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SYNTHESIS AND CONFORMATIONAL ANALYSIS OF POLYARENE DENDRIMERS

Mistry, Jinesh

[Thesis]. Manchester, UK: The University of Manchester; 2016.

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Abstract

Polyarene dendrimers with rigid aromatic regions are of interest due to their shape persistentnature.A novel series of G1 dendrimers containing a substituted 1,3-phenyl core are reportedand were found to exhibit atropisomerism. This was investigated in the solid state (X ray),in solution (NMR), and via computational studies.The synthesis of fluorinated G1 dendrimers allowed for the analysis of interconversionbetween conformations via 19F-19F EXSY NMR (exchange spectroscopy). These wereshown to exist as two distinct sets of three interconverting atropisomers. Eachatropisomer was identified as well as their respective interconversion pathway. By increasing the size of the core of the G1 dendrimers resulted in physical separationof atropisomers by preparative HPLC. Results suggest certain conformers areenergetically unfavourable reducing the total number of atropisomers observed.

Bibliographic metadata

Type of resource:
Content type:
Administered thesis
Form of thesis:
Traditional
Type of submission:
Doctoral level ETD - final
Thesis title:
SYNTHESIS AND CONFORMATIONAL ANALYSIS OF POLYARENE DENDRIMERS
Degree type:
Doctor of Philosophy
Degree programme:
PhD Chemistry
Publication date:
2016-02-25T15:50:44
Institution:
The University of Manchester
Location:
Manchester, UK
Total pages:
333
Abstract:
Polyarene dendrimers with rigid aromatic regions are of interest due to their shape persistentnature.A novel series of G1 dendrimers containing a substituted 1,3-phenyl core are reportedand were found to exhibit atropisomerism. This was investigated in the solid state (X ray),in solution (NMR), and via computational studies.The synthesis of fluorinated G1 dendrimers allowed for the analysis of interconversionbetween conformations via 19F-19F EXSY NMR (exchange spectroscopy). These wereshown to exist as two distinct sets of three interconverting atropisomers. Eachatropisomer was identified as well as their respective interconversion pathway. By increasing the size of the core of the G1 dendrimers resulted in physical separationof atropisomers by preparative HPLC. Results suggest certain conformers areenergetically unfavourable reducing the total number of atropisomers observed.
Keyword(s):
Thesis main supervisor(s):
Degree grantor:
Language:
en

Institutional metadata

University researcher(s):
Academic department(s):

Record metadata

Manchester eScholar ID:
uk-ac-man-scw:297844
Created by:
Mistry, Jinesh
Created:
25th February, 2016, 15:50:44
Last modified by:
Mistry, Jinesh
Last modified:
9th September, 2016, 13:05:23

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