Synthesis and Investigation of the Naphthalene Bis-Urea Macrocycle

School Name

Governor's School for Science & Mathematics

Grade Level

12th Grade

Presentation Topic

Chemistry

Presentation Type

Mentored

Mentor

Mentor: Linda Shimizu, University of South Carolina

Oral Presentation Award

2nd Place

Abstract

Bis-Urea macrocycles can be very useful when running reactions to yield certain products. As the functionality of these macrocycles can change along with the C-shaped spacer that is used to create the macrocycle, it is desirable to investigate these different possible spacers to determine if the macrocycle they make up will be of any use. The spacer chosen to be investigated in this research is naphthalene, due to its interesting properties and its availability. The naphthalene macrocycle was synthesized, and various tests and calculations were performed on it to test how it would form, how its absorption spectrum would change, and how large its channel would be. These tests were run successfully using the protected NMC that was formed, providing insight into several of NMC’s properties. The tests show that a normal, columnar assembly would be expected from NMC, with a minimum energy value of -1374.705 Hartree. It is also seen that the absorption spectra of protected NMC and naphthalene have peaks at similar locations, 225 and 275 nm. Lastly, the tests show that the channel of NMC has a width of 0.5101 nm and a length of 0.3630 nm when measured from the centers of the atoms, meaning that there is not sufficient room for any gas to be loaded into the interior of the NMC’s channel. The research conducted helped to understand some properties of the protected NMC and make assumptions of how NMC would act once it was formed.

Location

Wall 226

Start Date

3-25-2017 10:45 AM

Presentation Format

Oral and Written

Group Project

No

COinS
 
Mar 25th, 10:45 AM

Synthesis and Investigation of the Naphthalene Bis-Urea Macrocycle

Wall 226

Bis-Urea macrocycles can be very useful when running reactions to yield certain products. As the functionality of these macrocycles can change along with the C-shaped spacer that is used to create the macrocycle, it is desirable to investigate these different possible spacers to determine if the macrocycle they make up will be of any use. The spacer chosen to be investigated in this research is naphthalene, due to its interesting properties and its availability. The naphthalene macrocycle was synthesized, and various tests and calculations were performed on it to test how it would form, how its absorption spectrum would change, and how large its channel would be. These tests were run successfully using the protected NMC that was formed, providing insight into several of NMC’s properties. The tests show that a normal, columnar assembly would be expected from NMC, with a minimum energy value of -1374.705 Hartree. It is also seen that the absorption spectra of protected NMC and naphthalene have peaks at similar locations, 225 and 275 nm. Lastly, the tests show that the channel of NMC has a width of 0.5101 nm and a length of 0.3630 nm when measured from the centers of the atoms, meaning that there is not sufficient room for any gas to be loaded into the interior of the NMC’s channel. The research conducted helped to understand some properties of the protected NMC and make assumptions of how NMC would act once it was formed.