Novel CO2 Fluorescence Turn-On Quantification Based on a Dynamic

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Novel CO Fluorescence Turn-On Quantification Based on a Dynamic AIE-active Metal-Organic Framework Ming-Hua Xie, Wei Cai, Xiahui Chen, Rong-Feng Guan, Lu-Ming Wang, Gui-Hua Hou, Xin-Guo Xi, Qin-Fang Zhang, Xiu-Li Yang, and Rong Shao ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.7b17793 • Publication Date (Web): 22 Dec 2017 Downloaded from http://pubs.acs.org on December 24, 2017

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ACS Applied Materials & Interfaces

Novel CO2 Fluorescence Turn-On Quantification Based on a Dynamic AIE-active Metal-Organic Framework Ming-Hua Xie1, 2*, Wei Cai1, Xiahui Chen3, Rong-Feng Guan1, Lu-Ming Wang2, Gui-Hua Hou1, Xin-Guo Xi4, Qin-Fang Zhang1, Xiu-Li Yang 2*, Rong Shao 2* 1

Dr. M.-H. Xie, Mr. W. C., Dr. R.-F. Guan, Dr. G.-H. Hou, Dr. Q.-F. Zhang

Key Laboratory for Advanced Technology in Environmental Protection of Jiangsu Province, Yancheng Institute of Technology Yancheng, 224051 (P. R. China) E-mail: [email protected] 2

Dr. M.-H. Xie, Dr. L.-M. Wang, Dr. X.-L. Yang

Jiangsu Collaborative Innovation Center for Ecological Building Materials and Environmental Protection Equipments, Yancheng Institute of Technology, Yancheng, P. R. China 3

Dr. X. Chen

School of Electrical, Computer and Energy Engineering, Arizona State University, Tempe, USA Dr. X.-G. Xi School of Chemistry & Chemical Engineering, Yancheng Institute of Technology, Yancheng, P. R. China

ACS Paragon Plus Environment

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KEYWORDS CO2 fluorescence quantification, metal-organic frameworks, aggregation-induced emission, aggregation caused quenching, visible turn-on sensor, J aggregates

ABSTRACT

Traditional CO2 sensing technologies suffer from the disadvantages of being bulky, cross sensitive to interference such as CO and H2O, these issues could be properly tackled by innovating novel fluorescence-based sensing technology. Metal-organic frameworks (MOFs), which have been wildly explored as versatile fluorescence sensors, are still at a standstill for aggregation-induced emission (AIE) and no example of MOFs showing dynamic AIE activity has been reported yet. Herein, we report a novel MOF, which successfully converts the aggregation-caused quenching (ACQ) of the autologous ligand molecule to be AIE-active upon framework construction and exhibits bright fluorescence in highly viscous environment, resulting the first example of MOFs exhibiting real dynamic AIE activity. Furthermore, linear CO2 fluorescence quantification for mixed gas in the concentration range of 2.5-100% was thus well established. These results herald the understanding and advent of new generation in all solid-state fluorescence fields.

Introduction: Innovation in novel strategy for CO2 quantification is of great importance to environmental protection, occupational hygiene and early prediction of situations. For example, monitoring the CO2 fraction of mixed gas released by volcanos and hot springs may help to monitor the diastrophism and predict possible earthquakes. Quantification of CO2 concentrations of anthropogenic gases produced by industrial factories may help to maintain the proper functions of equipment and fight against the global warming effect caused by excess emissions of CO2


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gas.1 The currently adopted strategies of CO2 sensing are mainly based on electrochemistry (EC) or IR, and they are suffering from the intrinsic deficiencies including being bulky, power consuming, susceptible to the interference of CO and cross-sensitive to H2O.2,3 Establishing new CO2 sensing technology beyond EC or IR is urgently needed.

Figure 1. Structural illustration of ADA-Mn. a) Twisted L, the pale blue and brown squares represent the two planes created by two 6-member rings on the opposite side of the anthracence rings, and the dihedral angel of the two plane is about 3o. b) Twisted J aggregates in ADA-Mn, formed by the neighboring L. c) Top view of the 3D frameworks of ADA-Mn down the c axis. d) Representation view of the topological structures of ADA-Mn. Fluorescence sensing has been emerging as a reliable, fast and accurate sensing technology in many fields, with the advantage of being visible to the naked eyes which is superior to other sensing technologies.4-6 However, the development of fluorescence based CO2 sensor has been hindered due to the nonluminescence nature of CO2 as well as its chemical inertness, only very few substances, such as H2O, basic compounds, amines and primary alcohols could offer


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potential qualified reactions with CO2 for the purpose of establishing fast and selective sensing application under mild conditions. Among them, the reaction of CO2 with some amines may immediately yield highly viscous carbamate ionic liquid (CIL) quantitatively, offering us a potential platform of exploring novel CO2 sensors.7 Recently, reported by Tang and extensively studied world widely, a fascinating fluorescent phenomenon termed as aggregation-induced emission (AIE) is found operative in a special class of luminophoric molecules that exhibit strongly enhanced emission in the aggregated states.8,9 Viscosity has been accepted as one of the main factors for achieving AIE, thus the merger of AIE with CO2 fluorescence sensing could be accomplished. To successfully establish an AIE-based CO2 sensor, a proper AIE-active platform must be employed. Metal-organic frameworks (MOFs) have been regarded as promising fluorescence platforms for a variety of sensors in many fields.10-13 MOFs possess many advantages such as tailorable functions and architectures, high surface areas and precisely determined structures for in-depth mechanistic studies, the merger of MOFs and AIE could pioneer the researches of fluorescent materials and achieve hitherto impossible sensing applications. To this end, several AIEgens have been incorporated to build MOFs with AIE activities.14-22 However, those MOFs could only exhibit enhanced static fluorescence, as those potential AIE-active molecules have been fixed in frameworks with inhibited molecular motions, and to the best of our knowledge no MOF exhibiting real dynamic AIE activity has been reported so far. It is worth noting that the boundary between a polymer and an individual molecule is flexible, and the concept of molecule in MOFs should range from an individual ligand molecule to the whole unity. With this regard, we report a novel working principle of AIE, deriving the first example of real dynamic AIEactive MOF (ADA-Mn) with linear CO2 fluorescence quantification capability.


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Results and discussion: Orange needlelike crystal of ADA-Mn was synthesized by self-assembly of anthracence 9,10diacrylate acid (H2L, ADA) with Mn(II) under solvothermal conditions. H2L inherit the aggregation caused quenching (ACQ) effect of anthracene, and moderate green fluorescence could be observed when dissolved in common organic solvents in dilute concentration (Figure S7). However, differ from that of ADA-Cd, ADA-Mn showed barely no fluorescence either in the solid or the dispersed states (Figure S9).23 Single crystal analysis suggests that affected by the rotation of L bridged neighboring Mn3O subunits (about 17o), the expected planar acene rings of L are twisted with a dihedral angel of about 3o, and the neighboring L ligands are thus only approximately parallel to each other (Figure 1a). Each two neighboring L ligands form a twisted J aggregates (Figure 1b), and further propagate into a condensed 3D framework (Figure 1c, d). The nonplanar anthracene rings and twisted J aggregates impede the communications between the neighboring L ligands, resulting the observed nonfluorescence. Density Functional Theory (DFT) calculations of an ideal [(Mn3O)2L6] cluster at the B3LYP 6-31G level were carried out to gain insights into the non-emissive behavior. Calculations reveal that the ground highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) are mainly localized on the central Mn3O subunits, and time dependent DFT calculations indicate electron transitions from the peripheral π system to the central 3d5 Mn(II) at the excited state (ligand to metal charge transfer, LMCT, Figure 2). The open shell configuration of the Mn3O subunit may consume energy in a non-radiative way, and the calculated value of the oscillator strength is zero, in accordance with the actual fluorescence performance.


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Figure 2. Calculated electron cloud distribution of the frontier molecular orbitals of [(Mn3O)2L6] cluster. a) HOMO, ground state. b) LUMO, ground state. c) HOMO, first singlet excited state. d) LUMO, first singlet excited state. During the fluorescence research we noticed that there was a subtle distinction in the fluorescence intensity of different batches of samples with different particle size distributions. Further studies indicated that the smaller in particle size, the stronger in fluorescence, and particle size smaller than 0.8 µm offered similar fluorescence enhancement (Figures S10-19). Smaller particles may provide more possibilities of mutual collision. The very unusual behavior of ADA-Mn implies coherent connection between the particle collision and fluorescence intensity, which shares much in sprit with AIE. To verify ADA-Mn is AIE active, classic solvent systems (DMF/H2O, DMSO/H2O, THF/H2O and acetone/H2O) were selected to study the corresponding fluorescence (Figures S20-23). The unusual fluorescence behavior of ascending prior to descending with the growth of water fraction (fw) caused by the over introduction of


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water could only gave ambiguous results. Fluorescence spectra under different viscosity conditions, which could be conducted in the absence of H2O, were recorded in DMF/glycerol. The fluorescence was monotonously intensified with the growth of glycerol fraction (fg) (Figure 3a). Interestingly, a linear relationship between the fluorescence intensity and viscosity in the low viscous region was found (Figure 3b and Table S3, the viscosities varied from 1 to 52 mPa.s, corresponding to fg =5-55%). The fluorescence spectra at fg=55% were further recorded at different temperatures to confirm the correlation between viscosity and fluorescence. The fluorescence at -20 oC was intensified more than 10 times compared to that at 80 oC (Figure 3c). Again, the viscosity of the system in the range of 20-80 oC, which falls into the above mentioned linear region, shows exactly the same linear correlation with the fluorescence intensity (Figure 3d, Table S4). The viscosity-related tests unambitiously confirm the dynamic AIE activity of ADA-Mn, and the fluorescence works as a linear function of viscosity in the low viscous region. The fluorescence exhibited in high viscosity system is much like that of ADA-Cd, the fluorescence of which originates from the J aggregates.23 This very rare AIE type fluorescence turn-on suggests the existence of potential connections between particle size, viscosity and the J aggregates. UV-Vis spectra were recorded to monitor the formation of molecular aggregates under different viscosity conditions. It is clearly showed that when dispersed in low viscous solvent, only absorption ascribed to the ethylenic band was observed, no obvious absorption could be detected in the range of 400-500 nm (benzoic band), implying the existence of LMCT. When increased the system viscosity, the benzoic absorption centered at 407 nm appeared, with a new absorption peak centered at 492 nm emerged, clearly confirms the formation of molecular aggregates (Figure 4a).24-26 We speculate that by decreasing the particle size, the resulted MOF fragments may provide abundant surface exposed ligands, which could contact with the exposed


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ligands located on the surface of other fragments, and the collision between these ligands could form J aggregates beneficial to fluorescence. As illustrated in Figure 4b and 4c, overlapping of frontier orbitals resulted by proper molecular aggregation may establish more effective pathway for energy transfer, and bright fluorescence thus could be triggered (Figure S24). Considering necessary energy consumption in realistic environment, the tested fluorescence emission peaked at 525 nm is much close to that of the calculated results (503 nm, Table S2 and Figure S27). Decreasing particle size will increase the probabilities of forming good and bad aggregates simultaneously, higher viscosity could stabilize the formed J aggregates by hampering the molecular motions, and a balance may be approaching for particles smaller than 0.8 µm.

Figure 3. Viscosity related AIE activity studies of ADA-Mn in a mixed solvent of DMF/glycerol under different conditions. a) Fluorescence change of ADA-Mn in DMF/glycerol with growing fg


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value. b) Linear correlation between the fluorescence intensity and viscosity in the region of fg=5-55%. c) Fluorescence change of ADA-Mn in DMF/glycerol (fg=55%) at different temperatures. d) Linear correlation between the fluorescence intensity and viscosity in the range of 20-80 oC. The unprecedented successful transformation from ACQ to AIE as well as the excellent linear intensity-viscosity function offer us the opportunity of exploring the potential application in CO2 fluorescence quantification, by virtue of the viscous CIL yielded by reacting CO2 with amines. A series of amines were screened, and dipropylamine (DPA) was selected to carry out further studies (Figure S34). CO2 gas was bubbled into DPA dispersion of ADA-Mn to study the CO2 sensing ability, and a linear line for the plot of fluorescence intensity (lg10I) vs. the volume of CO2 was obtained (Figure 5a, b). Time dependent fluorescence spectrum gives consistent linear dynamic sensing results (Figure 5c, d). CIL was also directly added to the DAP dispersion of ADA-Mn to examine the effect of CO2 bubbling, and the resulted linear line is in accordance with that of CO2 gas bubbling (Table S5, Figures S35 and 36).


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Figure 4. Mechanistic studies for the observed AIE activity of ADA-Mn. a) UV-Vis spectra of ADA-Mn recorded at different viscosity, showing the formation of molecular aggregations. b) Illustration of the collision dictated J aggregates formation. c) Calculated electron cloud distribution of the frontier molecular orbitals of J aggregated H2L molecules at the first singlet excited state, molecular communication by orbital overlapping is clearly shown.


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Figure 5. Linear fluorescence sensing of CO2 under different conditions. a) Fluorescence spectra of ADA-Mn dispersed in DPA upon bubbling different amount of pure CO2 gas. b) Linear line for log10I - CO2 volume. c) Time dependent fluorescence spectrum of ADA-Mn dispersed in DPA upon continuously bubbling 10 mL of pure CO2 gas over 2 minutes. d) Linear line for log10I - Time. e) Fluorescence spectra of ADA-Mn dispersed in DPA upon bubbling N2/CO2 with growing fCO2. f) Linear line for log10I vs. fCO2.


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Mixed gas of CO2/N2 with different fraction of CO2 (fCO2) was selected as a model system to further check the quantitative sensing capability of ADA-Mn. The fluorescence intensity shows a monotonous increase with the growth of fCO2, and linear correlation for almost full concentration range (2.5-100%) is established, suggesting the capability of quantifying accurate CO2 concentration in practical applications (Figure 5e, f). The interference of H2O was also evaluated, and nearly identical data could be acquired when 1-10 µL of H2O was added prior to test (Figure S37).The whole sensing process is heterogeneous in nature, PXRD analysis of the recovered samples indicates the structural robustness, and no obvious loss in activity was observed after storage of samples in DMF/glycerol for 3 days (Figures S6, S38 and S39), suggesting the advantage of reusability and sustainability as potential CO2 fluorescence sensor. Conclusion: In summary, we describe here a novel working principle for the transformation of the very same molecule from ACQ to AIE by virtue of the subtle molecular manipulation in MOFs, and linear CO2 fluorescence quantification for mixed gas was also established. This work ushers in a frontier for the understanding in solid-state fluorescence, and could be generally applicable to many other solid fluorescence device fabrications. ASSOCIATED CONTENT Supporting Information. Figures S1-S39 and Tables S1-S5 give detailed information for the synthesis of ADA-Mn, AIE test experiment and DFT calculations.

CCDC 1517300

contains the supplementary

crystallographic data for this paper.


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AUTHOR INFORMATION Corresponding Author Email: [email protected] ORCID Ming-Hua Xie: 0000-0002-7959-6163 Notes The authors declare no competing financial interest. ACKNOWLEDGMENT This work was supported by the National Natural Science Foundation of China (Grant Nos. 21401160, 21775136, 21771158, 21301149 and 21276220), the Natural Science Foundation of the Higher Education Institutions of Jiangsu Province (Grant No. 17KJB150039), the 863 program of China (2015AA021003), research fund of Jiangsu Collaborative Innovation Center for Ecological Building Materials and Environmental Protection Equipments

(Grant Nos.

GX2015104 and CP201502), Talent Project of Yancheng Institute of Technology (Grant Nos. KJC2013001 and KJC2014034), and Research Fund of Key Laboratory for Advanced Technology in Environmental Protection of Jiangsu Province (Grant Nos. AE201310 and AE201312). We thank National Supercomputing Center in Shenzhen for providing the computational resources and Gaussian 09 package (D.01) and Prof. Daqi Wang of Liaocheng University for single crystal analysis.


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Novel CO2 Fluorescence Turn-On Quantification Based on a Dynamic

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