The study of cavitands and carceplexes with C5 symmetry

• Main Author: Place, Samuel
• Language: English
• Published: 2009
• Online Access: http://hdl.handle.net/2429/11589

This thesis presents a study of the synthesis of carceplex 65•2 DMF. [5]cavitand 58 was synthesized and the 2-methyl groups then underwent selective free radical bromination to give Br-[5]cavitand 60, which was converted to SH-[5]cavitand 61. The coupling of two molecules SH-[5]cavitand 61 proved to be successful and led to the formation of carceplex 65•2 DMF which has a C ₅ symmetry unique to carceplexes as well as hemispheres that are linked by disulfide bonds. ¹H NMR data showed carceplex 65 to have encapsulated 2 DMF molecules. MALDI MS experiments confirmed the correct mass of disulfide carceplex 65•2 DMF. Carceplex 65•2 DMF is an intriguing system for several reasons: 1) 65•2 DMF is the first ever carceplex that possesses a C ₅ symmetry 2) 65•2 DMF is the first carceplex system that has disulfide linkers and 3) 65 has the ability to encapsulate multiple guest molecules (2 DMF's) within its interior. These unique characteristics have been investigated and shall be reported within this thesis.