Presentation Title
progress towards the synthesis of methylene bridged interdigitated capsule
Faculty Mentor
Dr. Linda Tunstad-Gutierrez
Start Date
17-11-2018 12:30 PM
End Date
17-11-2018 2:30 PM
Location
CREVELING 93
Session
POSTER 2
Type of Presentation
Poster
Subject Area
physical_mathematical_sciences
Abstract
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.
Summary of research results to be presented
The first three compounds in the synthetic scheme were successfully produced in respectable yields. resorcin [4] arene and diquinoxaline spanned cavitand were synthesized in lower yields than expected, future endeavors will improve upon this. Tetraquinoxaline spanned cavitand was synthesized in adequate yields. NMR spectras indicate good purity of compounds.
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.