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All Roads Lead to Rome: Tuning the Luminescence of a Breathing Catenated Zr-MOF by Programmable Multiplexing Pathways Cheng-Xia Chen, Zhang-Wen Wei, Chen-Chen Cao, Shao-Yun Yin, Qian-Feng Qiu, Neng-Xiu Zhu, Yang-Yang Xiong, Ji-Jun Jiang, Mei Pan, and Cheng-Yong Su Chem. Mater., Just Accepted Manuscript • DOI: 10.1021/acs.chemmater.9b01258 • Publication Date (Web): 22 Jul 2019 Downloaded from pubs.acs.org on July 23, 2019
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Experimental Materials and Instrumentation. All the reagents and solvents were purchased from commercial sources and directly utilized without further purification. Solid-state IR spectra were recorded using Nicolet/Nexus-670 FT-IR spectrometer in the region of 4000-400 cmL/ using KBr pellets. Single-crystal X-ray diffraction data were collected on a Rigaku Oxford SuperNova X-RAY diffractometer system equipped with a Cu sealed tube 6N = 1.54178 Å) at 50 kV and 0.80 mA. Powder X-ray diffraction (PXRD) was carried out with a Rigaku SmartLab diffractometer (Bragg-Brentano geometry, Cu KQ/ radiation, N = 1.54056 Å). Nuclear magnetic resonance (NMR) data were collected on a 400 MHz Nuclear Magnetic Resonance Spectrometer. Thermogravimetric (TG)-mass spectrum (MS) analyses were performed on a NETZSCH TG209 system in nitrogen and under 1 atm of pressure at a heating rate of 10 °C min-1. Gas adsorption isotherms for pressures in the range of 01.0 bar were obtained by a volumetric method using a Quantachrome Autosorb-iQ2-MP gas adsorption analyzer using ultra-high purity N2 gas. For pre-treatment, LIFM-114 was subsequently washed with DMF and immersed in anhydrous acetone for 3 days, during which the solvent was decanted and freshly replenished three times a day. The samples were activated under vacuum at 50 oC for 1.0 hour, and gas sorption measurements were then conducted. UV-Vis absorption spectra were recorded using a Shimadzu UV-2450 spectrophotometer. Fluorescence microscopy photos were taken by UV lamp using radiation of 365 nm. Fluorescence spectra were measured by Edinburgh FLS 980 spectrometer. The absolute quantum yields for fluorescence emission (400 to 800 nm) were measured on a Hamamatsu C9920-02G absolute PL quantum yield measurement system. Ligand Synthesis. 4', 4''', 4''''', 4'''''''-(ethene-1, 1, 2, 2tetrayl)tetrakis(([1, 1'-biphenyl]-4-carboxylic acid)) (H4ETTC) was synthesized according to a previously reported literature.26 MOF Synthesis and Transformation. Synthesis of LIFM114. H4ETTC (30 mg), ZrOCl2·8H2O (90 mg), DMF (9 mL) and HCOOH (6 mL) were charged in a vial. The mixture was ultrasounded for 10 min, and then was heated in a 120 oC oven for 24 h. After cooling down to room temperature, light green rod crystals of LIFM-114 were harvested (32.8 mg, 73.3 %). Transformation from LIFM-114 to LIFM-114cp. The assynthesized LIFM-114 was washed thoroughly with DMF (5 mL × 3), and then soaked in acetone for three days, during which the solvent was decanted and freshly replenished three times a day. Afterwards, the samples were dried at 50 oC for 1 h under vacuum. The yellow samples of LIFM-114cp (cp refers to close packing) were obtained. Or otherwisely, directly heating the prestine LIFM-114 sample at 100 oC for 15 minutes also results in LIFM-114cp. Transformation from LIFM-114cp to LIFM-114. Method I: 30 mg LIFM-114cp was added together with 200 L TFA into a 10 mL vial, after adding 4 mL DMF, the mixture was heated at 100 °C for 10 h. After being washed with DMF (10 × 2 mL) and acetone (5 × 2 mL), light green powder of LIFM-114 was recovered. Method II: 30 mg LIFM-114cp was added into a 20 mL vial, after adding 10 mL DMF, the mixture was heated at 100 °C for 20 h. After being washed with DMF (10 × 2 mL) and acetone (5 × 2 mL), light green powder of LIFM-114 was recovered.
Transformation of LIFM-114 into LIFM-114-S (S = dichloromethane (DCM), ethanol (EtOH), methanol (MeOH), ether (Et2O), or toluene, respectively). The pristine LIFM-114 was washed thoroughly with DMF (5 mL × 3), and then soaked in different organic solvent for three days, during which the solvent was decanted and freshly replenished three times a day. The single crystals of LIFM-114-S containing different organic solvents were obtained and applied for single crystal X-ray diffraction. Transformation of LIFM-114 into LIFM-114-T (T = 40, 60, 80, 100 oC, respectively). The pristine LIFM-114 was heated to different temperature and kept for 15 minutes. The resulted single crystals are mounted on the single crystal diffractometer and tested for structures of LIFM-114-T (T = 40, 60, 80 oC). For LIFM-114-100oC, the quality of the transformed single crystals is not good enough for data collection, and treated with PXRD Le Bail refinement. Transformation of LIFM-114 into LIFM-114-P (P = 8, 12, 16, 20 MPa, respectively). The pristine LIFM-114 powder sample was treated with different pressure using an isostatic pressure machine. The resulted samples were tested for PXRD Le Bail refinement. Transformation of LIFM-114 into LIFM-114-M (M means multiplexing pathways). Pathway I (P+T+P): The pristine LIFM-114 powder sample was treated with pressure 6 MPa, then heated to 60 oC, and then further treated with pressure 10 MPa. Pathway II (S+P+T+P): The pristine LIFM114 powder sample was immersed in Et2O for three days, then treated with pressure 6 MPa and heated to 60 oC, successively, and finally treated with pressure 20 MPa. Single Crystal X-Ray Crystallography. Single crystals of LIFM-114, LIFM-114-DCM, LIFM-114-EtOH, LIFM-114Et2O, LIFM-114-MeOH, LIFM-114-Toluene, LIFM-114-40oC, LIFM-114-60oC and LIFM-114-80oC were carefully picked and coated in paratone oil, attached to a glass silk which was inserted in a stainless steel stick, then quickly transferred to a Rigaku Oxford Gemini S Ultra CCD Diffractometer with the Enhance X-ray Source of Cu radiation 6N = 1.54178 Å) using the W X scan technique. All of the structures were solved by direct methods and refined by full-matrix least squares against F2 using the SHELXL programs.33 Hydrogen atoms were placed in geometrically calculated positions and included in the refinement process using riding model with isotropic thermal parameters: Uiso(H) = 1.2 Ueq(-CH). All the electrons of disordered solvent molecules which cannot be determined, are removed by SQUEEZE routine of PLATON program.34 Crystal and refinement parameters are listed in Table S1. Powder X-Ray Diffraction (PXRD) Index. Le Bail refinements have been performed with Jana2006.35 The unit cell parameters have been obtained from the PXRD patterns of LIFM-114cp, LIFM-114-100oC, and LIFM-114-8MPa, LIFM114-12MPa, LIFM-114-16MPa, LIFM-114-20MPa at room temperature based on the single-crystal structure of LIFM-114 determined at 150 K.
Results and Discussion Crystal Structure and Porosity. Light green crystals of LIFM-114 ({[(Zr6O4)(OH)8(ETTC)2(H2O)4]·solvents}n) were obtained through solvothermal reaction of ZrOCl2·8H2O and H4ETTC in DMF with formic acid as modulator at 120 oC. LIFM-114 crystallizes in the orthorhombic space group Fmmm (Figure 1, Tables S1, S2), possessing a neutral coordination
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the reversibility of the sample, it is necessary to use outer stimuli to recover the original structure. For the solvated samples, the structure can be recovered by immersing in DMF solvent. And for the samples get heated or compressed, the structure can be restored to original state via immersing in heated DMF (10 hours with TFA, or 20 hours without TFA). The results hint that the structural change is not only induced by changes in weak interlinker supramolecular interactions, but additional structural distortions including ligand transformation and sub-net sliding will need additional input energies for both transition occurrence and recovery. PXRD, IR, TG-MS, color detection and PL spectra all prove the structural transition and recovery processes of LIFM-114 by different stimulation pathways (Figures S16-37). As seen from Figure S38 and Table S4, for the recovered samples of LIFM-114-20MPa and LIFM114-100oC by heating in DMF containing TFA, the N2 adsorption isotherms show a Brunauer-Emmett-Teller (BET) surface area of 961 and 959 m2 g-1, respectively, similar with that of LIFM-114. In addition, the total pore volumes of the recovered samples are almost the same as that of the parent MOF. This ascertains the retention of porosity after outer stimuli treatment and rules out the possibility of framework collapse. Table 1. Dependence of the emission wavelength with lattice volume and ETTC conformations of LIFM-114 samples treated with different stimulation pathways. Path Sample
Volume Intra-Distance Inter-Distance /Å3 18988a
LIFM-114
T
P
/Å
/nm
17.3
10.7
489
b
LIFM-cp
15557
LIFM-114-40oC
18164a
16.9
9.6
490
LIFM-114-60 C
16535
a
16.2
8.6
528
LIFM-114-80oC
16077a
16.1
7.4
538
LIFM-114-100oC
15557b
545
LIFM-114-8MPa
b
519
LIFM-114-12MPa 16084b
532
LIFM-114-16MPa 15981b
536
o
545
17090
b
LIFM-114-20MPa 15779
545
LIFM-114-Toluene 18557a
16.9
9.9
486
17696a
16.7
9.0
500
LIFM-114-MeOH
16620
a
16.2
8.6
505
LIFM-114-DCM
16265a
16.1
7.5
510
LIFM-114-Et2O
15710a
16.2
7.4
516
LIFM-114-EtOH S
Em
/Å
aDetermined by single crystal data; bDetermined by PXRD Le Bail refinement.
Along with the framework contraction of LIFM-114, the ETTC chromophore linkers also show steady deformations. As illustrated in Figure 2b and Table 1, after solvents uptaking or heating, the intra-distance of ETTC shows a decreasing tendency as obtained from single-crystal data analyses (from the original 17.3 Å in LIFM-114 to 16.9, 16.2, and 16.1 Å after heating at 40, 60, 80 oC, and 16.9-16.2 Å after uptaking different solvent from toluene to Et2O, respectively). Moreover, since LIFM-114 is 2-fold interpenetrated, the inter-distance between two ETTCs from adjacent catenated networks constitute another important parameter to indicate the packing states between ETTC chromophores. As listed in Table 1, after
heating, the inter-distances between ETTCs are decreased from the original 10.7 Å in LIFM-114, to 9.6, 8.6, and 7.4 Å after heating at 40, 60 and 80 oC, respectively. Also, after solvent uptaking, the inter-distances are decreased to 9.9-7.4 Å from toluene to Et2O, respectively. Basically, for samples treated with more volatile solvents and higher temperature, both the intra- and inter- distances will be decreased more (see Table 1 for details). Since ETTC is a typical AIE molecule, these two parameters reflect the changes in the conformation and packing states of the chromophores, and can be directly correlated with the PL switching properties of the overall framework. Although due to technique restriction, we did not get the single crystal data for LIFM-114 samples under pressure. PXRD Le Bail refinement gave lattice volume parameters, with the same contraction tendency as temperature and solvent. By this, similar changes in the intra- and inter-distances of ETTC linkers might be proposed, and lead to corresponding PL color tuning. PL Tuning by Multiplexing Pathways. We then performed photophysical switching exploration of LIFM-114 along with the above structural transformation. Solid-state diffuse B %! % (Figure S39) manifests a narrower absorption band from 290 to 450 nm for LIFM-114, accounting for its bleached color compared with H4ETTC and LIFM-114cp. For clear comparison, LIFM-114 emits highly efficient blue PL maximized at 489 nm, with an absolute quantum yield ( ) of 61.3 % (Table S5), while LIFM-114cp emits yellow PL with peak maximum at 545 nm (near the PL position of H4ETTC ligand), which is almost 60 nm red-shifted and displays an increased quantum yield of 77.1 %. This shows an aggregation induced emission (AIE) effect, which is typical of the ETTC ligand containing TPE backbone. And the PL shift range we obtained in LIFM-114 of 56 nm (489-545 nm) is comparable with other AIE molecule based MOFs having sensing properties.14, 17, 36-39 More importantly, for LIFM-114, heating, pressing, or uptaking of volatile solvents all lead to the similar PL switching tendency (Figure 3 & Table 1), which prompts us to find whether a uniform guideline can be established among the different tuning pathways. First, we treated LIFM-114 with various solvents to get a series of LIFM-114-S samples. As we get from the above crystal structure analyses, the lattice volume gradually shrinks from LIFM-114-Toluene to LIFM-114-Et2O, and the inter- and intra- distances are also gradually decreased. This results in gradually intensified AIE effect, and red-shift of the emission peaks is observed. Comparative results show that the more volatile of solvents, the more red-shifted PL will be got for the obtained samples (Figure 3a). For instance, the emission maximum shifts to 486 nm after uptaking toluene, to 500 and 505 nm after uptaking EtOH and MeOH, while further shifts to 510 and 516 nm after treatment of DCM and Et2O, resulting in a steady change of PL color in the CIE coordinates. By this means, we actually get a series of intermediate PL states by treating LIFM-114 with different solvents, as plotted on the Saxis of Scheme 1. Similar PL tuning strategy for LIFM-114 can be implemented more efficiently and prominently by heating or pressing methods. For LIFM-114-T samples obtained at different temperature from 25 to 100 oC, the emission maxima are continuously red-shifted from 489 to 545 nm, with the PL color changes from blue to yellow (Figure 3b). The mechanism is similar to that for the solvent-uptaking samples. The temperature increase will cause shrinkage in the framework,
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535 nm successively, and ultimately, treated at 20 MPa (P) to result in an ultimate PL state with maximum at 540 nm. As additional multiplexing routes, we also conducted experiments for LIFM-114-Toluene with respect to successive pressure (S+P+P…), and LIFM-114-Et2O with respect to successive temperature (S+T+T…). The results are shown in Figures S40 & 41. It can be further concluded that, the various stages of PL states we accomplish through the present multiplexing approach bear the capability of memorization and accumulation simultaneously, and provide wonderful prototypes to be applied as composite nonvolatile data storage and so on.
Conclusions In summary, we have constructed a breathing catenated ZrMOF from TPE-based linker with structural deformation and AIE attributes. The MOF manifests unprecedentedly successive solvo/thermo/piezo-fluorochromism, which can be directly correlated with the structural deformation parameters. This allows for the access of an infinite number of PL states to rest on the S-, T- and P-axes of a 3D photoluminescence color tuning (PLCT) coordinate system, to achieve PL-tuning in a predictable and controllable manner by different routes. More importantly, via multiplexing approach to perform programmable relay operations among the PL states on S-, Tand P-axes, innumerous pathways can be established to reach various PL stages based on the nonvolatile memory nature of the intermediate states. This study gives a brand new concept on the PL tuning mechanisms and implementing paths for MOFs, and paves the way for further design and application of multi-stimuli responsive materials in advanced photoelectronic signal processing and so on.
ASSOCIATED CONTENT The Supporting Information is available free of charge on the ACS Publications website at DOI: XXXX. Methods and additional data (PDF) Crystallographic data in CIF format (ZIP)
AUTHOR INFORMATION Corresponding Author *
[email protected] Author Contributions ‡C.-X.C.
and Z.-W.W. contributed equally.
Funding Sources Any funds used to support the research of the manuscript should be placed here (per journal style).
Notes The authors declare no competing financial interest.
ACKNOWLEDGMENT This work was supported by NSFC (21720102007, 21771197, 21821003, 21603278), Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program (2017BT01C161), Chinese Postdoctoral Science Found (2017M622866), the International Postdoctoral Exchange Fellowship Program (20180055), and FRF for the Central Universities.
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Programmable PL-tuning by multiplexing S-T-P approaches for a breathing Zr-MOF with 2-fold catenation.
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