J., Chen F., Sun M., Yao Y., Isomeric photoluminescent lead(II) coordination polymers based on designed pyridinecarboxylate ligands. Inorg. Chem. Commun., 2011, 14(2), 358–361.10.1016/j.inoche.2010.11.032Search in Google Scholar
Zhao L.-N., Chen L., Liu B., Li X.-M., Wang Q.-W., Hydrothermal Synthesis and Crystal Structure of Two Three-Dimensional Supramolecular Lead(II) Coordination Polymers. Chinese J. Inorg. Chem., 2013, 29(6), 1243–1248.Search in Google Scholar
Zhao Y.-H., Xu H.-B., Shao K.-Z., Xing Y., Su Z.-M., Ma J.-F., Syntheses, Characterization, and Luminescent Properties of Three 3D Lead-Organic Frameworks with 1D Channels. Cryst. Growth Des., 2007, 7(3), 513–520.10.1021/cg060535pSearch in Google Scholar
Zhu Y., Luo F., Song Y.-M., Huang H.-X., Sun G.-M., Tian X.-Z., et al., A series of 1D Dy(III) compound showing slow magnetic relaxation: synthesis, structure, and magnetic studies. Dalton Trans., 2012, 41(22), 6749–6755.10.1039/c2dt12313dSearch in Google Scholar PubMed
© 2021 Lu-Lin Zhang et al., published by De Gruyter
This work is licensed under the Creative Commons Attribution 4.0 International License.
