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Anion-induced differential assembly and structural transformation of supramolecular coordination cages
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Shao-Ping Zhenga, Yao-Wei Xua, Pei-Yang Sua, b, Chen-Hui Liua, Yin-Hui Huanga, Yu-Lin Lua, Zhang-Wen Weia, Zhiwei Jiaoa, Hai-Sen Xu*, a, Cheng-Yong Su*, a, c
Chinese Chemical Letters | 2024, 35(3) : 108477
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Chinese Chemical Letters | 2024, 35(3): 108477
• Communication •
Anion-induced differential assembly and structural transformation of supramolecular coordination cages
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Shao-Ping Zhenga, Yao-Wei Xua, Pei-Yang Sua, b, Chen-Hui Liua, Yin-Hui Huanga, Yu-Lin Lua, Zhang-Wen Weia, Zhiwei Jiaoa, Hai-Sen Xu*, a, Cheng-Yong Su*, a, c
Affiliations
  • a MOE Laboratory of Bioinorganic and Synthetic Chemistry, Lehn Institute of Functional Materials, School of Chemistry, Sun Yat-sen University, Guangzhou 510006, China
  • b Institute of Environmental Research at Greater Bay Area, Guangzhou University, Guangzhou 510006, China
  • c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Published: 2024-03-15 doi: 10.1016/j.cclet.2023.108477
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The intimate host-anion interactions will regulate thermodynamics and kinetics in the self-assembly of cationic cages mimicking biological counterparts. Herein, we report construction and transformation of three Pd(Ⅱ)-based metal-organic cages (MOCs) depending on different anions. Stoichiometric conversions of the lantern-shaped MOC-34 into either octahedral MOC-35 or tricapped trigonal prism MOC-36 are induced by BF4‒ or NO3‒, respectively. MOC-36 is kinetically favored and can undergo quantitative conversion to the thermodynamically preferred MOC-35 upon heating, accelerated by excess BF4‒ to motivate dissociative dynamics of Pd-vertices and lower activation barrier of cage transformation. The guest encapsulation behaviors of MOC-35 and MOC-36 have also been tested. These results manifest a significance of host-anion dynamics beyond complementary anion template, shedding light on the understanding of intricate anion recognition in nature.

Supramolecular coordination cage  /  Dynamic host-anion interactions  /  Structural transformation  /  Anion receptor  /  Guest inclusion
Shao-Ping Zheng, Yao-Wei Xu, Pei-Yang Su, Chen-Hui Liu, Yin-Hui Huang, Yu-Lin Lu, Zhang-Wen Wei, Zhiwei Jiao, Hai-Sen Xu, Cheng-Yong Su. Anion-induced differential assembly and structural transformation of supramolecular coordination cages[J]. Chinese Chemical Letters, 2024 , 35 (3) : 108477 - . DOI: 10.1016/j.cclet.2023.108477
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The generation of exquisite and complex architectures from relatively simple molecular precursors through noncovalent interaction is ubiquitous in nature [1]. Over the past decades, the self-assembly of metal-organic cages (MOCs) offers a controllable platform at the molecular level to mimic biological counterparts such as protein receptors and enzymes [2–4], in which the spatial arrangement and directionality of the components are well-defined owing to a thermodynamic control of the error correction of the reversible bonds [5,6]. However, different self-assembling progresses often equilibrate to present a distribution in delicate balance, which is tunable depending on external stimuli [7–9], e.g., guest [10,11], concentration [12,13], solvent [14–16], etc. Substantial effort has been devoted to illuminating the principles governing the self-assembly processes from the same building blocks [17–19] nevertheless, precise prediction in many cases still remains an elusive challenge [5,20,21].
Benefited from electrostatic and hydrogen-bonding interactions, anions have been widely employed in self-organization [22], recognition [23–25] and transformation [26,27]. For instance, anionic templates with shape complementarity and ideal packing coefficient were added to the system to drive the formation of inaccessible complicated supramolecular architectures [15,28]. In addition to the mutual matching host–guest complexation [29], dynamic associations of the counterions around a cationic host with large holes opening to the exterior are common phenomena in solution, but are neglected in most cases. Such anion binding may impose elaborate perturbation on the constitutional dynamic libraries (CDLs) [7,8] in solution, thus resulting in various thermodynamic and/or kinetic binding events to lead to structural regulation [30–32], reminiscent of the induced-fit mechanism observed in biological receptors [33]. Moreover, it is of interest to explore how the supramolecular isomerism in coordination self-assembly can be controlled by anions in different structural orders, considering that it has been extensively investigated in polymeric and cyclic systems [20,34–36], but less studied in cage system, compared other external stimuli such as guests, concentration, solvent, pH, and light [12,17,26,28,37–39].
Here, we report differential assembly and transformation of three MOCs, i.e., one Pd2L4 (MOC-34) cage and two (Pd3L4)2-3 supramolecular isomeric cages (MOC-35 and MOC-36), induced by BF4‒ or NO3‒ anions (Scheme 1). Based on the experiments and theoretical calculations, we find that the host-anion dynamic interactions play a significant role beyond anion template effect in the regulation of thermodynamics and kinetics in cage transformation. The anion-induced interconversion between the smaller Pd6L8 and larger Pd9L12 can tune the confined environment, thus generating distinct host–guest interactions for guest inclusion.
A tridentate torsional compound, tris(4-(pyridin-3-yl)phenyl) amine (L), was synthesized as the organic ligand. Owing to the C3-symmetric propeller shape and the free twist of NPy-sites, its assembly with the four-coordination Pd2+ is expected to form different cage structures with variable composition (Scheme 1 and Fig. 1). A lantern-shaped cage MOC-34 was obtained by mixing L and 0.5 equiv. Pd(NO3)2 or [Pd(CH3CN)4](BF4)2 in DMSO at room temperature for 2 h. 1H NMR spectrum presents proton signals corresponding to a Pd2L4 cage structure containing the degraded C2-symmetric ligand, which has been fully characterized by 13C, 1H-1H COSY, 1H-13C HSQC, 1H DOSY NMR and ESI-HR-MS (electrospray ionization−high-resolution mass) spectral measurements (Figs. S1–S7 in Supporting information). The single-crystal diffraction analysis (Fig. 1a and Table S1 in Supporting information) confirms that MOC-34 is composed of four bidentate ligands and two Pd2+ cations, in which only two NPy-sites of each ligand participate in coordination with the Pd-centers, leaving one pyridyl arm uncoordinated.
Since the tridentate ligands in MOC-34 show unsaturated coordination, we expect that even larger cage structures could be self-assembled by increasing the feeding ratio of metal/ligand (Pd/L > 1/2). Indeed, a clear solution was obtained by mixing L and 0.75 equiv. [Pd(CH3CN)4](BF4)2 (Pd/L = 3/4) in DMSO at 353 K for 4 h, and the 1H NMR spectrum displayed an uniformed proton signal pattern (Fig. S1) experiencing apparent downfield shift when compared with the free ligand, indicating that the three pyridyl arms are C3-symmetrically coordinated with Pd-centers to constitute a Pd6L8 type cage (MOC-35, Scheme 1 and Fig. 1b). The formation of Pd6L8 cage structure has been further confirmed by the detailed NMR and ESI-HR-MS spectral measurements (Figs. S8–S13 in Supporting information), in which the single diffusion band (logD = −10.1) in 1H DOSY spectrum suggests a dynamic radius of 13.8 Å for the cage (Fig. S12), and the neat series of successively charged [(Pd6L8)12++nBF4](12-n)+ species indicate the presence of the sole MOC-35 product in solution (Fig. S13). The single-crystal structure of MOC-35 (Fig. 1b and Tables S2 in Supporting information) unambiguously revealed an octahedral Pd6L8 cage consisted of eight ligands and six Pd2+ ions, where the square-planar coordination of Pd-center is accomplished by four Pd-N bonds. The triphenylamine skeleton in L maintains the torsional C3-symmetry, while pyridine moieties are twisted from planarity to wrap around the Pd-vertices (Fig. 1b). The distance along the diagonal of MOC-35 is measured to be 26 Å, in consistence with above DOSY estimation.
It is a surprise that with the same feeding ratio of Pd/L = 3/4 by using Pd(NO3)2 instead of [Pd(CH3CN)4](BF4)2, a new cage structure was assembled (MOC-36) under similar conditions (Scheme 1), which exhibits distinct and complicated NMR signal profiles as compared with MOC-34 and MOC-35 (Figs. S1 and S14–S16 in Supporting information). The careful analyses of the 1H-1H COSY and 1H-13C HSQC spectra suggest that the C3-symmetry of L ligands in this cage is seriously distorted, and three sets of proton signals are well resolved (Figs. S15 and S16), indicating a much lower symmetry of MOC-36 than the octahedral MOC-35. The 1H DOSY spectrum of MOC-36 (Fig. S17 in Supporting information) confirms that all proton signals have the same diffusion coefficient (logD = −10.17), giving a dynamic radius of the cage at approximate 16.1 Å, which means MOC-36 has a larger cage size than MOC-35 (32 vs. 26 Å). The ESI-HR-MS spectrum shows a series of sharp peaks (Fig. S18 in Supporting information), exactly corresponding to the charge states of a Pd9L12 type cage varying from +10 to +5, namely, [(Pd9L12)18+ + nNO3](18-n)+ species which show perfect matching of the experimental and simulated isotopic patterns.
Unfortunately, we failed to grow its single-crystals suitable for X-ray diffraction although many efforts have been devoted. Therefore, optimization of the cage structure based on energy minimization was carried out, yielding a best fit cage model of tricapped trigonal prismatic geometry (Fig. 1c and Fig. S19 in Supporting information). Six Pd-centers constitute the vertices of a trigonal prism, the rest three Pd-centers serve as the side capping vertices, and twelve tridentate ligands occupy the lateral triangular faces. From the top view, MOC-36 shows a general reuleaux triangle shape of C3-symmetry; therefore, the size of MOC-36 can be estimated as 32 × 23 Å when viewed along or perpendicular to the C3-axis (Fig. S19), in good agreement with the result calculated from the 1H DOSY spectrum.
To our knowledge, the unique cage geometry of MOC-36 has not been seen before in coordination cages. When compared with MOC-35, the two cage geometries are related (Fig. S20 in Supporting information). MOC-36 consists of three quadrangular pyramids formed by three rectangular sides of the trigonal prism with three capping vertices, which are connected to form the reuleaux triangle shape. Similarly, MOC-35 has two quadrangular pyramids glued together face-to-face. The dihedral angles between the pyramids are different in the two cages, with MOC-36 having a larger angle, leaving more space for anion interactions (Fig. S20). This geometric difference may be the reason for the anion-induced cage transformation (vide infra). The low symmetry of the trigonal prismatic MOC-36 makes the three pyridyl arms of each L ligand distinct, distinguishable from the positions to bind to different Pd-vertices (Fig. 1c). This explains why three sets of proton signals are observed in the NMR spectra of MOC-36 (Figs. S15 and S16).
The above experiments showed that the type of cage formed depends on the metal-ligand ratio, with Pd/L ratios of 1/2 and 3/4 leading to MOC-34 and MOC-35/36, respectively. To explore cage interconversions, Pd2+ salt, L ligand, and ethylenediamine (en) chelator were added to seize Pd2+ from the cage (Scheme 1 and Figs. S21–S35 in Supporting information). Adding Pd(CH3CN)4(BF4)2 to a solution of MOC-34-BF4 resulted in a single product transformation to MOC-35-BF4, while adding Pd(NO3)2 to a DMSO solution of MOC-34-NO3 led to quantitative conversion to MOC-36-NO3 (Figs. S21–S24). The reverse cage conversion from MOC-35 or MOC-36 to MOC-34 was also observed when L ligand or en was added (Figs. S25–S35 in Supporting information). In such reversible transformation processes, excess Pd2+ salt or L ligand had little influence on the directional cage conversions, but excess en chelator destroyed the cage to liberate free L ligand. These results suggest that the Pd-N coordination allows for dissociation and association of the L ligand, but the Pd-L exchange speed is slower than the NMR time scale.
Counter anions are crucial in regulating the assembly and transformation of cage structures to form supramolecular isomers MOC-35 or MOC-36. To study the impact of mixed BF4‒ and NO3‒ anions on the transformation process, Pd(NO3)2 or Pd(CH3CN)4(BF4)2 was added to the DMSO solution of MOC-34-BF4 or MOC-34-NO3, respectively. A dynamic mixture of MOC-35 and MOC-36 was observed using NMR analysis (Figs. S36 and S37 in Supporting information) [7,8]. In contrast, using only one type of anion leads to the formation of one product: BF4‒ leads to MOC-35 and NO3‒ leads to MOC-36. Both cages remain stable at room temperature for an extended period (Figs. S38 and S39 in Supporting information), but at elevated temperatures, MOC-36 transforms to MOC-35, and not the other way around. MOC-36 remains unchanged below 333 K but slowly transforms to MOC-35 above this temperature (Figs. S40–S48 in Supporting information). It takes 15 days for complete conversion to MOC-35-NO3 at 353 K (Fig. S44 in Supporting information). NMR analysis shows that the converted MOC-35-NO3 has a comparable cage size to the self-assembled MOC-35-BF4 (Fig. S49 in Supporting information), but a stronger host-NO3 interaction based on the remarkably downfield shifts of Hd in MOC-35 (Fig. S50 in Supporting information), indicating dynamic host-anion interactions underneath the Pd-vertices. Heating accelerates the cage transformation, with a rate constant of 5.02 × 10−10 mol L−1 s−1 at 353 K and an activation barrier of 123.9 kJ/mol. These experiments suggest that MOC-36 is kinetically favored, while MOC-35 is thermodynamically preferred.
The anion effect on the cage isomerization has been further studied by adding [(n-Bu)4N]BF4 to MOC-36 (Fig. S52 in Supporting information). Despite BF4‒ having weaker binding affinity than NO3‒, adding large excess of BF4‒ leads to competition with NO3‒ to dominate host-anion interactions, resulting in a significantly increased MOC-36-to-MOC-35 conversion rate (Figs. S52–S61 in Supporting information). Adding 180 equiv. BF4‒ leads to a complete MOC-36-to-MOC-35 conversion in 72 h at 353 K (Fig. 2a), over five times faster than the conversion without BF4‒ anions. At a higher temperature, the conversion is even more rapid, taking only 10 h at 373 K (Fig. 2b and Fig. S58 in Supporting information). The conversion rate at 353 K is calculated to be k = 2.87 × 10−9 mol L−1 s−1, over five times faster than the rate without BF4‒ anions. The conversion activation barrier for MOC-36 is significantly lower at 106.6 kJ/mol under 180 equiv. BF4‒ condition (Fig. S61 in Supporting information), indicating a significant role of host-anion dynamic interactions in altering the energy barrier for MOC-36-to-MOC-35 structural transformation with BF4‒ anions. However, a reversible MOC-35-to-MOC-36 cage conversion is difficult to achieve, no matter by heating (Fig. S39) or adding excess NO3‒ anions (Fig. S51).
More information about host-anion interactions was provided by the single-crystal structural analyses of MOC-35-NO3 and MOC-35-BF4 (Figs. 3a and b). Six anions are bound inside pockets underneath the Pd-vertices, forming C-H···O or C-H···F hydrogen bonds with the host through the pyridyl and phenyl rings. Density functional theory (DFT) calculations for fragmental NO3@[Pd(Py-Ph)4]2+ and BF4@[Pd(Py-Ph)4]2+ (Py = pyridyl, Ph= phenyl) were carried out based on the single-crystal structures of MOC-35-NO3 and MOC-35-BF4, respectively. The total binding energy per anion for MOC-35-NO3 is calculated to be −545.7 kJ/mol, while for MOC-35-BF4, it is −583.8 kJ/mol. In MOC-35, the tetrahedral BF4‒ shows better shape complementarity than the planar NO3‒, although the latter has stronger individual hydrogen bonding. We also calculate the total binding energies per anion for NO3@[Pd(Py-Ph)4]2+ or BF4@[Pd(Py-Ph)4]2+ units based on the simulated structure of MOC-36 (Figs. 3c and d), giving significantly different enthalpy values of −595.6 kJ/mol for MOC-36-NO3 and −551.2 kJ/mol for the postulated MOC-36-BF4. It is apparent that the NO3‒ binding is much more conducive to stabilize the Pd-vertices in MOC-36 than the BF4‒ binding, which adequately explains why the cage structure of MOC-36 is easily generated in the presence of NO3‒ anions.
The crystal structure analysis and theoretical calculations presented here support experimental observations of anion-induced cage self-assembly and transformation. The tetrahedral BF4‒ fit best in MOC-35's vertex pockets, while planar NO3‒ fit best in MOC-36's, forming strong host-anion interactions. This controls the stoichiometric cage transformation from MOC-34 to MOC-35 with BF4‒ and MOC-36 with NO3‒. The Pd-N coordination is intrinsically dynamic, allowing for cage isomerization from kinetically favored MOC-36 with tensive N-Pd-N dihedral angles to thermodynamically preferred MOC-35 with relatively relaxed N-Pd-N dihedral angles. While MOC-36 is stabilized at room temperature by NO3‒, heating and adding a large excess of BF4‒ can expedite cage isomerization via dynamic guest exchange. Ultimately, MOC-35, with better host-guest fitting to BF4‒, will entirely replace the constitutional dynamic library of MOC-35 and MOC-36.
The significant differences in cage size and windows of MOC-35 and MOC-36 could endow them with distinct guest inclusion behaviors [40]. To confirm this, we tested the inclusion of four different aromatic hydrocarbons including phenanthrene-9-carbaldehyde (G1), pyrene-1-carbaldehyde (G2), 4-(diphenylamino)benzaldehyde (G3) and 2,4,5-triphenyl-1H-imidazole (G4) with distinguishable molecular symmetry and aromatic moiety (Fig. 4a).
The study of guest encapsulation was performed in a DMSO-d6/D2O = 2/1 (v/v) mixture (Figs. S62–S97 in Supporting information). For MOC-35 (Figs. S62–S74), the proton signals of the host display remarkable shifts, of which the Py protons Ha and Hd generally move downfield while the Ph protons He and Hf move upfield (Fig. 4b and Fig. S74). All guest signals are up-field shifted, evidently due to a shielding effect of L center toward the encapsulated guests. The association constants corresponding to the interactions between the four guests and MOC-35 cage were estimated by 1H NMR titrations (Fig. 4c) [41]. The relative strong host-guest interacitons with Ka values in the 1279~3893 L/mol range are determined. Formation of G⊂MOC-35 clathrates via fast guest exchange has been further verified by 1H DOSY spectra, which disclose that the diffusion coefficients of the exchanging guests fall in between those of the free guests and the host, showing the weighted average of the coefficients of the free and bound guests [42].
For comparison, MOC-36 has a even larger cavity and open windows, so the guest molecules can undergo much faster guest exchange via the cage windows, thus display weaker binding behavoir with the host. This expection is well supported by the 1H NMR and 1H DOSY measurements (Figs. S75–S87). Upon guest titrations, the protons of the host appear to be less affected, while those of guest molecules show slight chemical shift changes (Fig. 4b). The binding constants of aforementioned guests are determined similarly using Bindfit method (Fig. 4c). The relatively smaller Ka values in the 656~1141 L/mol range indicate even fast exchange behavior of the guests and their weaker binding ability towards MOC-36 than MOC-35, which are further confirmed by the 1H DOSY data with closer diffusion coefficients of the exchanging guests to those of the free guest (Fig. 4c). Such different guest binding behaviors suggest a potential to tune the cage cavities via supramolecular isomerization to meet the demand of separation, catalysis and sensing for varied guests with appreciate kinetics and thermodynamics. It is noteworthy that the cage MOC-34 with small cavity but large windows shows more similar guest encapsulation behavior with MOC-36 than MOC-35, evidented by the relatively small proton signal changes and larger difference in 1H DOSY spectra (Figs. S89–S97).
In summary, we have described self-assembly of three different types of Pd-based metal-organic cages, MOC-34, MOC-35, and MOC-36. The stoichiometric cage transformations from Pd2L4-type MOC-34 to Pd6L8-type MOC-35 or unprecedented Pd9L12-type MOC-36 are well-controlled by anion template induction, while the cage isomerization from MOC-36 to MOC-35 is found to be thermal-driven and significantly affected by dynamic host anion interactions. The experimental and calculation results reveal diversified influence of anion effect to trigger and control kinetics and thermodynamics in cage assembly and conversion processes. The distinguishable guest binding behaviors by virtue of supramolecular cage isomerization have been investigated. This study provides an example that helps to understand the interplay between anion templates and host-anion dynamics in the artificial mimicry of natural anion receptors, which is crucial for the self-assembly and transformation of cage hosts.
Declaration of competing interest
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The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Acknowledgments
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This work was supported by the NKRD Program of China (No. 2021YFA1500401), the National Natural Science Foundation of China (Nos. 21821003, 21890380), and the LIRTP of Guangdong Pearl River Talents Program (No. 2017BT01C161).
Supplementary materials
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Supplementary material associated with this article can be found, in the online version, at doi:10.1016/j.cclet.2023.108477.
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Year 2024 volume 35 Issue 3
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doi: 10.1016/j.cclet.2023.108477
  • Receive Date：2023-02-22
  • Online Date：2025-11-20
  • Published：2024-03-15
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  • Received：2023-02-22
  • Revised：2023-04-11
  • Accepted：2023-04-18
Affiliations
    a MOE Laboratory of Bioinorganic and Synthetic Chemistry, Lehn Institute of Functional Materials, School of Chemistry, Sun Yat-sen University, Guangzhou 510006, China
    b Institute of Environmental Research at Greater Bay Area, Guangzhou University, Guangzhou 510006, China
    c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
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表12种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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