| Supramolecular chemistry has the potential to take traditional organic chemistry to a new level through self-assembly, making it possible to design dynamic, nanosized supramolecules otherwise inaccessible through covalent synthesis. Specifically, our group has contributed through the discovery and in-depth study of variations of the 8-(meta-carbonylphenyl)-2'-deoxyguanosine scaffold, a versatile motif, with some truly unique characteristics. Despite being a relatively new scaffold, applications in smart materials and in drug delivery have been reported, with more yet to come.;As a contribution to the development of this work, this thesis shows a new synthetic methodology to modify the scaffold, which we expect will speed the discovery of novel properties. The aldol-type condensations here documented are a versatile strategy that has enabled the preparation of a small library of compounds. We offer full characterization of the derivatives prepared, as well as descriptions of the supramolecules formed by each derivative. Among the novel properties shown by members of this library we describe a deoxyguanosine derivative that exhibits emission enhancement upon self-assembly. This supramolecular response can be used as a fluorescence signature for self-assembly, a highly desired achievement for our systems, since it opens the door to the study of our derivatives in complex media such as the cellular environment.;Another interesting property discovered among the members of this library is the catalysis of a [2+2] photocycloaddition reaction; a rather uncommon phenomenon for supramolecular systems in solution. The supramolecule that forms after irradiation is an interesting example of social self-sorting that leads to the formation of an anisotropic discrete supramolecule.;We hope that the progress reported in this thesis will facilitate the application of deoxyguanosine-based supramolecules to the current challenges of bio- and nanotechnology, through the innovative approach of self-assembly. |
