Water Soluble Rotaxane

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2008

A PROTEIN-APPENDED ROTAXANE
BY

HAYTHIM HASSANEIN
SUPERVISOR PALL THORDARSON

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Contents

Certificate of Orignality .............................................................................................................. i Abstract ...................................................................................................................................... ii Acknowledgements ................................................................................................................... iii Table of Contents ....................................................................................................................... 2 1. Introduction ............................................................................................................................ 5 2. Natural Protein-Appended Rotaxanes.................................................................................... 6 3. Bioconjugate Chemistry and Rotaxanes ................................................................................ 8 4. Earliest Rotaxane Synthesis ................................................................................................... 9 5. Rotaxanes & Nanodevices ................................................................................................... 10 5.1 Molecular Motors................................................................................................... 10 5.2 Molecular Shuttles ................................................................................................. 12 5.3 Molecular Muscles ................................................................................................. 14 5.4 Molecular Electronics ............................................................................................ 16 6. Approach and Synthesis ....................................................................................................... 17 6.1 Pre-assembly in Non-Aqueous Solvents ............................................................... 17 6.2 Axial Component Motifs ...................................................................................... 17 6.3 Macrocycle Component Motifs ............................................................................ 18 6.4 Stopper Component Motifs ................................................................................... 20 6.5 Approaches ........................................................................................................... 20 6.6 Characterisaiton .................................................................................................... 26 7. Applications ......................................................................................................................... 27 7.1 Drug Delivery ........................................................................................................ 27 7.2 Biosensor Applications .......................................................................................... 28 8. Experimental ........................................................................................................................ 30 8.1 Azo-based Reactions ........................................................................................ 30 8.1.1 8.1.2 Synthesis of 4,4-Azodiphenol (1)........................................................ 30 Synthesis of 4-Bromobutoxy Nitrobenzene (2) .................................. 31

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8.1.3 8.1.4

Synthesis of trans-Bis-(E)-((Bromobutoxy)phenyl)diazene) (3) ........ 31 Synthesis of trans-4,4'-Bis((6-hydroxyhexoxy)azobenzene) (4) ......... 32

8.1.5 Attempted Synthesis of trans-4,4‟-Bis((6maleimidohexoxy)azobenzne) (5) ................................................................... 32 8.2 Viologen-Based Reactions ............................................................................... 33 8.2.1 Synthesis of 4,4‟-Bipyridinium-N,N-di(propylammonia) hexaflurophosphate...
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