Recoverable Mechanoresponsive Luminescent Molecular Sponge

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Recoverable Mechanoresponsive Luminescent Molecular Sponge Material: A Novel Aryl Gold(I) Isocyanide Compound Meng-Juan Wang, Zhao-Yang Wang, Peng Luo, Bo Li, Li-Ya Wang, and Shuang-Quan Zang Cryst. Growth Des., Just Accepted Manuscript • DOI: 10.1021/acs.cgd.8b01495 • Publication Date (Web): 08 Jan 2019 Downloaded from http://pubs.acs.org on January 10, 2019

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Crystal Growth & Design

Recoverable

Mechanoresponsive

Luminescent

Molecular Sponge Material: A Novel Aryl Gold(I) Isocyanide Compound Meng-Juan Wang,a Zhao-Yang Wang,a Peng Luo,a Bo Li,*,b Li-Ya Wang,*,b and Shuang-Quan Zang*,a aCollege

of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001,

China. bCollege

of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang

473061, China.

ABSTRACT: A novel aryl gold(I) isocyanide complex with reversible sponge mechanoresponsive luminescent (MRL) property is reported. Upon grinding, the green-emitting crystals (1g) converted to a yellow-emitting amorphous state (1y). There are two ways to achieve the reversible process: after placing 1y for 10 hours at room temperature, an intermediate state generated and then adding DCM; 1g can be directly obtained by recrystallizing in DCM. The recovery is triggered by the weak halogen bonding and π∙∙∙π stacking interactions.

In recent decades, mechanoresponsive luminescent (MRL) materials have received a large amount of attention arising from their intrinsic nature, daedal structures and characterization, as well as

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their potential applications.1-5 Broadly, changes in crystal structure resulting from external mechanical stimulation lead to luminescence changes.6-11 For the aryl gold(I) isocyanide compounds that exhibit MRL properties, the luminescence changes mainly refer to changes of halogen bond interactions and π∙∙∙π interactions in the crystal structure.12-15 Upon mechanical stimulation, a single-crystal-to-single-crystal phase transition accompanied by red-shifted or blueshifted photoluminescence with incorporated weak or strong C-H∙∙∙π interactions was reported by Ito.16 The same author also utilized chiral steric hindrance paired with aurophilic interactions to cause a chiral-crystal-to-achiral-crystal phase transition, which accompanied a change of emission properties.17 Recently, Ito associated π∙∙∙π and C-H∙∙∙π interactions with aurophilic interactions to uncover a 9-anthryl gold(I) isocyanide complex that shows a spectral shift in emission from the visible to the IR region upon grinding.18 By some means, changes in the weak intermolecular interactions in the crystal-to-crystal phase transitions have an interesting influence on the change in luminescence.19-24 Halogen bond (XB) is primarily electrostatic in nature and is close to being a linear and noncovalent interaction.25-27 Y-X∙∙∙D can be used to described the XB. Among them, an electron poor region (a halogen atom, X) works as XB donor, and an electron donor (such as N, O, S, or halogen atoms) D works as XB acceptor.28-36 The application of the XB interactions to the aryl gold(I) isocyanide crystal structure has not been reported. We proposed that introduced moderatestrength halogen bonds would force the phase-transited crystal back to its initial crystal alignment upon grinding. Thus, we could establish a reversible sponge mechano-responsive luminescent mechanism via the moderate XB interaction. In this work, we synthesized a novel aryl gold(I) isocyanide compound 1 (Figure 1a). Recrystallization of compound 1 from dichloromethane (DCM) and methanol afforded green-


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emitting crystal 1g. Upon grinding, the green-emitting, colourless, needle-shaped crystalline compound 1g converted to a yellow-emitting amorphous state 1y. After placing the ground powder 1y at room temperature for 10 hours, it was surprising to find that the emission of the yellow emitting powder 1y had returned to green, which was almost consistent with the emission of 1g. Importantly, complex 1g could be wholely recovered by recrystallization of 1y in DCM. This result might be promisingly applied to memory materials. Reports of recoverable molecular sponge materials with mechano-responsive luminescent properties are rare.37 We conducted NMR measurements (Figure S1) and elemental analysis to test the purity of compound 1. Thermal gravimetric analysis (TGA) was performed to test the stability of complex 1g and amorphous state 1y (Figure S2). The bonds and functional groups contained in complex 1g were characterized though Raman spectroscopy (Figure S3). The phase purity of compound 1g was proven by powder X-ray diffraction (PXRD) patterns, which are consistent with simulated patterns based on single-crystal X-ray diffraction data (Figure S4).38 Afterwards, PXRD were employed to track the phase change and recovery caused by a mechanical trigger. At the same time, the variation in the emitted light was recorded by solid-state photoexcitation and emission spectroscopy. Raman spectra of 1g were obtained using a 633 nm laser as the excitation source at room temperature (Figure S3). To make proper peak assignments of the Raman spectroscopic data, Origin 8.6 software was used to process the data. There is activity in the CN stretching modes. Presumably, the fundamental vibration at 2203 cm-1 is the symmetric CN stretch.39-41 The strong band at 1571 cm-1 is recognized as a characteristic C-H vibration peak. The bands at 1168 cm-1 are associated with C-H inplane bending vibrations.42 The bands at approximately 1070 cm-1 are


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associated with C-C benzene ring stretching.43 However, in our study, the Au∙∙∙Au characteristic peaks were not observed in the nonresonant Raman spectra. Crystal structure analysis shows that 1g crystallized in the triclinic space group P-1. The linear molecules of 1g are head-to-tail bridged in the lattice through the N∙∙∙I halogen bonds with the bond distance of 3.110 Å, which is less than the sum of the Van der Waals radii of N and I (3.53 Å). Such one-dimensional chains are parallel arranged and further linked together by means of π∙∙∙π interactions of the benzene rings from adjacent chains with a distance between centroids of approximately 3.917 Å (Figures 1b, 1c). Each molecule adopts a nearly planar conformation with a 2.94º dihedral angle of the two phenyl rings. The shortest distance (3.781 Å) between the adjacent gold atoms indicates the absence of aurophilic interactions,44-47 and this result is consistent with our Raman spectra.

Figure 1. (a) Chemical structure of compound 1. (b) Packing diagram of 1g in the crystal structure viewed along the b axis. (c) Single crystal structure of 1g shown by a ball-and-stick


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representation with halogen bond and π∙∙∙π stacking interactions among the molecules. For clarity, only four molecules were taken out.

Figure 2. (a) Excitation (dash line) and emission spectra (solid line) for the unground (1g) and ground (1y) sample. (b) Emission spectral changes of 1y at room temperature over 10 h (λex = 386 nm). (c) Powder X-ray diffraction (PXRD) patterns of 1g (solid black line), 1y stored at room temperature for 0 h (solid red line) and 1y stored at -10 °C for 10 h (solid blue line). (d) PXRD of 1g (solid black line), 1y stored at room temperature for 0 h (solid red line), 5 h (solid blue line), 10 h (solid magenta line) and 1y recrystallized in DCM (solid green line). Complex 1g shows a noticeable change in luminescent colour from green to yellow under 365 nm UV irradiation after being rubbed vigorously in a mortar. The luminosity of 1y appears to be reduced relative to 1g (Figure 2a). PXRD analyses reveal that the transformation from 1g to 1y


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is a crystalline to amorphous transformation process (Figure 2c). We placed 1y at room temperature and -10 °C for 10 h, respectively. Placing 1y at room temperature for 10 h, we could detect the slow shift of its emission peak through its emission spectrum (Figure 2b). The powder 1y placed at room temperature for 10 h or recrystallized in DCM was returned to 1g (Figure 2d), while the powder 1y placed at -10 °C did not show any change after 10 h (Figure 2c). After the transition from crystalline phase 1g to amorphous phase 1y, which is a metastable state relative to 1g, the crystalline structure of 1y can recover to 1g across a low energy barrier at room temperature. The recovery process is blocked at low temperatures. This phenomenon of selfrecovery at room temperature without the use of additional energy has rarely been reported. To determine the origin of optical transformation, we simulated density functional theory (DFT) to study the optical absorption of 1g (Figure S5). Initially, we measured the optical properties of 1g and 1y. Crystal 1g in DCM solution had a main peak at 273 nm (HOMO → LUMO) assigned to ligand-to-ligand charge transfer (LLCT)48,49 (Figure S6). Before grinding, complex 1g showed significant green emission with a main peak at 500 nm and a shoulder peak at 530 nm. The absolute emission quantum yield (Φf) of 1g was 3.3%. The emissive lifetime of 1g on 500 nm and 530 nm were 0.43 ms and 0.53 ms, respectively (Figure S7 and Table S1). After strong grinding of 1g, the ground powder 1y induced a substantial emission colour change to yellow. The powder 1y presented a pronounced emission peak at 568 nm and a less pronounced shoulder at 496 nm, which overall showed a redshift compared to 1g emission peaks at 500 nm and 530 nm (Figure 2a). The optimal excitation wavelength of 1g is 363 nm, while the best excitation wavelength for 1y is 386 nm, which is red shifted by 23 nm from the optimum excitation wavelength of 1g. This difference indicates that 1y is more easily excited than 1g. The


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absolute emission quantum yield of 1y was 2.1%. The emissive lifetime of 1y at 496 nm and 568 nm were 0.31 ms and 0.36 ms, respectively (Figure S7, Table S1).

Figure 3. Schematic representations of the corresponding molecular arrangements and the molecules show ordered arrangement in 1g nevertheless chaos arrangement in 1y; the structure in image (c) shows a mixture of 1g and 1y. We made a guess and expressed it with a molecular schematic. Complex 1g is a crystal phase having green luminescence, and 1y is amorphous having yellow luminescence, and its 1y portion is restored to 1g, so that the PXRD phase exhibits a crystal phase of 1g. However, because there is still 1y in between, its luminescence is between 1g and 1y (Figure 3). This phenomenon


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coincides with the fact that the relative position of the 1y spectrum restored to its initial state of 1g after being left at room temperature for 10 h, but the relative height of the peak is not precisely the same. It could be wholely recovered by recrystallization of 1y in DCM (Figure 4). The molecules writhed from a disorderly, close packing to a loose-ordered, lamellar packing. However, at temperatures of -10 °C or lower, the reverse process was prevented because the thermal motion of the molecules was acutely weakened.

Figure 4. (a) Emission spectral 1g, 1y, 1y stored at room temperature for 10 h, and 1y recrystallized in DCM are denoted by 1, 2, 3 and 4 respectively. (b) CIE chromaticity diagram 1g, 1y, 1y stored at room temperature for 10 h, and 1y recrystallized in DCM are denoted by 1, 2, 3 and 4 respectively. PXRD of 1y was almost the same as 1g, but their emission peaks did not completely coincide. In this class of materials, examples of ground crystals that return to their original state without the application of additional conditions are relatively rare. Previous reports have shown that to recover this kind of material to the pre-polished state, grinding with solvents or heating would generally be necessary.50-54 The reason why 1y could recover from the polished state to the unground state was because of the introduced halogen bonds. Through the weak intermolecular interaction of the


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halogen bonds and π∙∙∙π stacking interactions, the object 1y could be restored to the initial state 1g across a lower energy barrier at room temperature. However, the strong extrusion force of grinding may cause a small amount of halogen bonds to be destroyed. Thus, it can be shown that although the powder X-ray diffraction analyses of the sample placed at room temperature for 10 h after grinding was exactly the same as 1g, the emission peaks did not completely coincide. In summary, we have proposed and proved one an effective strategy for achieving recovery through weak intermolecular interaction forces. In our work a complex 1g that can be mechanically triggered from a crystalline phase to an amorphous phase with a change in luminescence. This complex could return to its original state without any additional conditions at room temperature. We speculate that the mechanically triggered complex 1y may be in a metastable state and can be restored to its initial pre-grinding state over a lower energy barrier at room temperature through the synergistic effect of halogen bonds and π∙∙∙π stacking interactions. Although in our work this recovery is not complete, we called it reversible. These unusual properties may make this type of aryl gold(I) isocyanide compounds promising candidates for luminescent materials and memory light-emitting devices. ASSOCIATED CONTENT Supporting Information. The Supporting Information is available free of charge on the ACS Publications website at DOI: Crystallographic data, General Methods and Materials, General experiment procedures, TGA, PXRD patterns, Raman spectra, DFT and TDDFT Calculations, Emission decay curves (PDF) Accession Codes


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CCDC 1860498 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. AUTHOR INFORMATION Corresponding Author E-mail: [email protected]. E-mail: [email protected]. E-mail: [email protected]. ORCID Shuangquan Zang: 0000-0002-6728-0559 Liya Wang: 0000-0001-9125-859X Bo Li: 0000-0003-3440-759X Author Contributions The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript. Notes The authors declare no competing financial interest. ACKNOWLEDGMENT This work was supported by the National Natural Science Foundation of China (No. 21671175, 21671174, 21371153), the Program for Science & Technology Innovation Talents in Universities of Henan Province (164100510005) and Zhengzhou University. REFERENCES


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For Table of Contents Use Only

Recoverable Mechano-responsive Luminescent Molecular Sponge Material: A Novel Aryl Gold(I) Isocyanide Compound Meng-Juan Wang,a Zhao-Yang Wang,a Peng Luo,a Bo Li,*,b Li-Ya Wang,*,b and Shuang-Quan Zang*,a

Recoverable mechano-responsive luminescent molecular sponge via halogen bond and π∙∙∙π stack interaction. Upon grinding, the green-emitting crystals (1g) converted to a yellow-emitting amorphous state (1y). There are two ways to achieve the reversible process: after placing 1y for 10 hours at room temperature, an intermediate state generated and then adding DCM; 1g can be directly obtained by recrystallizing in DCM.


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Recoverable Mechanoresponsive Luminescent Molecular Sponge

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