University of Groningen
Molecular motors: new designs and applications
Roke, Gerrit Dirk
IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below.
Document Version
Publisher's PDF, also known as Version of record
Publication date: 2018
Link to publication in University of Groningen/UMCG research database
Citation for published version (APA):
Roke, G. D. (2018). Molecular motors: new designs and applications. Rijksuniversiteit Groningen.
Copyright
Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons).
Take-down policy
If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim.
Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum.
The work in this thesis was performed at the Stratingh Institute for Chemistry , University of Groningen, The Netherlands.
This work was financially supported by the Ministry of Education, Culture and Science (Gravitation program 024.001.035).
Printing : Ipskamp Printing, Enschede, The Netherlands ISBN: 978-94-034-1247-4 (printed version)
Molecular Motors: New Designs and
Applications
Proefschrift
ter verkrijging van de graad van doctor aan de Rijksuniversiteit Groningen
op gezag van de
rector mangificus prof. dr. E. Sterken en volgens besluit van het College voor Promoties.
De openbare verdediging zal plaatsvinden op vrijdag 14 december 2018 om 11.00 uur
door
Promotores Prof. dr. B.L. Feringa Prof. dr. W.R. Browne Beoordelingscommissie Prof. dr. T. Bach Prof. dr. S. Otto Prof. dr. E. Otten
Table of Contents
Table of Contents
5
Chapter 1 Molecular rotary motors: Unidirectional motion
around double bonds
9
1.1 Introduction 10
1.2 Motors based on overcrowded alkenes 11
1.2.1 Rotational speed adjustment 14
1.2.2 Shifting the excitation wavelength 18
1.2.3 Improvement of the photochemical efficiency 19
1.2.4 Redox-driven motors 20
1.3 Alternative motor designs 20
1.4 Outlook 23
1.5 Outline of this thesis 24
1.6 References 25
Chapter 2 A visible light driven molecular motor based on
pyrene
31
2.1 Introduction 32
2.2 DFT calculations 33
2.3 Synthesis 34
2.4 UV/vis and 1H-NMR studies 35
Chapter 3 Tunable visible light driven molecular motors
based on oxindole
47
3.1 Introduction 48 3.2 DFT calculations 49 3.3 Synthesis 52 3.4 1H-NMR studies 523.5 UV/vis and CD studies 54
3.6 Conclusions 59
3.7 Experimental procedures 60
3.8 References 64
Chapter 4 Light-Gated Rotation in a Molecular Motor
Functionalized with a Dithienylethene Switch
67
4.1 Introduction 68
4.2 Synthesis 70
4.3 1H-NMR and UV/vis studies 71
4.4 Conclusions 75
4.5 Experimental procedures 76
4.6 References 80
Chapter 5 Photoresponsive supramolecular coordination
cage based on overcrowded alkenes
85
5.1 Introduction 86
5.2 Ligand synthesis and characterization 87
5.3 Cage formation and characterization 90
5.4 Photochemical isomerizations 97
5.5 Conclusions 98
5.6 Experimental procedures 98
Chapter 6 First generation molecular motors in polymers:
Towards photoswitchable foldamers
105
6.1 Introduction 106
6.2 Synthesis of linkers and model compounds 107
6.3 Switching studies of model compounds 109
6.4 Polymer formation and characterization 113
6.5 Conclusions 115 6.6 Experimental procedures 115 6.7 References 119
Chapter 7 Summary
123
7.1 English Summary 124 7.2 Nederlandse samenvatting 126Chapter 8 Popular science summary
129
8.1 English summary 130
8.2 Nederlandse samenvatting 131
