Designing Resorcinarene Cages

Chatterjee, Puranjan (2018) Designing Resorcinarene Cages. Masters thesis, Indian Institute of Science Education and Research Kolkata.

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Abstract

The present work aims to make resorcinarene cage structures by attaching them through their lower rim of phenyl group and attaching them by ethynyl spacers to make a controllable cavity which can further be modified if needed. Our aim was to introduce ethynyl spacers to connect two crown conformers of resorcinarene rings from their lower rim. If we could accomplish our aim of making such connections, then we could make very specific and non-flexible cavities as per our need which can further be used for applications in host-guest chemistry. With this idea in mind we started our journey in this path, to synthesize resorcinarene cages. As the present approach of coupling the resorcinarene ring led to some obscure results, an alternative approach was taken to synthesize precursor dialdehydes with the required attachments and make direct condensation with resorcinol to form the cage compounds. This approach would relieve us from the potential cumbersome and less plausible coupling reaction at the ring. In conclusion, though the plan of formation of resorcinarene cage is pretty simple but due to its solubility problem, it is creating a menace in the process of characterization. Hence most of our cage compound formation attempts have concluded with the formation of compounds which could not be characterized. Though it was a major setback in our scheme, to be unable to characterize our final compounds, but there were two major accomplishments as well in this project. Firstly, a successful method of selectively forming the crown conformer was devised in a relatively much less time scale. Secondly, , a new unreported resorcinarene compound was synthesized with very unique characteristic color (red). All the previously reported resorcinarene derivatives are pale yellow, pale orange or white in color. But this crimson red colored compound surely needs some attention and further investigation. The major hurdle of this path to be counteracted is the solubility of the plausible cage compounds. Therefore, if some solubilizing group is incorporated in the resorcinarene scaffold, then the further formed products might have better solubility to give us an insight on what is exactly happening in the reaction medium.

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