In this Doctoral Thesis, through several examples of new chemical modifications characterized by high yields and selectivities and new supramolecular structures, held together by a wide range of intermolecular forces forming several new host systems, we reached our target to revamp triphenylene and derivatives as a new molecular scaffold in supramolecular chemistry. More specifically, the introduction in our triphenylenic scaffold of alkyl thiol chains allowed the formation of sulphide and disulphide covalent cages, while by insertion of pyridine moieties through Mannich reaction it was possible to obtain transition metal coordination cages upon addition of metal corners. The creation of a tris-acid from the original scaffold allowed the investigation of self-aggregation capsules through hydrogen bonds between carboxylic acids, and the functionalization with charged polytails attached to the central triphenylenic core, alternated with apolar substituents, allowed solubilization in water with the formation of very small micelles. Moreover, the interaction between positively charged and negatively charged triphenylenes permitted the creation of peculiar ionic hetero-dimeric capsules. We are sure that this will spur future investigation on the capsules and cages presented in this work, enriching the scientific community involved in this interdisciplinary field of research.
SYNTHESIS OF TRIPHENYLENES FOR SUPRAMOLECULAR APPLICATIONS / Berton, Giacomo. - (2020 Mar 06).
SYNTHESIS OF TRIPHENYLENES FOR SUPRAMOLECULAR APPLICATIONS
BERTON, GIACOMO
2020-03-06
Abstract
In this Doctoral Thesis, through several examples of new chemical modifications characterized by high yields and selectivities and new supramolecular structures, held together by a wide range of intermolecular forces forming several new host systems, we reached our target to revamp triphenylene and derivatives as a new molecular scaffold in supramolecular chemistry. More specifically, the introduction in our triphenylenic scaffold of alkyl thiol chains allowed the formation of sulphide and disulphide covalent cages, while by insertion of pyridine moieties through Mannich reaction it was possible to obtain transition metal coordination cages upon addition of metal corners. The creation of a tris-acid from the original scaffold allowed the investigation of self-aggregation capsules through hydrogen bonds between carboxylic acids, and the functionalization with charged polytails attached to the central triphenylenic core, alternated with apolar substituents, allowed solubilization in water with the formation of very small micelles. Moreover, the interaction between positively charged and negatively charged triphenylenes permitted the creation of peculiar ionic hetero-dimeric capsules. We are sure that this will spur future investigation on the capsules and cages presented in this work, enriching the scientific community involved in this interdisciplinary field of research.File | Dimensione | Formato | |
---|---|---|---|
Tesi PhD Giacomo Berton versione compressa.pdf
Open Access dal 07/03/2021
Descrizione: PhD Thesis Giacomo Berton
Tipologia:
Tesi di dottorato
Dimensione
19.82 MB
Formato
Adobe PDF
|
19.82 MB | Adobe PDF | Visualizza/Apri |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.