SYNTHESIS AND CONFORMATIONAL ANALYSIS OF POLYARENE DENDRIMERS

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.

Date of Award	1 Aug 2016
Original language	English
Awarding Institution	The University of Manchester
Supervisor	John Gardiner (Supervisor)