progress towards the synthesis of methylene bridged interdigitated capsule

CREVELING 93

Resorcin [4] arene cavitands and their derived heterocapsules are of great interest in the field of host-guest chemistry due to the ease with which they are able to be functionalized and alternate between enclosed capsules and open conformers .The primary objective of this research is to synthesize a heterodimer “interdigitated” capsule 1 that is more rigid than the previous generation of capsules designed by the Tunstad group. The proposed capsule will be composed of two functionalized resorcin[4]arene macrocycles, each with differing number of methylene and quinoxaline linkers. It is our hypothesis that the incorporation of methylene groups into the bottom half of the capsule will induce conformational rigidity that will allow for host guest binding interactions. The work that has been completed thus far includes the synthesis of the first three intermediates and their corresponding characterizations via ¹H-NMR (Nuclear Magnetic Resonance). Upon successful synthesis of the desired capsule, physical conformational studies will be carried out via ¹H NMR, variable temperature NMR, ¹³C NMR, and mass spectrometry in order to determine extent of capsule conformational.