English

• 1. INTRODUCTION

  Crystal engineering of coordination polymers (CPs) has been a field of rapid growth in coordination and material chemistry not only because of their intriguing topologies but also for their interesting physical and chemical properties^[1-6], such as catalysis^{[7, 8]}, gas storage/adsorption^[9-11], separations^[12-15], drug delivery^{[16, 17]} and so on. Coordination polymers are polymeric, supramolecular assemblies of metal ions (or metal clusters) and organic ligands linked through coordination bonds. Though crystal engineering affords us powerful approaches for preparing CPs, it is still a long-term challenge to rationally design and synthesize CPs with desired properties^[18-20]. Hence, more and more scientists were attracted into this area and a large number of structures with potential applications were reported. However, among the reported CPs, silver(I) phosphonate based CPs are much less explored because of their sensitivity to light and tendency to yield highly insoluble polymers/oligomers^[21-25].

  As is well known, the flexibility of ligand plays a very important role in the construction of CPs because the shape, symmetry and length of a ligand can be affected by its flexibility. Rigid ligands have the benefit to construct CPs with expected structures. However, it is not easy to predict the structures of CPs constructed from flexible ligands mainly because flexible ligands can adopt a variety of conformations in coordination process especially by the affection of central metal ions. A large number of interesting CPs incorporating flexible ligands with metal ions has already been obtained. Taking account of the above, we select a flexible ligand, 1, 3-bis(diphenyphosphino)propane (DPPP), which contains four rigid benzene ring pieces and one flexible propyl chain. On the other hand, DPPP has strong coordination affinities to Ag(I) because phosphine belongs to soft base and Ag(I) belongs to soft acid according to the soft and hard acid-base theory in coordination chemistry^[26]. To the best of our knowledge, the Ag(I)-based CPs assembled with PhPO₃H₂ and DPPP ligands have not been found in the literature. In this work, the solvothermal reactions of CF₃COOAg with PhPO₃H₂ and DPPP in mixed organic solvent at 65 ℃ gave rise to a new Ag(I)-based CP, namely [Ag₂(PhPO₃H)₂-(DPPP)]_n (1). Additionally, the thermal stability and photoluminescent property of 1 were also investigated.

  2. EXPERIMENTAL

  2.1 Materials and general methods

  All starting reagents were of AR grade and used as received without further purification. The crystal data were collected on a Bruker Apex II CCD diffractometer. IR spectrum was recorded with KBr pellets on a Tensor 27 OPUS (Bruker) FT-IR spectrometer in the 4000~400 cm^–1 range. Analyses of C, H and P were determined on a Perkin-Elmer 240 Elemental analyzer. The powder X-ray diffraction patterns (PXRD) were conducted at 40 kV and 100 mA on a Rigaku D/Max-2500 diffractometer, using a graphite-monochromator and a Cu-target tube under ambient conditions. Thermogravimetric analysis (TGA) experiments were recorded at a heating rate of 10 ℃/min from 40 to 800 ℃ on a NETZSCH STA 449F3 thermal analyzer under N₂. The solid UV-Vis spectra were measured on a UV25500 UV-VIS-NIR Spectrophotometer (Shimadzu Corp.). The luminescence excitation/emission spectra were measured at room temperature on a Hitachi F-4600 fluorescence spectrophotometer.

  2.2 Synthesis of [Ag₂(PhPO₃H)₂(DPPP)]_n (1)

  A mixture of CF₃COOAg (90 mg, 0.41 mmol), PhPO₃H₂ (16 mg, 0.1 mmol), DPPP (41 mg, 0.1 mmol), MeCN (2 mL), CH₃OH (2 mL), DMF (2 mL) and H₂O₂ (30%, 100 uL) was sealed in a Teflon-lined stainless-vessel (15 mL) and heated at 65 ℃ for 24 hours, then cooled to room temperature at a rate of 5 ℃·h⁻¹. The colorless blocks of 1 were collected and washed thoroughly with MeCN and dried in air. Yield: 43 mg (46%, based on PhPO₃H₂). Analysis calculated for C₃₉H₃₈Ag₂O₆P₄ (%): C, 49.71; H, 4.06; P, 13.15. Found (%): C, 49.67; H, 3.97; P, 13.22. IR (KBr, cm^–1): 3436(m), 3049(w), 2902(w), 2700(w), 1630(m), 1477(w), 1432(s), 1392(w), 1232(m), 1130(s), 1051(s), 908(s).

  2.3 Crystallographic measurements and structure determination

  Suitable single crystal of 1 for X-ray diffraction was obtained directly from the above experiment. Crystallographic data of 1 were collected at room temperature on a Bruker Apex-II CCD area detector by using graphite-monochro-matized MoKα (λ = 0.071073 nm). The crystal was mounted on a glass fiber. The structure was solved by direct methods^[27] and refined by full-matrix least-squares on F² using the SHELXTL-2014^[28]. All non-hydrogen atoms were refined by full-matrix least-squares techniques with anisotropic displacement parameters and the hydrogen atoms were geometrically fixed at the calculated positions attached to their parent atoms, and treated as riding atoms. Crystal data for 1: triclinic system, space group P$ \overline 1 $ with a = 9.9472(4), b = 12.7505(5), c = 12.7505(5) Å, V = 1896.22(14) ų, Z = 2, C₃₉H₃₈Ag₂O₆P₄, M_r = 942.31, D_c = 1.764 g/cm³, F(000) = 1012, GOOF = 1.135, the final R = 0.0412, wR = 0.1415 (w = 1/[σ²(F_o²) + (0.0720P)² + 4.06P], where P = (F_o² + 2F_c²)/3), (Δ/σ)_max = 0.001, (Δρ)_max = 1.070 and (Δρ)_min = –0.684 e/ų. The selected bond lengths and bond angles and the hydrogen bond information for 1 are given in Tables 1 and 2, respectively.

  Table 1

  

  Table 1.  Selected Bond Lengths (Å) and Bond Angles (º) for 1

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  Bond	Dist.		Bond	Dist.
  Ag(1)–O(4)	2.320(3)		Ag(2)–O(2B)	2.244(3)
  Ag(1)–P(2)	2.3622(10)		P(4)–O(5)	1.508(4)
  Ag(1)–O(4A)	2.274(3)		P(4)–O(4)	1.514(3)
  Ag(2)–O(3)	2.314(3)		P(4)–O(6)	1.564(3)
  Ag(2)–P(1)	2.3738(11)
  Angle	(°)		Angle	(°)
  O(4A)–Ag(1)–O(4)	73.04(12)		P(3)–O(3)–Ag(2)	123.88(17)
  O(4A)–Ag(1)–P(2)	142.02(9)		P(3)–O(2)–Ag(2B)	146.4(3)
  O(4)–Ag(1)–P(2)	143.94(8)		P(4)–O(4)–Ag(1A)	129.6(2)
  O(2B)–Ag(2)–O(3)	110.79(14)		P(4)–O(4)–Ag(1)	121.94(17)
  O(2B)–Ag(2)–P(1)	118.44(11)		Ag(1A)–O(4)–Ag(1)	106.96(12)
  O(3)–Ag(2)–P(1)	125.24(8)
  Symmetry codes: A –x, –y + 1, –z; B –x, –y +1, –z + 1

  3. RESULTS AND DISCUSSION

  3.1 Description of the crystal structure

  Complex 1 crystallizes in triclinic system, space group P$ \overline 1 $. As shown in Fig. 1, its asymmetric unit contains two Ag atoms, two PhPO₃H^– ligands and one DPPP ligand. Two kinds of rings are found in 1, such as the four-membered ring with Ag₂O₂ (Fig. 2 i) and the eight-membered ring with Ag₂O₄P₂ (Fig. 2 ii) constructed by PhPO₃H^– ligands, which were then connected by DPPP ligands forming a zigzag type chain (Fig. 2 iii). The distance of Ag(1) and Ag(1A) in the four-membered ring is 3.6922 Å, whereas that of Ag(2) and Ag(2B) in the eight-membered ring is 4.7531 Å. The coordination geometry of each Ag(I) ion locates in a planar trigonal mode. The coordinated atoms for each Ag(I) ion are two oxygen atoms and one phosphorus atom. The average bond length of Ag(1)–O(4) and Ag(1)–O(4A) is 2.297 Å, while that of Ag(2)–O(3) and Ag(2)–O(2B) is 2.279 Å. The band lengths of Ag(1)–P(2) and Ag(2)–P(1) are 2.3622 and 2.3738, respectively. The angles of O(4)–Ag(1)–O(4A) and O(3)–Ag(2)–O(2B) are 73.04° and 110.79°, respectively. No classical hydrogen bond was observed among the chains in the packing crystal structure.

  Figure 1

  

  Figure 1.  Asymmetric unit in complex 1. All H atoms are omitted for clarity (except H atoms on the O atoms)

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  Figure 2

  

  Figure 2.  Four-membered ring with Ag₂O₂ (i), eight-membered ring with Ag₂O₄P₂ (ii) and the zigzag type chain (iii) in complex 1. All H atoms are omitted for clarity (except H atoms on the O atoms)

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  3.2 IR spectrum

  The absorption at 3436 cm^–1 can be attributed to the stretching vibration of O–H bond of groups -PO₃H^[29]. The peak at 3049 cm^–1 should be assigned to the stretching vibrations of the C–H bonds of benzenes. The strong absorption at 1200~900 cm^–1 is the typical stretching vibration of -PO₃. The peaks of 1130 and 1051 correspond to the asymmetric and symmetric stretching vibration of PO₂ respectively, whereas the peak at 908 cm^–1 can be ascribed to the stretching vibration of P–OH bond^[30], indicating the existence of -PO₃H groups in complex 1.

  3.3 Powder X-ray diffraction (PXRD) and thermal stability

  The powder X-ray diffraction of complex 1 was also performed at room temperature. The pattern calculated from single-crystal X-ray data of 1 was in good agreement with the observed ones in almost identical peak positions (Fig. 3), which confirmed the pure phase of 1. The different reflection intensity between the simulated and experimental patterns could be ascribed to the powder size and variation in preferred orientation for the powder samples during the collection of experimental PXRD data.

  Figure 3

  

  Figure 3.  Simulated and experimental PXRD patterns for complex 1

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  To study the thermal stability of complex 1, thermogravimetric analysis (TGA) was performed (Fig. 4). The TGA curve exhibits compound 1 shows good thermal stability under 280 ℃. One obvious weight loss step was observed from 280 to 500 ℃ with the weight loss of about 70.96%, which is equivalent to the release of organic ligands (calcd.: 70.39%). Finally, the residue remains about 28.91% according to the produced compound of silver phosphate (calcd.: 29.53%).

  Figure 4

  

  Figure 4.  TGA curve of complex 1

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  3.4 Diffuse-reflectance UV-Vis spectra and photoluminescence properties

  The UV-Vis absorption spectra of DPPP, PhPO₃H₂ and complex 1 were recorded in the solid state at room temperature (Fig. 5). As shown in the absorption spectra of DPPP and PhPO₃H₂, both of them have two absorption peaks (260 and 295 nm for DPPP; 218 and 269 nm for PhPO₃H₂), which can mainly be ascribed to the B-band showing the characteristic absorption band of aromatic compounds, and the R-band showing the characteristic absorption band of the conjugated bond with heteroatom^[31], corresponding to the π → π^* and n → π^* transitions^{[32, 33]}. Accordingly, the absorption peaks for 1 (254 and 333 nm) are very similar to the free DPPP ligand, which should be mainly assigned as π → π^* or n → π^* transitions of DPPP ligand.

  Figure 5

  

  Figure 5.  Solid UV-Vis absorption spectra for DPPP, PhPO₃H₂ and complex 1 at room temperature

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  As shown in Fig. 6, the solid-state photoluminesent properties of DPPP and complex 1 have been investigated in the solid state at room temperature (The photoluminesent spectra of PhPO₃H₂ are not shown in Fig. 6 because of its very weak photoluminescent property). Complex 1 shows a main emission peak at 475 nm (λ_ex = 291 nm), whereas the main emission peak of DPPP is 459 nm (λ_ex = 260 nm). The emission characteristic of complex 1 is similar to that of the free DPPP ligand, which indicates that intraligand excitation is responsible for the emission of 1. Comparison of emission spectra of DPPP and complex 1 reveals that the emission peak of complex 1 exhibits a red-shift with 16 nm, which mainly originates from the ligand-to-metal charge transfer^[32].

  Figure 6

  

  Figure 6.  Emission spectra of DPPP ligand and complex 1 at room temperature

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  4. CONCLUSION

  In summary, we successfully synthesized a new Ag(I)-based CP 1 from the solvothermal reaction of CF₃COOAg with DPPP and PhPO₃H₂ ligands in mixed organic solvent at 65 ℃. A four-membered ring with Ag₂O₂ and an eight-membered ring with Ag₂O₄P₂ were observed in the structure of complex 1. Moreover, complex 1 shows good stability and photoluminescent property. This work may further enrich the family of Ag(I)-based coordination polymers.

  
  
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• 

  Figure 1  Asymmetric unit in complex 1. All H atoms are omitted for clarity (except H atoms on the O atoms)

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  Figure 2  Four-membered ring with Ag₂O₂ (i), eight-membered ring with Ag₂O₄P₂ (ii) and the zigzag type chain (iii) in complex 1. All H atoms are omitted for clarity (except H atoms on the O atoms)

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  Figure 3  Simulated and experimental PXRD patterns for complex 1

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  Figure 4  TGA curve of complex 1

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  Figure 5  Solid UV-Vis absorption spectra for DPPP, PhPO₃H₂ and complex 1 at room temperature

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  Figure 6  Emission spectra of DPPP ligand and complex 1 at room temperature

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  Table 1.  Selected Bond Lengths (Å) and Bond Angles (º) for 1

  Bond	Dist.		Bond	Dist.
  Ag(1)–O(4)	2.320(3)		Ag(2)–O(2B)	2.244(3)
  Ag(1)–P(2)	2.3622(10)		P(4)–O(5)	1.508(4)
  Ag(1)–O(4A)	2.274(3)		P(4)–O(4)	1.514(3)
  Ag(2)–O(3)	2.314(3)		P(4)–O(6)	1.564(3)
  Ag(2)–P(1)	2.3738(11)
  Angle	(°)		Angle	(°)
  O(4A)–Ag(1)–O(4)	73.04(12)		P(3)–O(3)–Ag(2)	123.88(17)
  O(4A)–Ag(1)–P(2)	142.02(9)		P(3)–O(2)–Ag(2B)	146.4(3)
  O(4)–Ag(1)–P(2)	143.94(8)		P(4)–O(4)–Ag(1A)	129.6(2)
  O(2B)–Ag(2)–O(3)	110.79(14)		P(4)–O(4)–Ag(1)	121.94(17)
  O(2B)–Ag(2)–P(1)	118.44(11)		Ag(1A)–O(4)–Ag(1)	106.96(12)
  O(3)–Ag(2)–P(1)	125.24(8)
  Symmetry codes: A –x, –y + 1, –z; B –x, –y +1, –z + 1

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•