Phthalocyanine and Subphthalocyanine hybrid macrocycles: improved accessibility and synthetic control via new intermediates

Gretton, Jacob (2022) Phthalocyanine and Subphthalocyanine hybrid macrocycles: improved accessibility and synthetic control via new intermediates. Doctoral thesis, University of East Anglia.

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Abstract

This thesis is concerned with the development of synthetic pathways towards tetrabenzoporphyrin/phthalocyanine hybrid macrocycles, specifically TBTAPs and SubTBDAPs. Initial investigations further explored the latest synthetic procedures developed by the Cammidge group, which revealed the formation of unexpected products during previous work. Further development of these procedures utilizing a variety of control mechanisms successfully facilitated more selective and higher yielding procedures for ABBA and ABBB TBTAP derivatives, as well as novel ABA SubTBDAP systems. This work revealed new mechanistic insights into both macrocyclization pathways.
New intermediates were identified by this work, which were key to understanding TBTAP macrocyclization at a mechanistic level. Synthetic pathways were developed to facilitate access to a variety of new intermediates, which can be considered to be partially pre-assembled macrocycles. This methodology offers an exciting basis for future work, and may be developed to facilitate the controlled and step-wise assembly of hybrid macrocycles.
Finally, the newly developed species facilitated the development of new TBTAP and SubTBDAP synthetic routes to produce novel macrocycles. These novel precursors and pathways possess numerous advantages; TBTAPs and Sub-TBDAPs were obtained in much greater yields than previously possible, new substitution pattens can now be selectively obtained, and macrocyclization occurs with milder conditions, potentially allowing synthetic access to TBTAPs and SubTBDAPs bearing thermally sensitive functional groups.

Item Type:	Thesis (Doctoral)
Faculty \ School:	Faculty of Science > School of Chemistry
Depositing User:	Nicola Veasy
Date Deposited:	25 Oct 2023 10:42
Last Modified:	25 Oct 2023 10:42
URI:	https://ueaeprints.uea.ac.uk/id/eprint/93468
DOI:

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