Editorial: Host-Guest Chemistry of Macrocycles

Editorial on the Research Topic
Host-Guest Chemistry of Macrocycles

Macrocycle-based host–guest chemistry has played an important role in the development of supramolecular chemistry. Burgeoning progress has been continuously made in the development of supramolecular assemblies by using various host molecules, such as cyclodextrins (Li and Purdy, 1992Szejtli, 1998Harada et al., 20092014Antoniuk and Amiel, 2016), cucurbiturils (Lagona et al., 2005Ni et al., 2014Barrow et al., 2015Murray et al., 2017), calixarenes (Shinkai et al., 1984Böhmer, 1995Guo and Liu, 2014), crown ethers (Pedersen, 1967Amabilino et al., 1995Zhang et al., 2007Xiao et al., 2020a2021), pillararenes (Ogoshi et al., 200820162018Xue et al., 2012Strutt et al., 2014Kakuta and Yamagishi, 2018Xiao et al., 20182019a,b,c), and other macrocycles (Wang et al., 2019). The architectures and properties of different hosts endow themselves with versatile abilities to bind with different guest molecules. Therefore, macrocyclic hosts show significant potential in constructing assorted functional materials, such as hydrogels (Appel et al., 2012Xiao et al., 2019d), functional supramolecular polymers (Chen et al., 2019Xiao et al., 2020b), artificial light harvesting systems (Xiao et al., 2019e), and so on.

Supramolecular polymers, a concept combining elements of both supramolecular chemistry and polymer science, are promising dynamic functional materials. Moreover, the incorporation of fluorophores into supramolecular polymers could endow them with interesting photophysical properties. In this context, Zhang et al. reviewed fluorescent supramolecular polymers constructed by crown ether-based host-guest interactions. They focused on fabrication strategies, properties, and potential applications of these materials. On the same Topic, Wu and Xiao contributed an article on an aggregation induced emissive (AIE) supramolecular polymer which was constructed from a cyanostilbene based ditopic benzo-21-crown-7 and a ditopic dialkylammonium salt. In another review paper, Gatiatulin et al. summarized the possible alternatives to the classical key-to-lock principle with higher selectivity for molecular recognition. These alternatives are based on cooperativity of phase transitions, which adds up the small differences in molecular structure of different bound guests. In a minireview, Duan et al. (b) summarized broad approaches for the preparation of graphene nanomaterials functionalized with calix[n]arene/pillar[n]arene, and their applications in molecular recognition, fluorescent sensors, electrochemical biosensors, and as catalytic, antibacterial, and adsorption materials.

Calixarene derivatives have played an important role in developing anti-tumor agents. The contribution of An et al. focused on novel dihomooxacalix[4]arene-based anti-tumor agents. In their work, they reported the synthesis of 19 structurally related dihomooxacalix[4]arene amide derivatives in search of optimal efficacy. Guo et al. synthesized a p-tert-butyldihomooxacalix[4]arene, which could form a soft gel in cyclohexane. Moreover, the xerogel with its highly interconnected and homogeneous porous network, may be used for drug storage and controlled release. Pillararenes are a relatively new macrocyclic host and have been employed to fabricate various supramolecular materials. Macrocyclic amphiphiles have attracted much attention due to their unique properties in the construction of functional nanomaterials. The work of Wang et al. investigates a pillararene-based macrocyclic amphiphile, which is responsive to pH. Interestingly, a pH-induced transition between single-chain macrocyclic amphiphile and bola-type amphiphile and the corresponding self-assembly behavior was investigated. Self-assembled peptides can also be used to fabricate new biomaterials for medical applications. Duan et al. (a) developed cationic pillar[6]arene-modified graphene films on glassy carbon electrodes directly from graphene oxide-cationic pillar[6]arene dispersions using a pulsed electrodeposition technique. Experimental results revealed that the electrochemically reduced graphene oxide-cationic pillar[6]arene films could show a much higher electrochemical response to five purine bases than unmodified reduced graphene oxide films and bare glassy carbon electrodes. In other work, Duan, Wang, Zhang et al. designed new host-guest binding motifs based on a water-soluble pillar[6]arene dodecyl-ammonium chloride with two aromatic sulfonic acids in water. Interestingly, both of these host-guest complexes can be tuned reversibly between their complexed and decomplexed states by sequential addition of a base and an acid (NaOH and HCl, respectively). Construction of polypseudorotaxanes in high-polar organic solvents is challenging owing to the weak interactions between macrocycles and axles. Su et al. prepared a novel metal-coordinated poly[2]pseudorotaxane by using pillar[5]arene, 1,4-bis(4-pyridyl pyridinium)butane, and [PdCl2(PhCN)2] in dimethyl sulfoxide.

Chaudhuri et al. developed a method to promote clean and environmentally friendly disinfection of phenolic substrates by employing α-cyclodextrin to affect the product distribution in chlorine dioxide-mediated decomposition of organic pollutants. Chen et al. synthesized and characterized two novel cyclic γ-peptides with hydrophobic inner surfaces, which could self-assemble into stacking nanotubes through intermolecular H-bonds and π-π interactions. Notably, the nanotubes could serve as selective water channels to transport water across the lipid membrane. Metallacycles have obtained great interest in recent years. The contribution of Wu et al. constructed two porphyrin-based organoplatinum(II) metallacycles through coordination-driven self-assembly. Interestingly, these metallacycles could be utilized as catalysts for photo-oxidization with high efficiency. Zhu et al. demonstrated a simple protocol to prepare stimuli-responsive surface-active microcrystalline cellulose particles which are able to reversibly self-assemble at a fluid interface via reversible in situ hydrophobization to stabilize stimuli-responsive Pickering emulsions.

In summary, this Research Topic has highlighted how the fields of macrocyclic and supramolecular chemistry are still inextricably linked. The field has matured considerably in recent years and is now beginning to show more and more potential for real-world applications to address important issues across the sciences.

Author Contributions

All authors listed have made a substantial, direct and intellectual contribution to the work, and approved it for publication.

Conflict of Interest

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

The handling editor declared a past co-authorship with one of the authors RE.

Acknowledgments

We acknowledge financial support by the National Natural Science Foundation of China (21702020, 21801139) and Science Foundation Ireland (SFI) co-funded under the European Regional Development Fund under Grant number 12/RC/2275_P2.

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September 30, 2020