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Controlled Growth of MOFs in Emulsion

Xiaozhu Zhao , Wen Li , Xuerui Zhao , Naipu He , Chao Li , Xuehui Zhang

Progress in Chemistry ›› 2023, Vol. 35 ›› Issue (1) : 157 -167.

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Progress in Chemistry ›› 2023, Vol. 35 ›› Issue (1) : 157-167 DOI: 10.7536/PC220628
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Controlled Growth of MOFs in Emulsion
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Abstract

Metal organic frameworks (MOFs), which are formed by self-assembly of metal ions and organic ligands, are porous crystal materials with controllable morphology. Meanwhile, the emulsification of surfactants plays a key role in the formation of emulsion. The morphologies of micelles by self-assembly of surfactant controls the final morphology of the target materials. Therefore, micelles in emulsion are employed as reaction templates to modulate the morphology of MOFs. In the current review, the formation mechanism and characteristics of traditional emulsion, inverse microemulsion, surfactant-free emulsion and Pickering emulsion are briefly introduced. The progress in controllable growth of MOFs in emulsions is reviewed in detail. In particular, it is an ideal strategy for constructing MOFs composites by using surfactant-free emulsion method and Pickering emulsion method.

Contents

1 Introduction

2 Controllable growths of MOFs in traditional emulsions

3 Controllable growths of MOFs in inverse micro emulsion

4 Controllable growths of MOFs in surfactant-free emulsion

5 Controllable growths of MOFs in Pickering emulsion

6 Conclusion and outlook

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Keywords

metal organic frameworks / controllable morphology / traditional emulsion / inverse micro-emulsion / surfactant-free emulsion / Pickering emulsion

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Xiaozhu Zhao, Wen Li, Xuerui Zhao, Naipu He, Chao Li, Xuehui Zhang. Controlled Growth of MOFs in Emulsion. Progress in Chemistry, 2023, 35(1): 157-167 DOI:10.7536/PC220628

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1 Introduction

In the past two decades, Metal organic frameworks (MOFs), which are porous crystalline materials composed of Metal ions and organic ligands with periodic network structure, have attracted great interest of scientists in the field of materials science. Compared with traditional nanocarriers (such as inorganic zeolites and nanoscale silica), MOFs have the advantages of diverse chemical composition, easily controllable pore size and larger specific surface area, which are widely used in gas storage, adsorption and separation, electrocatalysis, sensors and drug delivery[1][2][3][4][5].
The physicochemical properties exhibited by MOFs are closely related to the size, structure, and shape of their crystalline particles. The nucleation and growth of MOFs are generally affected by coordination regulation, preparation methods and other factors[6,7]. It is an important strategy to effectively control the crystal morphology of MOFs by adding modifiers (monodentate ligands, etc.) to the system to regulate crystal nucleation and growth[8].
In addition, the use of appropriate preparation methods is another important strategy to effectively regulate the nucleation and growth of MOFs crystals. At present, methods such as microwave-assisted synthesis, ultrasound-assisted synthesis, mechanical drying, solvothermal or hydrothermal methods, microfluidic technology, spray drying and emulsion synthesis have been used in the preparation of MOFs[9][10][11][12,13][14][15][16,17]. Among them, the emulsion synthesis method is simple and easy to operate, which can be used to prepare nano-MOFs in large scale under mild laboratory conditions[18]. In addition, by using the emulsion synthesis method, the synthesis process of MOFs crystals is not easy to agglomerate, which is beneficial to the dissipation of reaction heat, and at the same time, it is helpful to control the particle size and morphology of MOFs in the nanometer range[19].
The key to the formation of emulsion is the emulsification of surfactant, and the formed micelles act as a microreactor and play a template role, thus realizing the regulation of microstructure. Surfactant is composed of hydrophilic group and lipophilic group. In traditional emulsion, surfactant assembles into typical oil-in-water micelles in the aqueous phase (continuous phase). With the increase of surfactant concentration, spherical micelles, cylindrical micelles and multi-level two-dimensional or three-dimensional micelles are formed in turn. At present, traditional emulsion, inverse microemulsion, soap-free emulsion and Pickering emulsion can be constructed by adjusting the type and concentration of continuous phase, dispersed phase and emulsifier. MOFs are highly ordered porous crystals formed by self-assembly of metal ions and organic ligands through coordination bonds, and the template effect of micelles in emulsion can effectively control their morphology (Table 1). In this paper, the formation mechanism and characteristics of traditional emulsion, inverse microemulsion, soap-free emulsion and Pickering emulsion are briefly summarized, and the growth and morphology control of MOFs in the above emulsions are emphatically introduced.

2 Controlled growth of MOFs in conventional emulsions.

In traditional emulsions, the surfactant assembles into typical oil-in-water (O/W) micelles in the aqueous phase (continuous phase), and the oil phase is dispersed in the continuous phase to form uniform droplets.
The water-oil interface of O/W micelles formed by traditional emulsions can be used as a template for the growth of MOFs to prepare hollow MOFs (Figure 1)[20⇓~22]. By adjusting the parameters such as solvent properties, surfactants, additives, and temperature, which affect the O/W interfacial tension, MOFs particles with tunable structure, size, and specific surface area can be obtained[23]. In 2008, Qiu et al. Used the emulsion template method to add cetyltrimethylammonium bromide (CTAB) into the HKUST-1 mixture formed by solvothermal. The surfactant self-assembled to form micelles at the water-oil interface, and metal ions and organic ligands reacted at the micellar interface to form a series of porous MOFs with adjustable pore size[24]. The mesoporous walls of MOFs crystals are composed of nano-MOFs assembled by metal ions and organic ligands, and the pore size of these microporous and mesoporous MOFs can be adjusted in the range of 3. 8 ~ 31.0 nm by adjusting the surfactant concentration. 1,3,5-trimethylbenzene (TMB) was used as an auxiliary structure-directing agent of CTAB micelles to adjust the mesopore size of MOFs. The mesopore size of MOFs can be increased by adding TMB in the hydrophobic region of micelles. Selecting the appropriate surfactant and adjusting the surfactant concentration can be used to systematically control the porosity of MOFs. Wee et al. Successfully synthesized a special HKUST-1 material with a regular mesoporous structure of 5 nm using a Keggin-type phosphotungstate (HPW) and CTAB dual-template method, and these mesopores were separated by uniform microporous nano-MOFs[25]. CTAB in the dual template guides the structural units of MOFs to form ordered mesoporous structures, while Keggin ions serve as molecular templates to adjust the structural motifs of MOFs. This MOFs structure showed excellent catalytic activity for the oxidative alcoholysis of styrene under mild reaction conditions. CTAB was removed by Soxhlet extraction with ethanol for 48 H. Sun et al. Designed a synergistic template system composed of CTAB and citric acid (CA), and prepared three-dimensional hierarchical porous MOFs (Figure 2b) containing micropores connected with mesopores, whose mesoporous walls are composed of the microporous skeleton of nano-MOFs[26]. Citric acid can adjust the interaction between CTAB and MOFs precursor through electrostatic interaction and coordination with metal ions (Figure 2a), and the template can be removed by ion exchange for 24 H.
The emulsion template method is not suitable for metal ions and organic ligands with strong crystallization tendency, and whether the cooperative self-assembly between surfactants and MOFs precursors can generate micro/mesoporous MOFs strongly depends on the interfacial interaction between the polar segments of amphiphiles and inorganic ions[27]. Li et al. Proposed that ligands containing both strong and weak coordination should be selected when using the micellar template method to prepare mesoporous MOFs[28]. Strong coordination sites coordinate with metal ions to assemble the framework wall of mesoporous MOFs, while weak coordination sites are difficult to coordinate with metal ions, which may induce surfactants to affect the lattice stability and enhance the cooperative self-assembly ability.
5-Hydroxyisophthalic acid (5-OH-BDC) containing carboxyl and hydroxyl coordination sites was chosen as an organic ligand to coordinate with Cu2+ at the micelle interface formed by cetyltrimethylammonium chloride (CTAC), and a series of highly ordered hexagonal mesoporous MOFs were prepared. Micro-/mesoporous MOFs with controllable morphologies can be effectively prepared by selecting different surfactants as micellar templates, and coordinating metal ions and organic ligands at the micellar interface.During this process, the co-assembly of the micellar template and the MOFs precursor is balanced by adjusting the reaction kinetic parameters to prevent premature phase separation, which affects the subsequent synthesis.

3 Controlled Growth of MOFs in Reverse Microemulsion

Reverse microemulsion is a transparent/semitransparent thermodynamically stable reverse micellar system. Under the action of surfactant, the continuous oil phase encapsulates the nano-sized "micro-water core" to form a water-in-oil (W/O) microemulsion system[29]. Aqueous solution droplets are surrounded by a monolayer interface composed of a surfactant and a cosurfactant to form microemulsion particles, the size of which can be controlled between a few nanometers and tens of nanometers, forming a "microreactor" with extremely small scale and separated from each other.
The water phase in the reverse microemulsion is like a nano-microreactor uniformly distributed in the oil phase, and metal ions and organic ligands are introduced into the nano-reactor of the water-in-oil emulsion,The micelles are collisionally bound by Brownian motion or the organic ligand dissolved in the organic phase enters the micelle through the long-chain alkyl group and coordinates with the metal ion to form MOFs (Fig. 3). The solid phase is precipitated from the microemulsion, so that the processes of nucleation, growth, and agglomeration are confined within a tiny micellar droplet. By adjusting various parameters (i.e., pH value, emulsion mixing time, concentration ratio of metal ion and organic ligand, oil/water ratio, type and amount of surfactant), and taking advantage of the size restriction effect of micelles, MOFs with controllable size and morphology can be prepared. The key of this method is that each droplet containing reactants is surrounded by a continuous oil phase, and the interfacial template composed of surfactants can effectively control the size of particles[30,31].
Lin et al. Synthesized nano-metal-organic frameworks (Gd(BDC)1.5(H2O)2) centered on Gd3+ in CTAB/isooctane/1-hexanol/water system by reverse microemulsion method, which were uniform nanorods, and their morphology and size were affected by the w value (water/surfactant molar ratio) in the microemulsion system. For example, when w = 5 and the concentration of Gd3+ is 50 mmol/L, the nanorods are 100 – 125 nm in length and 40 nm in diameter. When w = 10, nanorods with a length of 1 ~ 2 μm and a diameter of about 100 nm can be obtained under the same conditions. Morphologically controlled Mn-MOFs nanorods were synthesized in a CTAB/1-hexanol/n-heptane/water microemulsion system[32,33]. The Mn(BDC)(H2O)2 is rod-shaped with a diameter of 50 ~ 100 nm and a length of 750 nm. The Mn3(BTC)2(H2O)6 were prepared in CTAB/1-hexanol/isooctane/water microemulsions, and were helical rods with diameters of 50 – 100 nm and lengths of 1 – 2 μm.
Zhai et al. Used reverse microemulsion to prepare ZIF-8 and ZIF-67 in CTAB/n-hexanol/n-heptane/water system, and the obtained MOFs were extremely small in size, in which the average particle size of ZIF-8 was 2.25 nm, the specific surface area was 1402.3 m2/g, and the micropore volume was 0.565 cc/G; the average particle size of ZIF-67 was 2.66 nm, the specific surface area was 1371.3 m2/g, and the micropore volume was 0.465 cc/G[34]. The specific surface area and porosity of MOFs were improved by reverse microemulsion method. Spherical ZIF-8 nanocrystals with high crystallinity and uniform shape and size were successfully prepared in CTAB/n-butanol/n-octane/water reverse microemulsion[35]. In 2021, our research group constructed a reverse microemulsion with CTAB/n-hexanol/n-heptane/water to prepare a lamellar ZIF-8 @ PDMPMA composite, and the carbon dioxide adsorption capacity of the composite was increased by 180% compared with that of pure ZIF-8[36].
In addition, the construction of Ionic liquid reverse microemulsion (Ionic liquid reverse microemulsion ILRMEs) by using ionic liquids instead of traditional organic solvents has also been widely studied in recent years[37]. Nano-ZIF-8 and ZIF-67 with controllable size, extremely small particle size (not more than 2.3 nm), narrow distribution (less than 0.5 nm) and good thermal stability were successfully synthesized in the ionic liquid reverse microemulsion composed of water/TX-100/BmimPF6 (ILME-1) (Fig. 4A). In the water/ethanol/TX-100/BmimPF6 (ILME-2) system, HKUST-1 with similar nanosize was successfully synthesized (Fig. 4 B)[38]. After the formation of MOFs, the ionic liquid phase was collected by syringe, and then the water was removed by vacuum evaporation. When Bai et al studied the ionic liquid microemulsion system, they found that the water content also had a great influence on the structure of the microemulsion in the non-aqueous system[39]. Water can not only form hydrogen bonds, but also hydrate the hydrophilic groups of polar organic solvents and surfactants, which affects the composition parameters of reverse microemulsion and ultimately affects the particle morphology.
Adjusting the oil-water ratio in the microemulsion can change the microstructure of the emulsion, and then control the morphology of MOFs[40]. In 2013, Han et al. Prepared a series of La-MOFs from lanthanum nitrate and 1,3,5-benzenetricarboxylic acid (BTC) in a W/bmimPF6/TX-100 ionic liquid microemulsion system (Fig. 5)[41]. In the W/bmimPF6/TX-100 system, the W/bmimPF6 bicontinuous phase, and the bmimPF6/W microemulsion, the dispersed droplets are spherical, lamellar, and cylindrical, respectively. The morphologies of the La-MOFs synthesized in these microemulsions are basically consistent with the shapes of the dispersed droplets in the corresponding microemulsions. The template and bmimPF6 were removed by washing three times with ethanol and acetone solution (V/V = 1:1).

4 Controlled Growth of MOFs in Soap-free Emulsion

Soap-free emulsion refers to an emulsion system in which no emulsifier is intentionally added to the emulsion or only a small amount of surfactant (concentration below the CMC value) is contained. Amphiphilic polymers can self-assemble into nanomicelles with a wide range of structures (spherical, rod-like, hexagonal, cubic, and lamellar) in liquid phase[42]. As shown in Figure 6, the amphiphilic polymer forms micelles in the soap-free emulsion, which can be used as a template to regulate the nucleation and growth of MOFs, and can also coat MOFs to form polymer/MOFs nanocomposites.
Polyvinylpyrrolidone (PVP) and polyvinyl alcohol (PVA) are typical water-soluble amphiphilic polymers, which can effectively improve the stability of the reaction system in the synthesis of MOFs. As shown in Fig. 7 A, water/1-octanol nanoemulsion was constructed with PVP as emulsifier. The PVP micelle was used as a temporary spherical template, and the zinc ion in the aqueous phase was coordinated with 2-methylimidazole in 1-octanol at the interface of the emulsified droplet to synthesize ZIF-8 nanocrystals, which were further grown into hollow nanospheres[43]. By controlling the ligand concentration and reaction time, hollow ZIF-8 nanospheres with different shell thicknesses could be obtained (Fig. 7 B). The product was collected by centrifugation and the PVP was removed by multiple washes with water. Hollow MOF nanospheres can also be prepared with polyvinyl alcohol (PVA) as stabilizer[44]. ZIF-8 @ PDMAPMA composite nanoparticles with obvious core-shell structure were successfully prepared by one-pot method using N- (3-dimethylaminopropyl) methacrylamide (DMAPMA) as monomer in our group. The emulsification of monomer and polymer effectively controlled the morphology and particle size of ZIF-8. PDMAPMA was wrapped on the surface of ZIF-8, which effectively improved the hydrophilicity of ZIF-8[45]. The above study provides a new idea for the construction of rigid-flexible MOFs/polymer composites.
In addition, the triblock copolymer is used as a mesostructure template to induce the growth of the pore wall MOF structure, and acetic acid is used as a regulator to regulate the crystal growth. These MOFs nanocrystals are embedded along the organic hydrophilic groups of the triblock copolymer chain to form a crystal wall and synthesize a novel bimodal micro/mesoporous MOFs nanocrystal, which maintains the integrity of the mesoporous structure and effectively regulates the crystal morphology of MOFs[46]. After the formation of MOFs, tetrahydrofuran (THF) can be used to remove the surfactant. Salt-assisted nanoemulsion has excellent versatility as a soft template to guide the self-assembly of MOFs. Li et al. Selected nanoemulsions composed of P123 and F127 block copolymers and hydrophobic fragrances to form MOFs with different morphologies, such as bowl-shaped mesoporous particles, dendritic mesoporous nanospheres, walnut-shaped nanoparticles, wrinkled nanosheets and nanodiscs, by changing the type of fragrances and fine-tuning the feed ratio and oil-water ratio of P123 and F127 with the assistance of Cl O 4 - (Fig. 8)[47]. After the reaction, the surfactant template can be removed by soaking the product in ethanol at 60 ℃ for 2 days.
Biomacromolecules such as proteins, polysaccharides and DNA have also been used to construct soap-free emulsion systems to regulate the controllable growth of MOFs. A novel cross-shaped mesoporous catalase @ ZIF-8 composite was successfully prepared by embedding catalase molecules into standard rhombic dodecahedral ZIF-8 crystals[48]. Controlled growth of ZIF-8 crystals on the surface of chitosan was achieved[49]. DNA-functionalized MOFs were also successfully synthesized[50]. To sum up, the emulsification of amphiphilic polymers plays a key role in the controllable growth of MOFs.

5 Controlled Growth of MOFs in Pickering Emulsion

Pickering emulsion is a stable emulsion formed by replacing traditional emulsifiers with small solid particles with emulsifying function. The solid particles are capable of stabilizing water-in-oil emulsions, oil-in-water emulsions, and emulsions of the composite type[51]. Nanometer solid particle stabilized emulsion can avoid the disadvantages of traditional emulsion, such as large amount of surfactant, instability, difficult removal, biological toxicity and so on. When the emulsion is stable, the atoms on the surface of the nanoparticles lack the connection of adjacent atoms, which makes the diffusion electric double layer at the oil-water interface easier to form, forming a rigid barrier to inhibit the coalescence of colloidal particles and maintaining the high stability of the emulsion[52]. As shown in Fig. 9, MOFs grow around the micelles formed by the self-assembly of small solid particles in Pickering emulsion, and hollow MOFs composites can be obtained due to the template effect of these micelles.
Cellulose nanocrystals (CNCs) were used as a Pickering emulsifier to prepare porous ZIF-8 hollow microspheres coated with CNCs in a Pickering emulsion with an oil-water ratio of 1 ∶ 10. The BET surface area was as high as 1240 m2·g-1,CNCs, which made the microspheres hydrophilic[53]. As shown in Fig. 10, Graphene Oxide (GO) was used as particle emulsifier to disperse on the water-oil interface to form Pickering emulsion, and MOFs grew on the surface of GO to form Cu3(BTC)2/GO composite with good CO2 adsorption performance[54].
The Pickering high internal phase emulsion (HIPE) template method can assemble MOFs particles into three-dimensional (3D) hierarchical pore structures with good performance. In 2016, Zhu et al. Used the HIPE template method with UiO-66 particles as the stabilizer to prepare three-dimensional hierarchical porous MOFs crystals in HIPE[55]. UiO-66 acts as a stabilizer for the only Pickering emulsion in this process. Compared with the traditional HIPE method, the Pickering HIPE template method has the following advantages: (1) The particles at the oil-water interface are irreversibly adsorbed, forming a more stable emulsion. (2) MOFs are synthesized within HIPE, and the interfacial stabilizer particles can functionalize the resulting porous materials.
Porous ZIF-8/polystyrene composites with spherical, columnar and irregular particles were prepared by using nano-MOFs particles as Pickering particle emulsifier, styrene, divinylbenzene (DVB) and oleic acid as the continuous phase[56]. ZIF-8 crystal particles with a particle size of 200 nm were used as Pickering emulsion stabilizers, and ZIF-8 three-dimensional porous crystals were formed by further growth in the continuous phase of O/W Pickering HIPE, and their morphology was affected by the concentration of ZIF-8 crystals and the volume fraction of the dispersed phase (Fig. 11)[57]. The oil absorption rate of the product is very large (reaching equilibrium within 5 s), and the absorption value is 5.5~11.0 mL·g-1. The porous material has a good prospect in oil-water separation and is also a Knoevenagel reaction catalyst. In the method, the ZIF-8 nanocrystal is the only Pickering emulsion stabilizer, participates in the formation of the three-dimensional porous ZIF-8 crystal, avoids other polymers from participating in the reaction, omits the step of removing the template, and is simple to operate.
Anisotropic particles, microcapsules and porous materials can be prepared by Pickering emulsion template method. This method can be used to prepare a large number of MOFs superstructures and better control the pore structure of MOFs, which is of great significance to the transmission of selectivity and catalytic permeability[58].
Therefore, it is not difficult to understand that the template effect of micelles in emulsion can realize the morphology control and controllable growth of MOFs. Taking ZIF-8 as an example, ZIF-8 nanocrystals with a size of less than 100 nm can be obtained in the traditional emulsion, maintaining a high specific surface area of 1360 m2/g[59]. ZIF-8 nanocrystals prepared by the surfactant-mediated method showed faster adsorption kinetics in aqueous solution. In the microemulsion, the particle size of ZIF-8 is very small, and the particle size of ZIF-8 prepared in the ionic microemulsion is even less than 2. 3 nm. As the particle size shrinks to nanoscale, ZIF-8 shows potential applications in catalysis, drug loading, biomedical imaging. With polymer as the template, ZIF-8 has more diverse morphologies, such as cruciform, hollow spheres, etc. Its unique morphology determines its high protein loading capacity. ZIF-8 hierarchical pore superstructure was prepared by Pickering emulsion templating method, and its rich pore structure has potential application value in selective catalysis and gas adsorption.

6 Conclusion and prospect

Metal organic frameworks (MOFs) can be controllably grown in emulsion, and the template effect of emulsifier is the key factor to control the morphology and size of MOFs. By constructing different emulsion systems, metal ions and organic ligands use the micelle as a microreactor to coordinate inside and on the surface of the micelle to form MOFs, and the final morphology depends on the morphology of the micelle and the structure of the surfactant. In the traditional emulsion, metal ions and organic ligands react at the micelle interface to generate porous nano-MOFs with adjustable shell thickness and pore size, and the surfactant acts as a template to construct meso/macropores. Nano-MOFs were prepared in microemulsion, and the morphologies of MOFs were different by adjusting the proportion of each component in the microemulsion region. In reverse microemulsion, nano-MOFs crystals with extremely small size can be prepared. The process of soap-free emulsion synthesis of MOFs is more environmentally friendly, and MOFs materials from zero dimension to three dimensions can be prepared in soap-free emulsion. Pickering emulsion uses solid particles with emulsifying function as stabilizers, and the composite materials of macroporous MOFs and nanoparticles can be prepared around the template. Therefore, the growth of MOFs, including their particle size, morphology and porosity, can be controlled by controlling the reaction conditions and the type and amount of surfactants to construct different emulsion systems.
The morphology control of MOFs prepared in emulsion mainly depends on the micelle template formed by the self-assembly of emulsifiers. Although there is a strong correlation between the micelle template and the morphology of MOFs, different MOFs are extremely dependent on the emulsion environment in the synthesis process. The structural evolution of MOFs in the synthesis process is closely related to the surface structure of MOF nanocrystals. Due to the wide diversity of organic ligands, metal ions and surfactants, the nucleation efficiency of micelles and the nucleation and growth of MOFs are affected by many factors. Therefore, there are still many problems to be solved for the nucleation of MOFs in emulsion and their controlled growth. 1) Emulsion is a kind of multi-component complex system, and its own system stability will further affect the controllable growth of MOFs. Therefore, exploring a stable emulsion system is the key to realize the controllable growth of MOFs in emulsion. 2) In the growth of MOFs in the emulsion system, in addition to the ordered assembly of fixed organic ligands and metal ions, some emulsifiers themselves have coordination with metal ions, so there is competition between emulsifiers and organic ligands and metal ions, which makes it more difficult to control the morphology of MOFs. 3) It is essential to explore the stable and mature preparation technology of MOFs, especially to explore the heterogeneous nucleation and controllable growth mechanism of MOFs. Although the controllable growth of MOFs in emulsion system has the above problems, we believe that the use of emulsion system is one of the effective strategies to achieve the controllable growth of MOFs, especially the soap-free emulsion method and Pickering emulsion method are important methods to construct MOFs composites.

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Funding

Science and Technology Programs of Gansu Province(20YF8GA032)

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