Article pubs.acs.org/crystal
Significant Proton Conductivity Enhancement through Rapid WaterInduced Structural Transformation from a Cationic Framework to a Water-Rich Neutral Chain Zhuanling Bai,†,‡,§ Yanlong Wang,†,‡,§ Wei Liu,†,‡ Yuxiang Li,†,‡ Jian Xie,†,‡ Lanhua Chen,†,‡ Daopeng Sheng,†,‡ Juan Diwu,†,‡ Zhifang Chai,†,‡ and Shuao Wang*,†,‡ †
School for Radiological and Interdisciplinary Sciences (RAD-X), Soochow University, Jiangsu 215123, China Collaborative Innovation Center of Radiation Medicine of Jiangsu Higher Education Institutions, Jiangsu 215123, China
‡
S Supporting Information *
ABSTRACT: Searching for new host materials tailored for the high proton conductivity is highly desirable for the new generation of fuel cell system. We report here an anionexchangeable cationic metal organic framework with the formula of [Ce(Ccbp)2]Br0.25Cl0.75·6H2O·2DMF (compound 1), which is constructed through the self-assembly of zwitterionic-based ligands H 2CcbpBr (H2CcbpBr = 4carboxy-1-(4-carboxybenzyl)pyridinium bromide) and (NH4)2Ce(NO3)6. During the investigation of humiditydependent proton conduction behavior, we observed a rare case of rapid water-induced single-crystal-to-single-crystal phase transformation from compound 1 to a neutral chain [Ce(Ccbp)3(H2O)3]·8H2O (compound 2). This structural transformation originates from the coordination of water to Ce(III) metal centers, distortion of ligands, and the soft nature of the cationic framework 1, as probed and confirmed by a variety of investigations including color change, water vapor adsorption measurement, powder X-ray diffraction, single-crystal X-ray diffraction, humidity-dependent proton-conducting measurements, IR and UV−vis spectroscopies, and thermogravimetric analysis. As a consequence, this process introduces significant amounts of both coordinated and lattice water molecules into the structure, further giving rise to a decent water-assisted proton conductivity of 1.104 × 10−4 S cm−1 at 368 K and 95% relative humidity.
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nels.20−22 Although their practical applications are still limited currently, the emergence of proton-conducting MOFs shed light on a better understanding of the proton transportation pathways and mechanisms at the molecular level based on their comprehensive structural information. Proton-conducting MOFs can generally be divided into two categories. The majority consists of water-assisted proton-conducting MOFs that can only be operated in a water-mediated environment below 373 K.23−26 In this case, water molecules play a key role in the process of proton conduction for water-mediated protonconducting MOFs by contributing to the hydrogen-bonding network and acting as direct proton carriers. The other category contains only a handful of cases, which can be operated under anhydrous conditions in the intermediate temperature range of 373−573 K.27,28 This class of materials often involves dehydration or phase transition processes at relatively high temperatures, where protons are partially activated. A recent example shows that a crystalline coordination polymer containing an extremely dense and thermally stable hydrogen
INTRODUCTION Metal−organic frameworks (MOFs) have extensively been explored during the last two decades owing to not only their advantageous features in terms of high surface area, intriguing and uniform architecture but also their tunable and flexible pore size and corresponding diversity as a result of versatile coordination mode of metal centers and abundant selections of bridging ligands.1−4 Single-crystal-to-single-crystal phase (SC-SC) transformations have been reported for many flexible MOFs, which allows for direct visualization of the structural transition and, therefore, the underlying transformation mechanism through single-crystal X-ray diffraction,5−9 leading to change and tuning of physical and chemical properties including color, stability, luminescence, magnetism, gas adsorption, ion-exchange capability, catalytic activity, ionic conductivity, etc.10−14 In general, phase transformation of MOFs includes changes in geometry and coordination number, interpenetration, framework distortion, and structural dimensionality,15−18 whereas combined changes in the packing arrays and overall net charge of the framework are relatively scarce.19 On the other hand, MOFs have been explored as new platforms for proton conduction due to their defined frameworks with chemically adjustable porosities/chan© 2017 American Chemical Society
Received: March 31, 2017 Revised: May 3, 2017 Published: May 15, 2017 3847
DOI: 10.1021/acs.cgd.7b00469 Cryst. Growth Des. 2017, 17, 3847−3853
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reduced pressure to give a white power, which was recrystallized in H2O to afford colorless crystals. Synthesis of Compound 1. Compound 1 was synthesized by solvothermal reaction. A reactant mixture of H2CcbpBr (25.8 mg, 0.1 mmol), Ce(NH4)2(NO3)6 (54.8 mg, 0.1 mmol), DMF (4 mL), and H2O (1 mL) was loaded into a 20 mL glass vial and heated at 100 °C for 5 h, followed by slow cooling to room temperature. The product was obtained as dark yellow block-shaped crystals (yield: 67% based on cerium), recovered by filtration, and subsequently washed with DMF and ethanol. Yield: ca. 55.3% (based on Ce(NH4)2(NO3)6). Anal. Calcd for C34H56O16N4Cl0.75Br0.25Ce: C, 45.02%; H, 4.634%; N, 6.17%; Found: C, 44.15%; H, 4.208%; N, 5.947%. Powder X-ray diffraction (PXRD) analysis was conducted to verify the purity of compound 1 (Figure S1). N2 and Water Vapor Adsorption Measurements. Measurements were carried out using a Quantachrome Autosorb Gas Sorption analyzer IQ2. The samples of compound 1 were soaked into a methanol solution of LiCl, and the solutions were refreshed every 6 h for 3 days. Similarly, the samples were further treated with methanol to remove the excess LiCl in the solvent (soaked in methanol for 3 d and fresh methanol was added every 8 h). After decanting the methanol extract, the samples were dried under a dynamic vacuum ( 2σ(I))a,b R1, ωR2 (all data)a,b
C28H20CeN2O8 652.58 monoclinic C2/c 20.0073(10) 20.9035(10) 8.9515(4) 90 113.186(3) 90 3441.3(3) 4 1.260 1.364 1464 293(2) 1.000 0.0227, 0.0639 0.0273, 0.0656
C30H29N3O10Ce 784.36 hexagonal P63 15.9104(14) 15.9104(14) 14.7913(12) 90 90 120 3242.6(6) 2 1.104 0.764 1080 293(2) 1.086 0.0644, 0.1719 0.1037, 0.1926
R1 = ∑||Fc| − |Fc|/∑|Fo|. bωR2 = [∑{ω(Fo2 − Fc2)2/∑ω(Fo2)2}1/2.
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RESULTS AND DISCUSSION Single-crystal X-ray diffraction analysis reveals that compound 1 crystallizes in the triclinic space group of C2/c and features a 3D framework composed of the metal chains of the cerium− carboxylate subunit. As shown in Figure 1a, the asymmetric unit of compound 1 consists of half of a cerium(III) ion and one ligand (Ccbp−). Each cerium(III) cation is eight-coordinate, displaying a dodecahedron geometry with eight oxygens from eight different carboxylate groups of ligands. The overall coordination geometry of Ce(III) ion may be described as a standard D4d square antiprism.50 Each carboxylate group from
Figure 1. (a) The asymmetric unit of compound 1. (b) Metal− carboxylate chain in compound 1. (c) Torsion angle of the Ccbp ligand. (d) Three-dimensional framework structure of compound 1. 3849
DOI: 10.1021/acs.cgd.7b00469 Cryst. Growth Des. 2017, 17, 3847−3853
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Figure 2. Nyquist plots of compound 1 at 40−90% RH and 90 °C.
Figure 4. The color change of compounds 1 and 2 and the corresponding absorption spectra.
Figure 5. (a) The asymmetric unit of compound 2. (b) Torsion angle of the Ccbp of compound 2. (c) One-dimensional structure of compound 2. Figure 3. PXRD of compound 1 after proton-conducting measurement and simulated patterns of compounds 1 and 2.
geometry can be best described as a 9-coordinate monocapped square antiprism. Every two adjacent Ce(III) ions are bridged by three Ccbp ligands through six terminal carboxylate groups in a monodentate coordination mode (Figure 5a). Conformational versatility is a common phenomenon for flexible ligands. Figure 5b shows that the N−C−C torsion angles of the Ccbp are 107.998° (nearly close to 109°) which contrast sharply with those of compound 1, suggesting the stability of compound 2 would be elevated. This is confirmed by the fact that the structure of compound 2 remains intact in water. The possible process of phase transition is depicted in Figure 6. We propose that water molecules can move rapidly into the channels of compound 1, attacking the Ce(III) sites of high hydrophilicity, forming Ce−Ow bonds. The framework structure soon rearranges drove by intrinsic instability origin that the torsion angles of the Ccbp significantly deviate from the standard value. The unbound halide anions are further substituted by the bridging Ccbp− ligand, leading to a transformation of a cationic 3D framework into a neutral chain with a noticeably increased amount of both coordinated and lattice water molecules. This process would involve partial releasing of Ce(III) halide salts back into the aqueous solution. Thermogravimetric measurements were carried out under a nitrogen atmosphere with a heating rate of 10 °C min−1. As illustrated in the Figure 7, compounds 1 and 2 are thermally stable up to ca. 260 °C. For compound 1, the first weight loss of 4.6% in the range of 30−120 °C was assigned to the removal of guest molecules DMF and water, followed by the framework
is present), which also hints for the occurrence of phase transformation after contacting with water. To complete the transformation from compound 1 to compound 2, a dry sample of compound 1 was soaked into water. Interestingly, the color of the sample instantly changed from dark yellow to light yellow with the contact of water (Figure 4). In addition to the color mutation, this transformation can be also probed by the discrepant absorption spectra of the solids of two compounds. As shown in Figure 4, the UV−vis absorption spectra of the compound 1, compound 2, and ligand all display intense absorption bands in the highenergy region (λ < 300 nm) associated with the π → π* transition of the ligand, while compounds 1 and 2 exhibit low energy bands in the range of 300−500 nm, which may be assigned as the charge transfer between the Ce3+ and Ccbp ligand. The characteristic peak intensity reduction corresponds to the color change from compound 1 to compound 2.57−60 We further performed single-crystal X-ray diffraction analysis on compound 2 to further understand the transformation mechanism. The result reveals that compound 2 crystallizes in the hexagonal space group P63 and contains a series of 1D neutral chains. The triple-stranded chains consist of a central Ce(III) center coordinated by nine oxygen atoms from six Ccbp ligands and three water molecules. The Ce center sits on the 3-fold axis (Figure 5a), and its overall local coordination 3850
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that proton conductivity is almost directly proportional to the water content with no sudden change (shown in Figure 9b).
Figure 8. Nyquist plots of (a) compound 2 at 30−40 °C and 90% RH, (b) compound 2 at 50−70 °C and 90% RH, and (c) compound 2 at 80−90 °C and 90% RH. (d) Arrhenius plot of the temperature dependence of conductivity at 90% RH for compound 2.
Figure 6. Diagram showing the possible process of phase transition from compound 1 to compound 2.
Figure 9. Proton conductivities of (a) compound 1 and (b) compound 2 at 30−90% RH at 90 °C.
The proton conductivities of compound 2 at low humidity 30% RH and 40% RH are both higher than those of compound 1, at 1.736 × 10−5 and 2.514× 10−5 S cm−1, respectively. In addition, there is no obvious difference for the proton-conducting behavior at a humidity higher than 50% RH with that of compound 2 (Figure S6). These observations further affirmed the process of phase transition. Furthermore, an increase in conductivity with increasing temperature was observed at 90% RH, as shown in the Figure 8. The highest conductivity was 1.104 × 10−4 S cm−1 at 90 °C and 90% RH. As shown in Figure 8d, the conductivity of compound 2 was found to follow the linear relationship with temperature in the Arrhenius plot. The activation energy (Ea) of this conductivity was calculated to be 0.6 eV (>0.4 eV), which indicates the vehicular mechanism.23−28,53−55
Figure 7. Thermogravimetric analysis of compounds 1 and 2.
decomposition. Weight losses of compound 2 can be divided into three distinct stages. The first stage from 30 to 100 °C corresponds to the loss of volatilization of physically adsorbed water and residual solvent in the void space. In the second stage (100−260 °C), the weight loss is clearly an elevation compared to that of compound 1 owing to the existence of coordinated water molecules. The third stage (>260 °C) suggests the destruction of the basic skeleton of compound 2. FT-IR analysis was further carried out to verify the singlecrystal-to-single-crystal transformation. Figure S2 illustrates that two compounds contain almost identical broad features in the range from 500 to 2500 cm−1. The broad peak located at 3390−3450 cm−1, attributed to the vibrations of the water molecules, indicates the presence of lattice and coordinated water molecules. This feature in compound 2 is stronger than that in compound 1, consistent with fact of water anticipation during the phase transition. Finally, to assess the proton conductivity after complete phase transition, ac impedance analysis was carried out directly on compound 2 at 90 °C and 30%−90% RH. The results show
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CONCLUSIONS In conclusion, we have demonstrated an unusual case of waterinduced single-crystal-to-single-crystal phase transformation from a 3D porous cationic MOF compound 1 to a 1D neutral chain structure compound 2. This process was originally probed by the humidity-dependent proton-conducting measurements and further confirmed by combined color change, powder X-ray diffraction, single-crystal X-ray diffraction, IR and UV−vis spectroscopies, and thermogravimetric analysis. This type of phase transition is not typical for a lanthanide-based 3851
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MOF system given that most of the lanthanide-based MOFs are hydrolytically stable. It allows for introducing large amounts of water content into the structure, providing a new method to enhance the proton conductivity in flexible MOFs materials.
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ASSOCIATED CONTENT
S Supporting Information *
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.cgd.7b00469. Experimental methods, PXRD, SEM-EDX, IR-spectra, anion-exchange kinetic curves, and ac impedance analysis (PDF) Accession Codes
CCDC 1541541−1541542 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing
[email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
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AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. ORCID
Shuao Wang: 0000-0002-1526-1102 Author Contributions §
These authors contributed equally.
Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS We are grateful for funding support from the National Science Foundation of China (21422704 and 21601131), the Science Foundation of Jiangsu Province (BK20140007, 16KJB150035, and 1501156B), the General Financial Grant from the China Postdoctoral Science Foundation (2016M590493), “Young Thousand Talented Program”, and a Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).
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