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University of Groningen

Structure-Function Relationships in Dynamic Combinatorial Libraries

Altay, Meniz

DOI:

10.33612/diss.90038152

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: 2019

Link to publication in University of Groningen/UMCG research database

Citation for published version (APA):

Altay, M. (2019). Structure-Function Relationships in Dynamic Combinatorial Libraries. University of Groningen. https://doi.org/10.33612/diss.90038152

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Structure-Function Relationships in

Dynamic Combinatorial Libraries

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Cover Design: Yi˘git Altay - www.yigitaltay.com Printed by: Gildeprint - The Netherlands

ISBN: 978-94-034-1805-6 (print) ISBN: 978-94-034-1804-9 (e-book)

The work described in this thesis was carried out at the Stratingh Institute for Chem-istry, University of Groningen, the Netherlands.

This work financially supported by the European Research Council (ERC), the Netherlands Organisation for Scientific Research (NWO) and the Ministry of Educa-tion, Culture and Science (Gravity program 024.001.035).

Structure-Function Relationships in

Dynamic Combinatorial Libraries

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 6 September 2019 at 11.00 hours

by

Meniz Altay

born on 11 October 1988 in Edirne, Turkey

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Cover Design: Yi˘git Altay - www.yigitaltay.com Printed by: Gildeprint - The Netherlands

ISBN: 978-94-034-1805-6 (print) ISBN: 978-94-034-1804-9 (e-book)

The work described in this thesis was carried out at the Stratingh Institute for Chem-istry, University of Groningen, the Netherlands.

This work financially supported by the European Research Council (ERC), the Netherlands Organisation for Scientific Research (NWO) and the Ministry of Educa-tion, Culture and Science (Gravity program 024.001.035).

Structure-Function Relationships in

Dynamic Combinatorial Libraries

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 6 September 2019 at 11.00 hours

by

Meniz Altay

born on 11 October 1988 in Edirne, Turkey

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Supervisors Prof. S. Otto Prof. W. R. Browne Assessment Committee Prof. M. Pittelkow Prof. R. P. Sijbesma Prof. M. D. Witte

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Supervisors Prof. S. Otto Prof. W. R. Browne Assessment Committee Prof. M. Pittelkow Prof. R. P. Sijbesma Prof. M. D. Witte

Contents

1 Advances on Complex Molecular Systems 1

1.1 Introduction . . . 2

1.2 Structure-to-Function in Biology . . . 2

1.3 What is Life? . . . 4

1.4 Steps Towards Synthetic ‘Living’ Systems . . . 5

1.5 Systems Chemistry . . . 6

1.6 Dynamic Combinatorial Chemistry (DCC) . . . 6

1.7 Out-of-equilibrium Systems . . . 7

1.8 Self-Replication . . . 9

1.9 Diversification of Replicators and Molecular Ecosystems . . . 13

1.10 Content and Outline of This Thesis . . . 15

1.11 References . . . 17

2 The Influence of Building Block Design on the Outcome of Type and Size of Supramolecular Block Copolymers 21 2.1 Introduction . . . 22

2.2 Results and Discussion . . . 24

2.3 Conclusions . . . 45 2.4 Acknowledgements . . . 46 2.5 Experimental Section . . . 47 2.6 Appendix . . . 49 2.7 References . . . 63 v

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Contents 3 Spacer Length: A Factor for Tuning Self-Replication in Dynamic

Combinatorial Libraries 65

3.1 Introduction . . . 66

3.2 Results and Discussion . . . 67

3.3 Conclusions . . . 83

3.4 Acknowledgements . . . 83

3.5 Experimental Section . . . 84

3.6 Appendix . . . 86

3.7 References . . . 117

4 Parasitic Behavior of Self-Replicating Molecules 119 4.1 Introduction . . . 120

4.2 Results and Discussion . . . 122

4.3 Conclusion . . . 126

4.4 Acknowledgements . . . 127

4.5 Materials and Methods . . . 128

4.6 References . . . 171

5 Towards Replicator Diversification Under Far-from-Equilibrium Con-ditions 175 5.1 Introduction . . . 176

5.2 Results and Discussion . . . 178

5.3 Conclusions . . . 193

5.4 Acknowledgements . . . 194

5.5 Experimental Section . . . 194

5.6 References . . . 203

6 Conclusion and Perspectives 205 6.1 References . . . 209 Summary 211 Samenvatting 213 Acknowledgements 215 vi

Chapter 1

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