University of Groningen
Photoresponsive supramolecular soft materials in aqueous media
Chen, Shaoyu
DOI:
10.33612/diss.107818650
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Publication date: 2019
Link to publication in University of Groningen/UMCG research database
Citation for published version (APA):
Chen, S. (2019). Photoresponsive supramolecular soft materials in aqueous media. Rijksuniversiteit Groningen. https://doi.org/10.33612/diss.107818650
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Photoresponsive
Supramolecular Soft Materials
in Aqueous Media
The work described in this thesis was carried out at the Stratingh Institute for
Chemistry, University of Groningen, The Netherlands, and at the School of
Textiles and Clothing, Jiangnan University, China.
This work was financially supported by the Netherlands Organization for
Scientific Research (NWO-CW, NWO-Top Grant, ERC), the China
Scholarship Council, National Natural Science Foundation of China, the
Excellent Doctoral Cultivation Project of Jiangnan University
Cover, bookmark and illustrations: designed and drawn by Qian Wang
Printed by Ipskamp Drukkers BV, Enschede, The Netherlands
ISBN: 978-94-034-2011-0 (Printed Version)
ISBN: 978-94-034-2010-3 (Electronic Version)
Photoresponsive Supramolecular
Soft Materials in Aqueous Media
PhD thesis
to obtain the degree of PhD at the University of Groningen
On the authority of the
Rector Magnificus prof. C. Wijmenga and in accordance with the decision by the College of Deans. This thesis will be defended in public on Friday 13 December 2019 at 09.00 hour
by
Shaoyu Chen
born on 06 June 1990 in Guangdong, China
Supervisors
Prof. B. L. Feringa Prof. C. WangCo-supervisor
Dr. S. J. WezenbergAssessment committee
Prof. E. J. R. Sudhölter Prof. P. Rudolf Prof. W.R. Browne Prof. P. MaPhotoresponsive Supramolecular
Soft Materials in Aqueous Media
Proefschrift
ter verkrijging van de graad van doctor aan de Rijksuniversiteit Groningen
op gezag van de
rector mangificus prof. dr. C. Wijmenga en volgens besluit van het College voor Promoties.
De openbare verdediging zal plaatsvinden op vrijdag 13 december 2019 om 09.00 uur
door
Shaoyu Chen
geboren op 06 juni 1990 te Guangdong, China
Promotores
Prof. dr. B. L. Feringa Prof. dr. C. WangCopromotor
Dr. S. J. WezenbergBeoordelingscommissie
Prof. dr. E. J. R. Sudhölter Prof. dr. P. Rudolf Prof. dr. W.R. Browne Prof. dr. P. Mai
Table of Content
Chapter 1
Supramolecular Self-Assembly of Photoresponsive Molecular Amphiphiles in
Aqueous Media ... 1
1.1 Introduction ... 3
1.2 Photoresponsive molecular amphiphiles ... 4
1.3 Dynamic functions of photoresponsive molecular amphiphiles at air-water interfaces ... 5
1.4 Functional supramolecular self-assembly of photoresponsive molecular amphiphiles in solutions ... 13
1.4.1 Isotropic self-assembly of photoresponsive molecular amphiphiles ... 14
1.4.2 Anisotropic self-assembly of photoresponsive molecular amphiphiles ... 25
1.5 Summary and outlook ... 31
1.6 Outline of this thesis ... 32
1.7 References ... 34
Chapter 2 Amphiphilic Azobenzene Doped Photoresponsive Foams ... 43
2.1 Introduction ... 45
2.2 Results and Discussion ... 46
2.2.1 Molecular design and synthesis ... 46
2.2.2 Isomerization analysis of NAACn ... 47
2.2.3 Photoresponsive foams of NAACn doped in SDS foaming system ... 51
2.3 Conclusions ... 55
2.4 Acknowledgments ... 55
2.5 Experimental Data ... 55
2.6 References ... 57
Chapter 3 Amphiphilic Nonionic Azobenzene Doped Photoresponsive Foams for a Recycled Pigment Coloring Approach ... 63
3.1 Introduction ... 65
3.2 Results and Discussion ... 67
3.2.1 Molecular design and synthesis ... 67
3.2.2 Photoisomerization of NAAPEG ... 68
3.2.3 Photoresponsive foams of NAAPEG ... 70
3.2.4 Fabric properties colored with different concentrations of pigment dispersion ... 73
Cotton fabric properties colored with the recycled foam coloring process 3.2.5 Polyester fabric properties colored with the recycled pigment foam coloring
process ... 77 3.3 Conclusions ... 78 3.4 Acknowledgments ... 79 3.5 Experimental Data ... 79 3.6 References ... 81 Chapter 4 Photoresponsive Foams from a Cationic Azobenzene Amphiphile (CAAC4) for a Recycled Coloring Approach ... 87
4.1 Introduction ... 89
4.2 Results and Discussion ... 91
4.2.1 Molecular design and synthesis ... 91
4.2.2 Photoisomerization of CAAC4 ... 91
4.2.3 Thermal stability of CAAC4 ... 93
4.2.4 Foam properties of CAAC4 ... 95
4.2.5 Effects of CWPU dye on foam properties of CAAC4... 97
4.2.6 Cotton fabric properties colored with different concentrations of CWPU dye ... 98 4.2.7 ... 101 4.3 Conclusions ... 103 4.4 Acknowledgments ... 104 4.5 Experimental Data ... 103 4.6 References ... 106 Chapter 5 Fast Photoresponsive Foams from a Cationic Azobenzene Amphiphile (CAAC8) ... 111
5.1 Introduction ... 113
5.2 Results and Discussion ... 114
5.2.1 Molecular design and synthesis ... 114
5.2.2 Photoisomerization of CAAC8 ... 115
5.2.3 Surface activity of CAAC8 ... 117
5.2.4 Fast photoresponsive foams ... 119
5.3 Conclusions ... 122
iii Chapter 6
Supramolecular Assembly Transformations of a Molecular Motor Amphiphile
Controls Macroscopic Foam Properties ... 131
6.1 Introduction ... 133
6.2 Results and Discussion ... 135
6.2.1 Molecular design and synthesis ... 135
6.2.2 Photoisomerization and thermal helix inversion steps to control packing parameters of MA ... 136
6.2.3 Supramolecular assembly transformation at microscopic length-scales... 140
6.2.4 Macroscopic photoresponsive foam ... 143
6.3 Conclusions ... 148
6.4 Acknowledgments ... 148
6.5 Experimental Data ... 149
6.6 References ... 153
Chapter 7 Biocompatible Macroscopic Strings of Motor Amphiphiles for Cell Growth161 7.1 Introduction ... 163
7.2 Results and Discussion ... 164
7.2.1 Molecular design and synthesis ... 164
7.2.2 Photoisomerization of motor amphiphiles ... 166
7.2.3 Supramolecular assembly of motor amphiphiles ... 167
7.2.4 Biocompatibility and cell growth onto the macroscopic strings ... 171
7.3 Conclusions ... 173 7.4 Acknowledgments ... 173 7.5 Experimental Data ... 174 7.6 References ... 179 Summary 187 English summary ... 188 Nederlandse samenvatting ... 191 Chinese summary ... 194 Appendix 201 Appendix-Section A ... 202 Appendix-Section B ... 204 Appendix-Acknowledgements ... 208
