Pub Date : 2019-08-28DOI: 10.1039/9781788015950-00001
D. Tuncel
First, in this chapter, smart materials are briefly introduced, followed by a short discussion on the dynamic, reversible stimuli-responsive supramolecular materials. Then the role of the host–guest complexation in the construction of these materials is evaluated in order to position the CB-containing functional materials in the context of smart materials. The chapter also provides a brief outline of the book with a brief rationale on the arrangement of the chapters.
{"title":"Chapter 1. Introduction: Cucurbituril-containing Functional Materials in the Context of Smart Materials","authors":"D. Tuncel","doi":"10.1039/9781788015950-00001","DOIUrl":"https://doi.org/10.1039/9781788015950-00001","url":null,"abstract":"First, in this chapter, smart materials are briefly introduced, followed by a short discussion on the dynamic, reversible stimuli-responsive supramolecular materials. Then the role of the host–guest complexation in the construction of these materials is evaluated in order to position the CB-containing functional materials in the context of smart materials. The chapter also provides a brief outline of the book with a brief rationale on the arrangement of the chapters.","PeriodicalId":222435,"journal":{"name":"Cucurbituril-based Functional Materials","volume":"2 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"122551909","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-08-28DOI: 10.1039/9781788015950-00235
J. Mohanty, Raman Khurana, N. Barooah, A. C. Bhasikuttan
Construction of smart materials based on supramolecular interactions has received considerable research interest owing to their potential applications in energy storage, photonic devices, drug delivery vehicles, sensors as well as therapeutics. In this context, research literature has seen tremendous contributions on the supramolecular assemblies of small guest molecules with various macrocyclic receptors because they provide a unique way to control tailor-made nanoarchitectures in creating predesigned functional materials for targeted applications. This chapter covers some of the recent works, including ours, on the spectacular molecular properties of cucurbituril-based supramolecular functional assemblies of a few organic dyes and polyoxometalates having technological and biological importance, especially in the domain of aqueous dye laser, light-emitting devices, photofunctional devices, energy storage devices, molecular architectures, supramolecular catalysts, radiotracer separation, antibacterial agents and drug delivery vehicles.
{"title":"Chapter 11. Cucurbituril-functionalized Supramolecular Assemblies: Gateways to Diverse Applications","authors":"J. Mohanty, Raman Khurana, N. Barooah, A. C. Bhasikuttan","doi":"10.1039/9781788015950-00235","DOIUrl":"https://doi.org/10.1039/9781788015950-00235","url":null,"abstract":"Construction of smart materials based on supramolecular interactions has received considerable research interest owing to their potential applications in energy storage, photonic devices, drug delivery vehicles, sensors as well as therapeutics. In this context, research literature has seen tremendous contributions on the supramolecular assemblies of small guest molecules with various macrocyclic receptors because they provide a unique way to control tailor-made nanoarchitectures in creating predesigned functional materials for targeted applications. This chapter covers some of the recent works, including ours, on the spectacular molecular properties of cucurbituril-based supramolecular functional assemblies of a few organic dyes and polyoxometalates having technological and biological importance, especially in the domain of aqueous dye laser, light-emitting devices, photofunctional devices, energy storage devices, molecular architectures, supramolecular catalysts, radiotracer separation, antibacterial agents and drug delivery vehicles.","PeriodicalId":222435,"journal":{"name":"Cucurbituril-based Functional Materials","volume":"4 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"131156625","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-08-28DOI: 10.1039/9781788015950-00193
Qian Cheng, H. Yin, Ian W. Wyman, Ruibing Wang
The cucurbit[n]uril (CB[n]) family is an emerging class of host molecules in the field of supramolecular chemistry with a relatively short history (except for CB[6]). The internal cavities of CB[n]s are nonpolar and hydrophobic, guarded by two carbonyl-laced portals, thus they can encapsulate not only neutral molecules via hydrophobic effects but also complex cationic species via ion–dipole interactions. Due to these unique properties, many promising discoveries of supramolecular interactions between CB[n]s and biomolecules and small organic drug molecules have emerged with potential implications in the field of pharmaceutical sciences, which have become one of the most significant areas of potential applications for CB[n]s. In this chapter, we summarize the noncovalent interactions of peptides, proteins and drug molecules with CB[n] homologues and derivatives and discuss the ability of CB[n]s to modulate the functions and bioactivities of these species through host–guest chemistry, as well as the potential of CB[n]s for protein enrichments, together with other relevant topics.
{"title":"Chapter 9. Supramolecular Interactions of Cucurbit[n]uril Homologues and Derivatives with Biomolecules and Drugs","authors":"Qian Cheng, H. Yin, Ian W. Wyman, Ruibing Wang","doi":"10.1039/9781788015950-00193","DOIUrl":"https://doi.org/10.1039/9781788015950-00193","url":null,"abstract":"The cucurbit[n]uril (CB[n]) family is an emerging class of host molecules in the field of supramolecular chemistry with a relatively short history (except for CB[6]). The internal cavities of CB[n]s are nonpolar and hydrophobic, guarded by two carbonyl-laced portals, thus they can encapsulate not only neutral molecules via hydrophobic effects but also complex cationic species via ion–dipole interactions. Due to these unique properties, many promising discoveries of supramolecular interactions between CB[n]s and biomolecules and small organic drug molecules have emerged with potential implications in the field of pharmaceutical sciences, which have become one of the most significant areas of potential applications for CB[n]s. In this chapter, we summarize the noncovalent interactions of peptides, proteins and drug molecules with CB[n] homologues and derivatives and discuss the ability of CB[n]s to modulate the functions and bioactivities of these species through host–guest chemistry, as well as the potential of CB[n]s for protein enrichments, together with other relevant topics.","PeriodicalId":222435,"journal":{"name":"Cucurbituril-based Functional Materials","volume":"15 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"116195848","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-08-28DOI: 10.1039/9781788015950-00175
Hui Wang, Dan‐Wei Zhang, Xin Zhao, Zhanting Li
For many years, studies on the generation of periodic or regular porosity and their properties and functions have been limited to insoluble solid-state materials. Self-assembly provides a straightforward strategy for the construction of water-soluble porous supramolecular organic frameworks (SOFs) from rationally designed rigid multitopic molecular components and cucurbit[8]uril (CB[8]). The process is driven hydrophobically by CB[8]-encapsulation-enhanced dimerization of the aromatic (CEBA) units that are appended to the multitopic molecules. By using this strategy, a variety of two-dimensional honeycomb-shaped, square, and rhombic SOFs have been constructed, some of which exhibit interesting absorption and sensing functions. From tetraphenylmethane- and [Ru(bipy)3]2+-derived precursors, three-dimensional diamondoid and cubic SOFs can also be generated. The diamondoid frameworks have been revealed to be open carriers for in situ loading and delivery of antitumor drugs, whereas [Ru(bipy)3]2+-cored frameworks are good porous photosensitizing materials for the enrichment of anionic polyoxometalate catalysts for new visible light–initiated reduction of proton to hydrogen gas. The progress well demonstrates the CB[8]-based CEBA strategy in constructing advanced water-soluble functional porous materials from symmetric preorganized aromatic precursors.
{"title":"Chapter 8. Cucurbit[8]uril-based 2D and 3D Regular Porous Frameworks","authors":"Hui Wang, Dan‐Wei Zhang, Xin Zhao, Zhanting Li","doi":"10.1039/9781788015950-00175","DOIUrl":"https://doi.org/10.1039/9781788015950-00175","url":null,"abstract":"For many years, studies on the generation of periodic or regular porosity and their properties and functions have been limited to insoluble solid-state materials. Self-assembly provides a straightforward strategy for the construction of water-soluble porous supramolecular organic frameworks (SOFs) from rationally designed rigid multitopic molecular components and cucurbit[8]uril (CB[8]). The process is driven hydrophobically by CB[8]-encapsulation-enhanced dimerization of the aromatic (CEBA) units that are appended to the multitopic molecules. By using this strategy, a variety of two-dimensional honeycomb-shaped, square, and rhombic SOFs have been constructed, some of which exhibit interesting absorption and sensing functions. From tetraphenylmethane- and [Ru(bipy)3]2+-derived precursors, three-dimensional diamondoid and cubic SOFs can also be generated. The diamondoid frameworks have been revealed to be open carriers for in situ loading and delivery of antitumor drugs, whereas [Ru(bipy)3]2+-cored frameworks are good porous photosensitizing materials for the enrichment of anionic polyoxometalate catalysts for new visible light–initiated reduction of proton to hydrogen gas. The progress well demonstrates the CB[8]-based CEBA strategy in constructing advanced water-soluble functional porous materials from symmetric preorganized aromatic precursors.","PeriodicalId":222435,"journal":{"name":"Cucurbituril-based Functional Materials","volume":"41 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"115187271","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-08-28DOI: 10.1039/9781788015950-00007
A. Koc, D. Tuncel
In this chapter, we discuss the syntheses and functionalization of cucurbituril (CB[n]) homologues and derivatives. We begin with a historical background on CB[n] chemistry, from the first known CB[n] homologue, CB[6], to the latest advances in functionalized CB[n] synthesis. Then we elaborate on unsubstituted CB[n] homologues regarding their synthesis, isolation, formation mechanisms, and structural and physical properties. We broadly discuss the synthesis of substituted CB[n] derivatives with various strategies. There are three known methods to synthesize substituted CB[n] from modified precursors: (1) use of substituted glycoluril, (2) use of substituted glycoluril oligomers and (3) use of aldehydes other than formaldehyde. In the last part of the chapter, we give detailed information on the direct functionalization of CB[n]. This part presents the synthesis of multi- and monohydroxylated derivatives via radical oxidation of CB[n] homologues and their further derivatization to reactive groups bearing multi- and monoalkylated CB[n].
{"title":"Chapter 2. Cucurbituril Homologues and Derivatives: Syntheses and Functionalization","authors":"A. Koc, D. Tuncel","doi":"10.1039/9781788015950-00007","DOIUrl":"https://doi.org/10.1039/9781788015950-00007","url":null,"abstract":"In this chapter, we discuss the syntheses and functionalization of cucurbituril (CB[n]) homologues and derivatives. We begin with a historical background on CB[n] chemistry, from the first known CB[n] homologue, CB[6], to the latest advances in functionalized CB[n] synthesis. Then we elaborate on unsubstituted CB[n] homologues regarding their synthesis, isolation, formation mechanisms, and structural and physical properties. We broadly discuss the synthesis of substituted CB[n] derivatives with various strategies. There are three known methods to synthesize substituted CB[n] from modified precursors: (1) use of substituted glycoluril, (2) use of substituted glycoluril oligomers and (3) use of aldehydes other than formaldehyde. In the last part of the chapter, we give detailed information on the direct functionalization of CB[n]. This part presents the synthesis of multi- and monohydroxylated derivatives via radical oxidation of CB[n] homologues and their further derivatization to reactive groups bearing multi- and monoalkylated CB[n].","PeriodicalId":222435,"journal":{"name":"Cucurbituril-based Functional Materials","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"129049345","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-08-28DOI: 10.1039/9781788015950-00120
A. Khaligh, D. Tuncel
Cucurbituril-assisted supramolecular polymeric hydrogels (CB-SPHs), formed by supramolecular cross-linking of polymer chains via directional noncovalent interactions, are a novel class of three-dimensional cross-linked polymeric materials with unique properties including stimuli responsiveness, processability, water-retention ability, biocompatibility, biodegradability, biostability, self-healing and shape-memory abilities. Cucurbit[n]urils (CB[n]) with rigid symmetrical structure and remarkably high binding affinity to guest molecules are commonly used macrocyclic hosts for SPHs. Due to the dynamic CB[n] host–guest interactions, CB-SPHs undergo reversible gel–sol conversion and can effectively change their physicochemical and mechanical properties upon exposure to external stimuli. These aqueous polymeric networks exhibit exceptional advantages in a wide variety of biomedical and industrial applications. This chapter describes the recent achievements in the design, synthesis and properties of CB-SPHs constructed through noncovalent interactions of CB[n] hosts with specific chemical motifs pendant from polymer chains, as well as their applications in various fields such as drug delivery, wound dressing and healing, tissue engineering, diagnostic devices, wood conservation, adhesives, stretchable and wearable electronics, injection and printing substances etc.
{"title":"Chapter 6. Cucurbituril-assisted Supramolecular Polymeric Hydrogels","authors":"A. Khaligh, D. Tuncel","doi":"10.1039/9781788015950-00120","DOIUrl":"https://doi.org/10.1039/9781788015950-00120","url":null,"abstract":"Cucurbituril-assisted supramolecular polymeric hydrogels (CB-SPHs), formed by supramolecular cross-linking of polymer chains via directional noncovalent interactions, are a novel class of three-dimensional cross-linked polymeric materials with unique properties including stimuli responsiveness, processability, water-retention ability, biocompatibility, biodegradability, biostability, self-healing and shape-memory abilities. Cucurbit[n]urils (CB[n]) with rigid symmetrical structure and remarkably high binding affinity to guest molecules are commonly used macrocyclic hosts for SPHs. Due to the dynamic CB[n] host–guest interactions, CB-SPHs undergo reversible gel–sol conversion and can effectively change their physicochemical and mechanical properties upon exposure to external stimuli. These aqueous polymeric networks exhibit exceptional advantages in a wide variety of biomedical and industrial applications. This chapter describes the recent achievements in the design, synthesis and properties of CB-SPHs constructed through noncovalent interactions of CB[n] hosts with specific chemical motifs pendant from polymer chains, as well as their applications in various fields such as drug delivery, wound dressing and healing, tissue engineering, diagnostic devices, wood conservation, adhesives, stretchable and wearable electronics, injection and printing substances etc.","PeriodicalId":222435,"journal":{"name":"Cucurbituril-based Functional Materials","volume":"17 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"123128776","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 1900-01-01DOI: 10.1039/9781788015950-00095
Mhejabeen Sayed, S. Choudhury, H. Pal
{"title":"Chapter 5. Hybrid Supramolecular Assemblies of Cucurbit[n]uril-supported Metal and Other Inorganic Nanoparticles","authors":"Mhejabeen Sayed, S. Choudhury, H. Pal","doi":"10.1039/9781788015950-00095","DOIUrl":"https://doi.org/10.1039/9781788015950-00095","url":null,"abstract":"","PeriodicalId":222435,"journal":{"name":"Cucurbituril-based Functional Materials","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"1900-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"126048184","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 1900-01-01DOI: 10.1039/9781788015950-00056
N. Basílio, U. Pischel
In this chapter, the preparation of cucurbituril-based pseudorotaxanes, rotaxanes and polyrotaxanes is illustrated with selected examples. This includes the notions of self-sorting, which enables the setup of homo- and hetero(pseudo)rotaxanes. The implications of thermodynamic and kinetic control are briefly showcased as well. In the main part, these assemblies are discussed in the context of stimuli-responsive systems, whose supramolecular chemistry and functionality can be controlled by using chemical inputs (pH, ions), redox signals or light. In the final part, some applications, such as drug delivery or molecular information processing, are highlighted.
{"title":"Chapter 4. Rotaxanes and Polyrotaxanes","authors":"N. Basílio, U. Pischel","doi":"10.1039/9781788015950-00056","DOIUrl":"https://doi.org/10.1039/9781788015950-00056","url":null,"abstract":"In this chapter, the preparation of cucurbituril-based pseudorotaxanes, rotaxanes and polyrotaxanes is illustrated with selected examples. This includes the notions of self-sorting, which enables the setup of homo- and hetero(pseudo)rotaxanes. The implications of thermodynamic and kinetic control are briefly showcased as well. In the main part, these assemblies are discussed in the context of stimuli-responsive systems, whose supramolecular chemistry and functionality can be controlled by using chemical inputs (pH, ions), redox signals or light. In the final part, some applications, such as drug delivery or molecular information processing, are highlighted.","PeriodicalId":222435,"journal":{"name":"Cucurbituril-based Functional Materials","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"1900-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"129486962","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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