Ultrafast sonochemical synthesis of imine-linked porous organic cages with high surface area for gas adsorption

Abstract

Porous organic cages (POCs) are promising crystalline porous materials with high porosity, but their conventional solvothermal synthesis is time-consuming and energy-intensive. Herein, we report for the first time an ultrafast sonochemical approach (<5 minutes, ambient temperature) for synthesizing imine-linked POCs (Sono-CC3R-OH, Sono-CC3R, and Sono-NC2R) using methanol as a green solvent. The sonochemically synthesized POCs exhibit exceptional porosity and crystallinity, outperforming their solvothermal counterparts, while achieving a ∼78% reduction in energy consumption. Furthermore, this approach exhibits excellent potential for large-scale production and efficient solvent recyclability. High-surface-area Sono-CC3R-OH demonstrates preferable CO₂ adsorption with a CO₂/N₂ selectivity of up to 77.5. Thus, this work opens a quick and efficient pathway for the synthesis of imine-linked POCs with superior surface area, offering great potential for the scalable production of gas adsorbents.

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New concepts

In this work, we introduce for the first time a sonochemical approach for the ultrafast synthesis of imine-linked porous organic cages (POCs) under ambient conditions. Unlike conventional solvothermal methods that require prolonged reaction times and high energy input, our approach employs high-frequency ultrasound to drive imine condensation in <5 minutes, using methanol as a green and recyclable solvent. The resulting Sono-POCs exhibit exceptional crystallinity and porosity, surpassing solvothermally synthesized counterparts while reducing energy consumption. The key innovation lies in the scalability and solvent reusability of this method, enabling large-scale production with consistent performance over at least five cycles. Notably, Sono-POCs demonstrate superior CO₂/N₂ selectivity, highlighting their potential as efficient gas adsorbents. To our knowledge, this is the first and only technique capable of producing high-quality POCs with such rapid kinetics, energy efficiency, and scalability, opening new avenues for sustainable POC synthesis.

Introduction

Porous organic cages (POCs) are a newly developed class of crystalline porous materials characterized by stable and permanent voids within their rigid molecular structures. These voids are primarily formed through covalent bonds, such as carbon–carbon or carbon–heteroatom (e.g., imines, amides, and boronic esters) interactions.¹ Due to their low density, high porosity, good stability, and tunable structures with customizable functions,^1–4 POCs have garnered great interest in a range of applications, including gas adsorption and separation,^5–8 catalysis,^9,10 photodynamic therapy,¹¹ and capture of environmental pollutants.^12–17 The traditional method for preparing POCs is solvothermal synthesis, which often requires long reaction times (2–7 days), elevated temperatures (90–120 °C), complex procedures and the use of highly toxic organic solvents (such as PhNO₂, PhCl, PhMe and others).^18,19 These limitations have driven the search for alternative synthetic methods. Consequently, various synthetic methods, including the dynamic flow method,²⁰ microwave-assisted approach,²¹ twin screw extrusion method,²² high pressure homogenization,²³ and dynamic solvent-mediated strategy,²⁴ have been investigated for the preparation of POCs. Although these emerging methods present advantages over the traditional solvothermal synthesis, they also suffer from some drawbacks such as the unavoidable use of organic solvents,^20,24 unsafe operating conditions, high energy consumption, high operating costs and complex procedures.^21–23 Therefore, this necessitates the development of a facile and efficient approach to overcome the existing challenges in POC synthesis.

Sonochemical reactions are driven by intense ultrasound waves that generate high-energy conditions in liquid. In sonochemistry, acoustic cavitation plays a pivotal role, occurring when bubbles form, expand, and then rapidly collapse under the influence of ultrasonic shear forces. The collapse of these bubbles generates localized hot spots with extremely high temperatures and pressures, creating a unique environment that significantly accelerates chemical reactions by several orders of magnitude.²⁵ The sonochemical approach has several key advantages, including simple equipment, ease of operation, and low cost. Therefore, it has been widely employed in the preparation of organic small molecules,²⁶ covalent organic frameworks,^27–30 and metal–organic frameworks.^31–35 Unlike traditional methods that require extreme conditions such as high temperatures and pressures, sonochemistry can achieve similar or even superior reaction rates under mild conditions. This simplicity and efficiency make sonochemistry an attractive method for the synthesis of POCs, potentially offering a more practical and cost-effective approach. However, to the best of our knowledge, the application of the sonochemical approach to prepare POCs has not yet been reported, highlighting the need for further exploration in this field.

In this study, we developed, for the first time, a sonochemical approach for the rapid synthesis of imine-linked POCs within an ultra-short time (<5 min). As a proof of concept, three distinct POCs (Sono-CC3R-OH, Sono-CC3R, and Sono-NC2R) were successfully synthesized using this sonochemical approach (Fig. 1). The resulting “Sono-POCs” exhibit superior crystallinity and porosity compared to their solvothermal counterparts (Solvo-POCs). Notably, this approach reduced energy consumption by ∼78% (0.07 kWh vs. 0.33 kWh for solvothermal synthesis), while enabling large-scale production with efficient solvent recyclability. Furthermore, Sono-CC3R-OH demonstrates promising potential for selective CO₂ adsorption, achieving a CO₂/N₂ selectivity of up to 77.5. Our work presents a green, facile and highly efficient approach for the preparation of imine-linked POCs, showcasing its significant potential for large-scale production and practical applications.

Fig. 1 The sonochemical approach for synthesizing POCs. (a) Comparison of the sonochemical approach and solvothermal method (red: aldehydes; blue: amines). (b) The schematic diagram of the synthesis of POCs by the sonochemical approach.

Results and discussion

Synthesis and optimization of Sono-CC3R-OH

As a proof of concept, the well-known imine-linked POC “CC3R-OH” was initially chosen as the model. This material was synthesized through the condensation of 2-hydroxy-1,3,5-benzenetricarbaldehyde and (1R,2R)-(−)-1,2-diaminocyclohexane (Fig. 2a). To gain a better understanding of the formation of Sono-POCs, we first investigated the effects of solvent volume on the material's crystallinity, porosity, and yield. The amounts of aldehyde and amine were kept constant, with an aldehyde-to-amine ratio of 2 : 3, while the volumes of methanol were varied to 5 mL, 10 mL, 15 mL, and 20 mL. The ultrasonication time was fixed at 5 min. The successful synthesis of Sono-CC3R-OH was confirmed by powder X-ray diffraction (PXRD) and Fourier-transform infrared (FTIR) spectroscopy. The PXRD patterns of Sono-CC3R-OH exhibited excellent agreement with the simulated structure (Fig. 2b), while FTIR analysis revealed the disappearance of the N–H stretching band (3100–3300 cm⁻¹, corresponding to free amine groups, Fig. 2c) and the appearance of the C=N stretching band (1640–1690 cm⁻¹). These features are consistent with the previously reported characteristics of CC3R-OH synthesized via the solvothermal method,³⁶ thereby demonstrating the feasibility of the sonochemical approach for POC synthesis. Furthermore, the crystallinity of the samples exhibited a positive correlation with the methanol volume, as evidenced by the gradual enhancement of diffraction peak intensities in XRD patterns (Fig. 2b). The BET results showed that as the methanol volume increased, the specific surface area of Sono-CC3R-OH increased sequentially (Fig. 2d). This trend indicates that the larger solvent volume could reduce the concentration of reactants, which may allow for more efficient growth of the porous network, thus contributing to an increase in the specific surface area of the material. However, the yield rapidly declined from 70% to 35% with the methanol volume increasing from 5 mL to 20 mL (Fig. 2e), which is attributed to the decreased probability of molecular collisions and reduced availability of reactants in more dilute solutions, ultimately decreasing the formation rate of the desired product.

Fig. 2 Systematic investigation of the effects of methanol volume on Sono-CC3R-OH formation: (a) synthetic route for Sono-CC3R-OH, (b) PXRD patterns, (c) FTIR spectra, (d) N₂ adsorption isotherms, and (e) the yields of Sono-CC3R-OH at different methanol volumes.

In addition to the effects of solvent volume, ultrasonication time is another critical parameter governing product quality. To obtain POCs with a high surface area, a methanol volume of 20 mL was selected for further optimization of ultrasonication time, while keeping the other parameters constant. Ultrasonication was performed for 1, 5, 10, 30, 60, and 90 min, respectively. PXRD analysis (Fig. 3a) indicated that Sono-CC3R-OH exhibited good crystallinity even after 1 min of ultrasonication, and FTIR also confirmed the successful formation of Sono-CC3R-OH (Fig. 3b). The BET results (Fig. 3c) demonstrated that an optimal surface area of 597 m² g⁻¹ was obtained after 5 min of ultrasonication. It is worth noting that the BET value dropped to its lowest value (86 m² g⁻¹) after 10 min of ultrasonication. This phenomenon can be attributed to the discrete crystalline nature of POCs, where pores consist of cavities within the cages and interconnected accumulation voids.^37,38 At this point, the decrease in BET surface area is likely due to cage aggregation. However, with prolonged ultrasonication (beyond 30 min), rearrangement between cages may occur, leading to an increase in the BET surface area. Furthermore, the effect of ultrasonication time on product yield was also investigated (Fig. 3d). For ultrasonication durations ranging from 1 to 30 min, the yield remained stable at approximately 42–52%. However, when the ultrasonication time exceeded 60 min, a significant increase in yield was observed. Taking into account factors such as time efficiency, energy consumption, and surface area, 5 min was identified as the optimal ultrasonication time.

Fig. 3 Systematic investigation of the effects of reaction time on Sono-CC3R-OH formation: (a) PXRD patterns, (b) FTIR spectra, (c) N₂ adsorption isotherms, and (d) the yields of Sono-CC3R-OH at different reaction times.

Scanning electron microscopy (SEM) images revealed that both Sono-CC3R-OH and Solvo-CC3R-OH share an identical octahedral morphology (Fig. S1a and b, ESI†). Thermogravimetric analysis (TGA) further demonstrated that Sono-CC3R-OH possessed high thermal stability, remaining stable up to approximately 350 °C (Fig. S2, ESI†). Control experiments confirmed that water as a solvent is unsuitable for producing CC3R-OH (Fig. S3, ESI†), highlighting the necessity of organic solvents for the formation of high-quality POCs. Notably, Sono-CC3R-OH achieved superior porosity after just 5 min of ultrasonication, significantly surpassing the previously reported shortest synthesis time of 4 h via the ethanol reflux method.³⁹ These findings highlight the exceptional efficiency and advantages of the sonochemical approach for the synthesis of imine-linked POCs.

Universality of the sonochemical approach

To validate the universality of the sonochemical approach for the preparation of imine-linked POCs, we successfully extended this approach to synthesize other well-known imine-linked POCs (Fig. S4–S10, ESI†). Specifically, Sono-CC3R was obtained by reacting 1,3,5-benzenetricarboxaldehyde and (1R,2R)-(−)-1,2-diaminocyclohexane,⁴⁰ while Sono-NC2R was prepared from bis(4-hydroxy-3,5-diformylphenyl)methane and (1R,2R)-(−)-1,2-diaminocyclohexane⁴¹ (Fig. 1b). All POCs were synthesized using the optimized sonochemical procedure and characterized by XRD, FTIR, SEM, TGA, and N₂ adsorption measurements. The resulting products exhibited excellent crystallinity. Among them, Sono-CC3R displayed superior crystallinity across varying methanol volumes, with FTIR spectra confirming the successful formation of CC3R. N₂ adsorption tests showed a larger BET value of 442 m² g⁻¹ when synthesized with 10 mL methanol under 5-min sonication (Fig. S4 and S5, ESI†). TGA further confirmed the excellent thermal stability of Sono-CC3R up to 350 °C (Fig. S6, ESI†). SEM images indicated that both the obtained Sono-CC3R and Solvo-CC3R exhibited similar octahedral morphology (Fig. S7a and b, ESI†). Similarly, Sono-NC2R showed a larger BET value of 138 m² g⁻¹ under identical synthesis conditions (Fig. S8 and S9, ESI†), significantly surpassing both the literature-reported value (3.69 m² g⁻¹)⁴¹ and the experimentally measured BET value for conventionally synthesized NC2R (Fig. S10, ESI†). Furthermore, the TGA analysis demonstrated that Sono-NC2R is thermally stable up to ∼250 °C (Fig. S11, ESI†), with SEM images confirming consistent elongated morphologies for both Sono-NC2R and Solvo-NC2R (Fig. S7c and d, ESI†). In conclusion, all of the above analyses confirm the feasibility of the sonochemical approach for the synthesis of POCs.

For a more extensive verification, we also synthesized two additional imine-linked organic cages by the sonochemical approach: CPOC-201 and CPOC-301.¹⁹ Sono-CPOC-201 was synthesized using 4-connected bowl-shaped tetraformylresorcin-[4]arene (C4RACHO) and m-phenylenediamine. Sono-CPOC-301 was synthesized using C4RACHO and p-phenylenediamine. We found that both Sono-CPOC-201 and Sono-CPOC-301 exhibited good crystallinity (Fig. S12a and d, ESI†) after just 5 min of ultrasonication in 10 mL methanol solution. The FTIR spectra were also consistent with literature data (Fig. S12b and e, ESI†).²⁵ These results further support the versatility of the sonochemical method in synthesizing diverse imine-linked POCs.

To further explore the scope of this approach, we attempted to synthesize hydrazone-linked (C=N–N) POCs using the sonochemical method. However, due to the lower nucleophilicity and basicity of the hydrazone group (–N–NH) compared to amines (–NH₂),^15,42–44 the formation of hydrazone-linked cages proved challenging under ultrasonication. This suggests that while sonochemistry is highly effective for imine-linked POCs, alternative strategies may be required for other dynamic covalent linkages.

Advantages and applications of Sono-POCs

The advantages of the sonochemical approach were evidenced through direct comparison of porosity and energy consumption between Sono-POCs and Solvo-POCs. As shown in Fig. 4a–c, all Sono-POCs exhibited higher BET surface areas than those of Solvo-POCs, indicating that the sonochemical approach can effectively enhance framework porosity. This can be attributed to more uniform ligand interactions under sonochemical conditions, which significantly accelerate the reaction kinetics. Furthermore, the energy consumption for the preparation of Sono-POCs was quantified using an electric power monitor, revealing an exceptionally low value of 0.07 kWh through a 5-minute ultrasonication process at 100% power. In contrast, the conventional solvothermal method consumed 0.33 kWh for a 4-hour process involving heating and stirring at 90 °C under ethanol reflux conditions, making it approximately five times more energy-intensive than the sonochemical approach (Fig. 4d and Fig. S13, ESI†). These findings underscore the remarkable energy efficiency of the sonochemical approach for POC synthesis, highlighting its significant advantages over traditional approaches.

Fig. 4 The comparison of (a)–(c) N₂ adsorption isotherms and (d) energy consumption for Sono-POCs and Solvo-POCs; (e) the PXRD patterns of Sono-CC3R-OH-LS-5 min; and (f) the BET surface area of Sono-CC3R-OH obtained by using the recycled solvent.

It is noteworthy that the sonochemical synthesis approach enables continuous bulk production of POCs by scaling up the amounts of ligand and solvent, named “Sono-CC3R-OH-LS”, thereby paving the way for large-scale production of POCs. In this regard, Sono-CC3R-OH-LS was easily synthesised in 5 min, which still exhibited good crystallinity (Fig. 4e and Fig. S14, ESI†), further highlighting the industrialization potential of the sonochemical synthesis approach. Moreover, the solvent can be easily recycled and reused without any loss of effectiveness in synthesizing subsequent batches of POC materials. This was verified by the presence of similar PXRD peaks and the retention of BET surface areas for Sono-CC3R-OH even after five cycles of solvent recycling (Fig. 4f and Fig. S15, ESI†). In summary, sonochemical synthesis is undoubtedly a highly efficient strategy for the large-scale production of high-performance POCs.

To investigate the gas adsorption and separation performance of Sono-POCs, single component adsorption isotherms of Sono-CC3R-OH for CO₂ and N₂ were measured at 298 K and at 1 bar (Fig. 5a). The sample exhibited preferable CO₂ adsorption with an uptake capacity of 47 cm³ g⁻¹. In addition, ideal adsorbed solution theory (IAST) was employed to evaluate the adsorption selectivity (S_ads) of Sono-CC3R-OH for CO₂/N₂ (v/v = 15/85), which demonstrated an impressive selectivity peaking at 276.95 at low pressure and 77.5 at 1 bar, respectively (Fig. 5b, Fig. S16 and Table S1, ESI†), indicating its potential for selective CO₂ capture. In addition, we conducted a comparative evaluation of the performance of Solvo-CC3R-OH in gas adsorption and separation, which exhibited a lower CO₂ uptake capacity of 35 cm³ g⁻¹ at 298 K and 1 bar, and reduced CO₂/N₂ selectivity values of 88.97 (low pressure) and 60.62 (1 bar) (Fig. S17, ESI†). Our findings demonstrate that the sonochemical approach offers significant potential for both practical POC production and high-performance gas adsorption/separation applications.

Fig. 5 (a) Comparison of the experimental CO₂ and N₂ adsorption isotherms of Sono-CC3R-OH at 298 K. (b) IAST selectivity of CO₂/N₂ mixtures for Sono-CC3R-OH at 298 K.

Conclusions

In summary, we develop for the first time a sonochemical synthesis approach for the preparation of high-performance crystalline POCs, which offers remarkable advantages in terms of simplicity, rapidity, environmental friendliness, scalability, and cost-effectiveness. As a representative demonstration, three imine-linked POCs (Sono-CC3R-OH, Sono-CC3R, and Sono-NC2R) were successfully synthesized at room temperature within 5 minutes using methanol as the sole solvent. The obtained Sono-POCs exhibited excellent crystallinity and abundant porosity, which are superior to those prepared by traditional solvothermal methods. In contrast to the traditional solvothermal method, the sonochemical approach significantly reduces the reaction time and enables the synthesis of POCs under ambient conditions, effectively addressing the inherent limitations of traditional methods, such as high energy consumption and complex preparation procedures. Furthermore, the universality of the sonochemical approach and its potential for large-scale POC synthesis highlight its broad applicability. This green, facile and efficient synthesis approach represents a significant advancement in the field of POC preparation. We anticipate that this approach will not only complement existing synthesis methods for POC synthesis, but also provide promising potential for the scalable production of gas adsorbents.

Author contributions

All authors have approved the final version of the manuscript.

Conflicts of interest

There are no conflicts to declare.

Data availability

The data that support the findings of this study are available in the ESI† and from the corresponding author upon request.

Acknowledgements

This work was supported by the National Key R&D Program of China (2022YFA1503301), the National Natural Science Foundation of China (No. 22471131, 22478204 and 22035003), the Natural Science Foundation of Tianjin (23JCQNJC01400), the Fundamental Research Funds for the Central Universities (Nankai University), the Haihe Laboratory of Sustainable Chemical Transformations (YYJC202101), the Postdoctoral Fellowship Program of CPSF under Grant Number GZC20240774, and the start-up funding of Inner Mongolia University (10000-23112101/183).

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Footnote

† Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d5mh00754b

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