Viedma Ripening of Chiral Coordination Polymers Based on Achiral

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Viedma Ripening of Chiral Coordination Polymers That Based on Achiral Molecules Shu-Ting Wu, Yu-Sheng Zhang, Bin Zhang, Xiao-Lin Hu, XiHe Huang, Chang-Cang Huang, and Nai-Feng Zhuang Cryst. Growth Des., Just Accepted Manuscript • DOI: 10.1021/acs.cgd.9b00235 • Publication Date (Web): 15 Apr 2019 Downloaded from http://pubs.acs.org on April 15, 2019

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Crystal Growth & Design

Figure 1 a) Schematic representation of the preparation for Cu-1 and Mn-2. b) The helical structures in space filling model of Cu-1 and Mn-2 in side view. Colour scheme: C, grey; O, red; N, blue; Cu/Mn, cyan. c) The connection fashion of the helixes in Cu-1 and Mn-2. The helixes were shown in space-filling model with diverse colours to distinguish with each other. The 4-4’-bipyridine ligands that connect the helix in Cu-1 were shown in ball and stick model. Hydrogen atom and solvent molecules were omitted for clarity. 149x134mm (300 x 300 DPI)

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Figure 2 a, b) The XRD patterns for Cu-1 (a) and Mn-2 (b) whose products were harvested under different preparation conditions. Legend scheme: “quick precipitation” means the preparation is performed in quick precipitation; “static” and “attrition” represent the preparation is performed in static or attrition state, respectively; “simulated” means the XRD pattern is the simulation of X-ray single crystal diffraction. c-e) The SEM images for Cu-1 that harvested in quick precipitation (c) or attrition preparation (d) and Mn-2 that prepared with attrition (e). f) The statistical distributions of particles sizes in c-e). 150x158mm (300 x 300 DPI)


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Figure 3 The CD spectra for Cu-1 (a) and Mn-2 (b) whose products were harvested under different preparation methods. Legend scheme is the same as Figure 2. 322x209mm (300 x 300 DPI)



Figure 4 a) Calibration curve of the CD peak intensity at 720 nm versus ee% for Cu-1. b) Attrition enhanced deracemization of Cu-1. Line is a guide to the eye. 493x189mm (300 x 300 DPI)


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Viedma Ripening of Chiral Coordination Polymers That Based on Achiral Molecules Shu-Ting Wu*,†,‡ Yu-Sheng Zhang,† Bin Zhang,† Xiao-Lin Hu,† Xi-He Huang,† Chang-Cang Huang,† and Nai-Feng Zhuang† †

Institute of Optical Crystalline Materials, College of Chemistry, Fuzhou University, Fuzhou, 350116, PR China. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, PR China. ‡

ABSTRACT: When the chiral coordination polymers were composed of achiral molecules, the deracemization of bulk product remains a great challenge if without any chiral induction. The Viedma ripening theory was adopted herein to help the achievement of mirror symmetry breaking for the bulk chirality of two chiral coordination polymers. The enantiomeric excess of the bulk chirality for the first compound is about 100%, which means absolute asymmetric synthesis. The deracemization degree of the bulk chirality for the second compound fluctuates occasionally. Further study has discussed the different deracemization degree of the bulk chirality for two compounds with the consideration of enantioselective incorporation in crystal cluster.

Introduction Chiral coordination polymers (CCPs) have attracted much attention due to their potential application in asymmetrical catalysis,1-8 chiral separation,9-12 second harmonic generation,13-15 ferroelectric property,16,17 etc. Generally, CCPs could be obtained by introducing certain chiral agents to play as components, counter ions, templates or structural directing agents.18-20 The limited species of commercial chiral agents and their high cost have hindered the development of CCPs. On the other hand, people have found that CCPs could also be prepared by adopting normal achiral starting materials, without any chiral agents (named aCCPs in the following discussion).21-35 This phenomenon is usually called “spontaneous resolution”. However, the products of those aCCPs were always racemic mixture (conglomerates) or racemic solid solution,36 which makes the study of application even difficult. To date, there are several attempts to study the mirror symmetry breaking (or chiral symmetry breaking in some references) of aCCPs, such as seeding,21 chemical manipulation,37 and physical field induction.38 However, seeding method requires homochiral crystal seeds and good chemical stability in the reaction. The requirement of chemical manipulation in the mirror symmetry breaking of aCCPs is often specific and strict. In our previous study, circular polarized light was adopted as chiral physical field to induce the enantioselective crystallization of aCCPs.38 However, the efficiency remains weak and the instrumental requirement is expensive. So it is urgent to find a simple and convenient method to modulate the asymmetric crystallization of aCCPs. Studies of the attrition assisted crystallization of NaClO3 crystals have shown promising application in the deracemization of chiral crystals.39 Beside NaClO3, people have succeeded in the deracemization of certain ionic crystals (NaBrO3,40 ethylenediammonium sulfate,41,42 etc) or molecular crystals (amino

acid derivatives,43-45 chiral sulfoxide,46 achiral aromatic compounds,47 drug molecules48-50 and coordination complex51) by adopting similar attrition method. Viedma ripening theory was then proposed to explain the attrition assisted deracemization, which includes four requirements as follows: i) racemization in solution, ii) Ostwald ripening, iii) enantioselective incorporation and iv) attrition.52 Considering the preparation of aCCPs adopts totally achiral compounds, which means the solution is possibly racemic, there is a chance for aCCPs to adopt Viedma ripening. Herein, two reported aCCPs were chosen as follows: Cu-1 represents the [P/M-Cu(succinate)(4-4’-bipyridine)]n·4nH2O compound,37 Mn-2 represents the [P/M-Mn(L1)(H2O)2]n compound (H2L1 = 5-(pyridine-3-yl)isophthalic acid).53 Both compounds crystallize in hexagonal crystal system. The space group for Cu-1 is P6122 (P6522). The space group for Mn-2 is P61 (P65). As shown in Figure 1, the crystal structure of both compounds features one-dimensional helix that interconnected with each other into three-dimensional network. Unexpectedly, although adopting similar attrition assisted preparation process, the two aCCPs exhibit different results in the deracemization degree.

Figure 1 a) Schematic representation of the preparation for Cu-1 and Mn-2. b) The helical structures in space filling model of Cu-1 and Mn-2 in side view. Colour scheme: C, grey; O, red; N, blue; Cu/Mn, cyan. c) The connection fashion of the helixes in Cu-1 and Mn-2. The helixes were shown in space-filling model with diverse colours to distinguish with each other. The 4-4’-bipyridine ligands



that connect the helix in Cu-1 were shown in ball and stick model. Hydrogen atom and solvent molecules were omitted for clarity. According to the previous study in the reference 37 and 53, the mirror symmetry breaking of Cu-1 could be achieved by chemical manipulation in a very slow crystallization (more than one month). The bulk product of rapid crystallization of Cu-1 was racemic mixture. For Mn-2, the bulk crystalline product was also racemic mixture. Repeated experiments for Cu-1 and Mn-2 were tried. For Cu-1, it was found that the target product could be obtained by quick precipitation in pH = 8.87. When adjust the pH to 9.74, either static crystallization (3-5 days) or attrition assisted crystallization (38 hours) could offer the target product. For Mn-2, the mixing procedure performed at 100 oC. No quick precipitation was formed. The target product would be obtained in either static crystallization (1-2 days) or attrition assisted crystallization at 100 oC (up to 30 hours). All the product purity was confirmed by X-ray powder diffraction (Figure 2a, b). The Rietveld refinement of XRD further confirmed the crystalline structure is identical to the reported one (Table S1-S2, Figure S1-S5). The attrition was executed by in situ magnetic stirring with some small glass beads.

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sizes range from 0.1 ~ 2 microns (Figure 2f). So it is significant that attrition greatly destroys crystals into smaller pieces, and consequently encourages the secondary nucleation to form crystal clusters. For Mn-2, after attrition, there are two kinds of particle shape. One is rod shape with hexagonal pyramid in the end, the others is tiny ball-like particles. The particles sizes are similar to that of Cu-1 (Figure 2e & f), which indicates the attrition effect in both case may be similar. The enantiomeric excess level of the target product in each run was tested by solid state circular dichroism (short for CD) spectrum. The spectral measurement and the preparation of the sample disks were executed in exactly the same procedure for the comparison of the CD intensity at characteristic absorbance band (experimental detail is in ESI).

Figure 3 The CD spectra for Cu-1 (a) and Mn-2 (b) whose products were harvested under different preparation methods. Legend scheme is the same as Figure 2.

Figure 2 a, b) The XRD patterns for Cu-1 (a) and Mn-2 (b) whose products were harvested under different preparation conditions. Legend scheme: “quick precipitation” means the preparation is performed in quick precipitation; “static” and “attrition” represent the preparation is performed in static or attrition state, respectively; “simulated” means the XRD pattern is the simulation of X-ray single crystal diffraction. c-e) The SEM images for Cu-1 that harvested in quick precipitation (c) or attrition preparation (d) and Mn-2 that prepared with attrition (e). f) The statistical distributions of particles sizes in c-e). SEM study reveals that the product of Cu-1 that harvested in quick precipitation adopts dispersed hexagonal dipyramids with particle size about 2 ~ 9 microns (Figure 2c). There are cross breakages on the surface of the dipyramids which should be attributed to dehydration in the high vacuum of SEM measurement. Actually, the cleavage plane for Cu-1 crystals is always the plane (0 0 1). As shown in Figure 2d, Cu-1 that prepared in attrition crystallization exhibits smaller irregular particles. The particles

As shown in Figure 3a, the CD spectra of Cu-1 that harvested under the three different preparation conditions show significant different optical activity in the absorbance band. Quick precipitation generates the product Cu-1 with almost CD silent (-5 ~ +1 mdeg at 720 nm) in 6 parallel experiments. Static crystallization generates either dispersed crystals or crystal clusters, showing weak CD intensity (+1 ~ +8 and -1 ~ -14 mdeg at 720 nm) in 15 parallel experiments. Attrition assisted crystallization generates powder product, whose CD intensity range from 52 to 61 mdeg and -50 to -60 mdeg at 720 nm in 20 parallel experiments. Consequently, the Cu-1 products that made in attrition crystallization show obvious and repeatable mirror symmetry breaking. For Mn-2, the CD spectra for the static cases all show weak intensity in the absorbance band (-5 ~ 0 mdeg at 245 nm) in 8 parallel experiments (Figure 3b). The CD spectra for the attrition cases show various intensities (+1 ~ +11 and -15 ~ -30 mdeg at 245 nm) in 14 parallel experiments. So, it seems that mirror symmetry breaking occasionally occurs in the attrition assisted preparation of Mn-2, the deracemization degree varies in multiple repeated runs. Consequently, the CD study for Cu-1 and Mn-2 reveals significant different effect when adopting the same attrition approach. Considering the four requirements of Viedma theory, the enantioselective incorporation of Cu-1 and Mn-2 was studied by analysing the crystals’ chirality in the crystal cluster. In the non-classical models of crystallization, it is postulated that crystals can grow due to the attachment of solid phase blocks rather than single atoms.54 Rapid development of material science such as nanomaterial and biomaterial have suggested that non-classical crystallization model also involve the common nucleation stage. The so-called oriented attachment in the non-classical crystallization models shows possibility of enantiomeric selective in the study of NaClO3 and NaBrO3 crystals,55 gypsum crystals,56


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guanidine carbonate crystals.57 Similarly, the study of Cu-1 in reference 37 also suggests the enantioselective incorporation within the crystal cluster. Based on the study of SEM (Figure 2d), attrition greatly encourages the secondary nucleation which leads to a large amount of crystal cluster. The enantioselective incorporation thus benefits the homochirality enlargement. For Mn-2, when we tested the crystal chirality in the crystal cluster, it is surprising that the enantioselective rule does not perform well. 26 single crystals that grown in five separated crystal clusters were tested by the X-ray single crystal diffraction (Table S4 in ESI). The absolute configuration was studied by the Flack parameter of anomalous scattering,58 showing that three crystal clusters are homochiral, two clusters are heterochiral. Consequently, the weak enantioselective incorporation of Mn-2 may be the reason for the stochastic fluctuating of the deracemization degree. Further study of Cu-1 involves the time dependent attrition effect. To quantitatively evaluate the CD intensity with the enantiomeric excess of Cu-1, the calibration curve of the CD peak intensity (720 nm) and the enantiomeric excess was established by adopting single crystals with known chirality for CD spectra (Figure 4a). By the help of calibration curve, it is found that the enantiomeric excess value of product increases by simply extending the attrition time. Further, the enantiomeric excess of target product is closed to 100% when attrition for 30 hours, which means the absolute asymmetric synthesis might be achieved for Cu-1 (experimental detail is in ESI).

AUTHOR INFORMATION Corresponding Author Shu-Ting Wu E-mail: [email protected] ORCID: 0000-0002-7026-7806

Author Contributions Shu-Ting designed the research; Yu-Sheng and Bin Zhang performed the research; Shu-Ting and Yu-Sheng analyzed data and wrote the paper; Shu-Ting, Xiao-Lin, Xi-He, Chang-Cang and NaiFeng discussed and made helpful advices. All authors have given approval to the final version of the manuscript.

Notes The authors declare no competing financial interest.

ACKNOWLEDGMENT We thank the financial support from the National Natural Science Foundation of China (21671041, 61875039), the Natural Science Foundation of Fujian Province (2016J01688), the State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, CAS (20160010); Fuzhou University Testing Fund of precious apparatus (2018T007); and the undergraduate innovation training program of Fuzhou University (201810386005).

REFERENCE (1)

Figure 4 a) Calibration curve of the CD peak intensity at 720 nm versus ee% for Cu-1. b) Attrition enhanced deracemization of Cu1. Line is a guide to the eye. Conclusion Two chiral coordination polymers that based on achiral molecules have been studied about their Viedma ripening behaviour. It is fascinating that both compounds exhibit the mirror symmetry breaking upon attrition crystallization. One of them even achieves the absolute asymmetric synthesis. By the help of Viedma theory, the diverse deracemization degrees that occurs in the two compounds was attribute to their different enantioselective incorporation characters in the crystal cluster. Further, study around the enantioselective incorporation in crystal cluster is undergoing. It is hopefully that the work herein would offer a simple but efficient method to study the mirror symmetry breaking or absolute asymmetric synthesis of chiral coordination polymers that based on achiral molecules.

ASSOCIATED CONTENT Supporting Information Electronic Supplementary Information (ESI) available: Experimental details including materials, characterization, synthesis, time dependent attrition effect experiment, X-ray powder diffraction data and Rietveld refinement, X-ray single crystal diffraction data, refinement parameters, and the absolute configuration of 26 single crystals for Mn-2. Accession codes. The complete crystal data could be obtained in CCDC 1885585-1885610 for Mn-2.

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Viedma ripening of chiral coordination polymers that based on achiral molecules Shu-Ting Wu*,†,‡ Yu-Sheng Zhang,† Bin Zhang,† Xiao-Lin Hu,† Xi-He Huang,† Chang-Cang Huang,† and Nai-Feng Zhuang†

The Viedma ripening of two chiral coordination polymers that based on achiral molecules were studied, showing the mirror symmetry breaking for both crystalline products during the attrition crystallization procedure.


Viedma Ripening of Chiral Coordination Polymers Based on Achiral

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