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Towards a Hydrogen Bond Mediated Directional Walker and Light Driven Molecular Shuttles

Nalbantoglu, Tugrul

[Thesis]. Manchester, UK: The University of Manchester; 2017.

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Abstract

This thesis reports the efforts towards the design and synthesis of a small moleculewalker that would potentially move along the track directionally by exploiting thesecondary interactions between the track and the walker. This thesis also reports thesynthesis 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 inspirationtowards the synthetic walkers, characteristics of a walker, previously describedsmall molecule walkers and recent progress on the synthesis of molecular shuttlesthat operate under variety of different stimuli.Chapter Two describes the design and synthetic efforts towards a molecular walkerthat has the potential to operate directionally along the track by exploiting secondaryinteractions between the walker and the track namely the hydrogen bondinginteractions introduced by subtle incorporation of excellent hydrogen bonddonor/acceptor squaramides. This chapter briefly mentions the hydrogen bondingcapabilities of squaramides on which the directional operation relies. Optimizationof critical reactions and attempted strategies for the assembly of the whole machineis 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 asa light driven molecular shuttle presents remarkable positional fidelity with highefficacy. The bistable acyl pyridyl station is incorporated as a photo active stationupon which light irradiation alters the binding affinities towards the macrocycle.Series of rotaxanes featuring different amide based stations were synthesized todetermine the best non-photo active station.