University of Groningen
Control of translational and rotational movement at nanoscale
Stacko, Peter
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Publication date: 2017
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Stacko, P. (2017). Control of translational and rotational movement at nanoscale. University of Groningen.
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Control of Translational and
Rotational Movement at Nanoscale
The research described in this thesis was carried out at the Stratingh Institute for Chemistry, University of Groningen, Netherlands.
The work was financially supported by NanoNextNL of the Government of the Netherlands and 130 partners.
Printed by Ipskamp Printing BV, Enschede, The Netherlands. The cover image is used under Creative Commons CC0 license. ISBN: 978-94-034-0203-1
Control of Translational and
Rotational Movement at
Nanoscale
PhD Thesis
to obtain the degree of PhD at the
University of Groningen
on the authority of the
Rector Magnificus Prof. E. Sterken
and in accordance with
the decision by the College of Deans.
This thesis will be defended in public on
Friday 17 November 2017 at 16:15
by
Peter Štacko
born on 26 August 1987
in Bojnice, Slovak Republic
Supervisors
Prof. B. L. Feringa
Prof. W. R. Browne
Assessment Committee
Prof. N. H. Katsonis
Prof. R. C. Chiechi
Prof. R. J. M. Nolte
Table of Contents
Chapter I: Introduction: Artificial molecular motors
Introduction ... 10
Biological molecular motors ... 11
Artificial molecular motors ... 13
Photochemically driven molecular motors ... 22
Functional light-driven molecular motors and machines ... 26
Conclusions and outlook ... 34
References ... 36
Chapter II: Molecular dragsters: Towards controlled translational motion on surfaces Introduction ... 42
Design of the dragsters ... 47
Synthesis of the dragsters and intermediates ... 48
Photochemical and thermal isomerization studies in a solution ... 52
Single molecule STM experiments ... 55
Conclusions ... 56
Experimental part ... 57
General remarks ... 57
Synthesis ... 58
References ... 66
Chapter III: Fluorine substituted molecular motors with a quaternary stereogenic centre Introduction ... 70
Synthesis of the fluorinated motors ... 74
Photochemical and thermal isomerization studies in a solution ... 77
Conclusions ... 86
Experimental part ... 87
General remarks ... 87
Synthesis of the compounds ... 87
Chapter IV: Third generation molecular motors: Achiral unidirectional molecular motors
Introduction ... 100
Design and synthesis of p-xylene based motors ... 102
Photochemical and thermal isomerization studies in a solution ... 106
Synthesis of other third generation motors... 111
Third generation motors with a benzene-based core ... 111
Other third generation motors ... 114
Photochemical and thermal isomerization studies in a solution ... 116
Conclusions ... 118
Experimental part ... 119
General remarks ... 119
Synthesis of the compounds ... 120
References ... 126
Chapter V: Geared movement of a biaryl system controlled by a molecular motor Introduction ... 130
Design of the system ... 134
Results and discussion ... 138
Conclusions ... 149
Experimental part ... 149
General remarks ... 149
Synthesis of the compounds ... 150
Kinetic measurements ... 152
References ... 154
Chapter VI: Overcrowded alkene-based amphiphiles: Synthesis and Applications Introduction ... 158
Design of the amphiphiles... 161
Synthesis of the amphiphiles ... 162
Osmosis induced loading of vesicles into amphiphilic nanotubes ... 168
Chirality controlled self-assembled nanotubes ... 173
Conclusions ... 175
Experimental section ... 176
General remarks ... 176
Synthesis of the compounds ... 177
References ... 193
Chapter VII: Motors for investigation of the excited state substituted with rigid arms Introduction ... 198
Design of the molecules ... 200
Synthesis of the rigid-arm substituted motors ... 201
UV-Vis and fluorescence studies of the excited state ... 204
UV-Vis studies of the thermal helix inversion ... 207
Conclusions ... 208
Experimental part ... 209
General remarks ... 209
Synthesis of the compounds ... 210
References ... 218
English Summary ... 221
Nederlandse Samenvatting ... 226
Acknowledgement ... 231
