Presentation Title

Progress towards a new synthetic route for 1,6-diiodo-E,E,E-1,3,5-hexatriene

Presenter Information

Lassana DiawaraFollow

Faculty Mentor

Michael Sponsler

Start Date

17-11-2018 12:30 PM

End Date

17-11-2018 2:30 PM

Location

CREVELING 91

Session

POSTER 2

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

The goal of this experiment is to be able to design a new synthetic pathway to synthesizing 1,6-diiodo-E,E,E-1,3,5-hexatriene. By being able to synthesize 1,6-diiodo-E,E,E-1,3,5-hexatriene, it would allow us to be able to further polymerize 1,6-diiodo-E,E,E-1,3,5-hexatriene in a Urea inclusion complex to form highly ordered polyactylene. Three different synthetic pathways were taken where taken using three different catalysts. The reaction conditions were optimized for all reactions to improve the yield and order of the polyacetylene. It was found that some of our reaction conditions was able to give product that was able to be partially identified. Furthermore, the optimization of the reaction conditions allowed us to learn more about the formation of our target compound.

Summary of research results to be presented

Though we were not able to achieve our main goal of finding a more reliable way of synthesizing 1,6-diiodo-E,E,E-1,3,5-hexatriene(2), but we were able to learn a lot about the synthetic requirement. One of the first speculations as to why some of our synthetic pathways to our target did not work may be because we were modeling the reaction from literature that was based on molecules that only had one terminal alkyne. Though we were able to make some adjustments stoichiometrically, sometimes increasing the equivalence may cause the reaction to not work as suspected. So, we will need to make many more adjustments to the pathways in order to make them work. A prime example of is the PdCl2(PPh3)2catalyzed reaction, where we were able to get peaks in the alkene region but the product was not our target compound. On the other hand, even though the peaks did not correspond to our target compound we were able to characterize the compound to be 2,5-diiodo-E-hexatriene(7)and its stereoisomer 2,5-diiodo-Z-hexatriene (8), which have not yet been seen in literature. Furthermore, to improve the outcome of this reaction, I would continue to change conditions and monitor them to see how they affect the outcome.

This document is currently not available here.

Share

COinS
 
Nov 17th, 12:30 PM Nov 17th, 2:30 PM

Progress towards a new synthetic route for 1,6-diiodo-E,E,E-1,3,5-hexatriene

CREVELING 91

The goal of this experiment is to be able to design a new synthetic pathway to synthesizing 1,6-diiodo-E,E,E-1,3,5-hexatriene. By being able to synthesize 1,6-diiodo-E,E,E-1,3,5-hexatriene, it would allow us to be able to further polymerize 1,6-diiodo-E,E,E-1,3,5-hexatriene in a Urea inclusion complex to form highly ordered polyactylene. Three different synthetic pathways were taken where taken using three different catalysts. The reaction conditions were optimized for all reactions to improve the yield and order of the polyacetylene. It was found that some of our reaction conditions was able to give product that was able to be partially identified. Furthermore, the optimization of the reaction conditions allowed us to learn more about the formation of our target compound.