The main focus of this PhD thesis is the synthesis of new water soluble macrocycles (calix[n]arenes, cyclodextrins and pillar[n]arenes) and the investigation of their supramolecular chemistry. After a brief introduction about the principles, perspectives, and recent developments in the field of water-soluble synthetic receptors (Chapter 1) the following sections describe the experimental results of my PhD project. Chapter 2 reports the synthesis and the aggregation properties of new amphiphilic macrocycles based on anionic and neutral p-alkyl-calix[n]arenes and a mono-substituted cationic cyclodextrin by means of different techniques (1D and 2D 1H NMR, DOSY, DLS, AFM, Cryo-Tem) together with different applications in the recognition and/or encapsulation of different substrates. Chapter 3 describes the aggregation features of supramolecular amphiphilic systems (supra-amphiphiles) based on the water soluble p-tert-butylcalix[5]arene-penta-O-4-butylsulfonato and gemini ,-alkanediyldiammonium ions, demonstrating that the aggregation phenomena can be efficiently modulated by changing the length of the spacer in the gemini guest and/or the host-guest ratio. Furthermore, this chapter demonstrated the great potential of calixarene-based supra-amphiphiles in the solubilisation of water insoluble drugs by using as a model the anticancer drug tamoxifen. Chapter 4 provides a fascinating example of social (non integrative) self-sorting based on a four component system consisting of two water-soluble calix[5]arene derivatives differently substituted at the upper rim and two ,-alkanediyldiammonium ions of different lengths (H3N+-(CH2)n-NH3+, n = 8, 10). The obtained results demonstrated that among the ten possible complexes with mixed/different stoichiometry, only two capsular-complexes are formed. Finally, Chapter 5 proposes a potential pillararene (WP5) based drug-transport system where WP5 and the antibiotic drugs amikacin and levofloxacin interact with each other forming stable inclusion complexes in aqueous solution. Furthermore, WP5 was employed for the preparation of layer-by-layer (LbL) thin solid films on glass surfaces loaded with the above mentioned antibiotics, with the ultimate goal of fabricating antibacterial multilayered coatings for controlled drug release.

The supramolecular chemistry of water soluble calixarenes, cyclodextrins and pillararenes.

BARBERA, LUCIA
2017-12-12

Abstract

The main focus of this PhD thesis is the synthesis of new water soluble macrocycles (calix[n]arenes, cyclodextrins and pillar[n]arenes) and the investigation of their supramolecular chemistry. After a brief introduction about the principles, perspectives, and recent developments in the field of water-soluble synthetic receptors (Chapter 1) the following sections describe the experimental results of my PhD project. Chapter 2 reports the synthesis and the aggregation properties of new amphiphilic macrocycles based on anionic and neutral p-alkyl-calix[n]arenes and a mono-substituted cationic cyclodextrin by means of different techniques (1D and 2D 1H NMR, DOSY, DLS, AFM, Cryo-Tem) together with different applications in the recognition and/or encapsulation of different substrates. Chapter 3 describes the aggregation features of supramolecular amphiphilic systems (supra-amphiphiles) based on the water soluble p-tert-butylcalix[5]arene-penta-O-4-butylsulfonato and gemini ,-alkanediyldiammonium ions, demonstrating that the aggregation phenomena can be efficiently modulated by changing the length of the spacer in the gemini guest and/or the host-guest ratio. Furthermore, this chapter demonstrated the great potential of calixarene-based supra-amphiphiles in the solubilisation of water insoluble drugs by using as a model the anticancer drug tamoxifen. Chapter 4 provides a fascinating example of social (non integrative) self-sorting based on a four component system consisting of two water-soluble calix[5]arene derivatives differently substituted at the upper rim and two ,-alkanediyldiammonium ions of different lengths (H3N+-(CH2)n-NH3+, n = 8, 10). The obtained results demonstrated that among the ten possible complexes with mixed/different stoichiometry, only two capsular-complexes are formed. Finally, Chapter 5 proposes a potential pillararene (WP5) based drug-transport system where WP5 and the antibiotic drugs amikacin and levofloxacin interact with each other forming stable inclusion complexes in aqueous solution. Furthermore, WP5 was employed for the preparation of layer-by-layer (LbL) thin solid films on glass surfaces loaded with the above mentioned antibiotics, with the ultimate goal of fabricating antibacterial multilayered coatings for controlled drug release.
12-dic-2017
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Descrizione: The supramolecular chemistry of water soluble calixarenes, cyclodextrins and pillararenes.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11570/3117347
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