This thesis reports the efforts towards the design and synthesis of a small molecule walker that would potentially move along the track directionally by exploiting the secondary interactions between the track and the walker. This thesis also reports the synthesis and operation of a light driven molecular shuttle featuring a novel acylpyridyl hydrazone station. Chapter One describes the biological walkers which are the source of inspiration towards the synthetic walkers, characteristics of a walker, previously described small molecule walkers and recent progress on the synthesis of molecular shuttles that operate under variety of different stimuli. Chapter Two describes the design and synthetic efforts towards a molecular walker that has the potential to operate directionally along the track by exploiting secondary interactions between the walker and the track namely the hydrogen bonding interactions introduced by subtle incorporation of excellent hydrogen bond donor/acceptor squaramides. This chapter briefly mentions the hydrogen bonding capabilities of squaramides on which the directional operation relies. Optimization of critical reactions and attempted strategies for the assembly of the whole machine is described as well. Chapter Three describes the synthesis and operation of 1- and 2- station [2]-rotaxanes that operate under light irradiation. 2- station [2]-rotaxane that function as a light driven molecular shuttle presents remarkable positional fidelity with high efficacy. The bistable acyl pyridyl station is incorporated as a photo active station upon which light irradiation alters the binding affinities towards the macrocycle. Series of rotaxanes featuring different amide based stations were synthesized to determine the best non-photo active station.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:740310 |
| Date | January 2017 |
| Creators | Nalbantoglu, Tugrul |
| Contributors | Leigh, David ; Greaney, Michael |
| Publisher | University of Manchester |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | https://www.research.manchester.ac.uk/portal/en/theses/towards-a-hydrogen-bond-mediated-directional-walker-and-light-driven-molecular-shuttles(fb210b38-4079-4376-942e-b907a8f82d3f).html |
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