Event Title
The Synthesis of Triple-Helicene and Semi-Fullerene Using Flash Vacuum Pyrolysis Techniques
Location
Diamond 145
Start Date
1-5-2014 1:00 PM
End Date
1-5-2014 2:30 PM
Project Type
Presentation
Description
This work describes our approach to the synthesis of triple-helicene and semi-fullerene using flash vacuum pyrolysis (FVP) techniques. The precursor is designed to generate a tri-acetylene that can rearrange to tri-vinylidene under high temperature FVP, which then participates in intramolecular cyclization to give triple-helicene . Based on known reactions, the semi-fullerene is anticipated to be a secondary product from triple-helicene. Preparation of precursor began with a triple Suzuki-Miyaura reaction converting 1,3,5-tri-bromobenzne into ketone-derivative. The second step of the reaction was performed by reacting the ketone-derivative with phosphorus pentachloride to make 2,2\-bis(1-chlorovinyl)-5-(2-(1-chlorovinyl)phenyl)-1,1:3,1\-terphenyl. We are now subjecting 2,2\-bis(1-chlorovinyl)-5-(2-(1-chlorovinyl)phenyl)-1,1:3,1\-terphenyl to FVP experiments to coax intramolecular cyclization to give triple-helicene, and possibly semi-fullerene. Structures for the ketone -derivative and 2,2\-bis(1-chlorovinyl)-5-(2-(1-chlorovinyl)phenyl)-1,1:3,1\-terphenyl were confirmed using NMR spectroscopy and X-ray crystallography. Molecular modeling of these products will be performed using the Gaussian program for comparison with experimentally obtained data.
Faculty Sponsor
Julie Millard
Sponsoring Department
Colby College. Chemistry Dept.
CLAS Field of Study
Natural Sciences
Event Website
http://www.colby.edu/clas
ID
377
The Synthesis of Triple-Helicene and Semi-Fullerene Using Flash Vacuum Pyrolysis Techniques
Diamond 145
This work describes our approach to the synthesis of triple-helicene and semi-fullerene using flash vacuum pyrolysis (FVP) techniques. The precursor is designed to generate a tri-acetylene that can rearrange to tri-vinylidene under high temperature FVP, which then participates in intramolecular cyclization to give triple-helicene . Based on known reactions, the semi-fullerene is anticipated to be a secondary product from triple-helicene. Preparation of precursor began with a triple Suzuki-Miyaura reaction converting 1,3,5-tri-bromobenzne into ketone-derivative. The second step of the reaction was performed by reacting the ketone-derivative with phosphorus pentachloride to make 2,2\-bis(1-chlorovinyl)-5-(2-(1-chlorovinyl)phenyl)-1,1:3,1\-terphenyl. We are now subjecting 2,2\-bis(1-chlorovinyl)-5-(2-(1-chlorovinyl)phenyl)-1,1:3,1\-terphenyl to FVP experiments to coax intramolecular cyclization to give triple-helicene, and possibly semi-fullerene. Structures for the ketone -derivative and 2,2\-bis(1-chlorovinyl)-5-(2-(1-chlorovinyl)phenyl)-1,1:3,1\-terphenyl were confirmed using NMR spectroscopy and X-ray crystallography. Molecular modeling of these products will be performed using the Gaussian program for comparison with experimentally obtained data.
https://digitalcommons.colby.edu/clas/2014/program/5