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Eindhoven University of Technology MASTER Towards Non-Covalent Eindhoven University of Technology MASTER Towards non-covalent synthesis a study on formamidines van der Woude, P.H. Award date: 2020 Link to publication Disclaimer This document contains a student thesis (bachelor's or master's), as authored by a student at Eindhoven University of Technology. Student theses are made available in the TU/e repository upon obtaining the required degree. The grade received is not published on the document as presented in the repository. The required complexity or quality of research of student theses may vary by program, and the required minimum study period may vary in duration. General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. • Users may download and print one copy of any publication from the public portal for the purpose of private study or research. • You may not further distribute the material or use it for any profit-making activity or commercial gain Towards Non-Covalent Synthesis: A Study on Formamidines Graduation report of Pieternella Hendrika van der Woude Supervisor: dr. G. Vantomme Supervising professor: prof. dr. E.W. Meijer Advising committee: prof. dr. ir. A.R.A. Palmans dr. L.K.E.A. Abdelmohsen Eindhoven, October 2019 Laboratory of Macromolecular and Organic Chemistry Faculty of Chemical Engineering and Chemistry Eindhoven University of Technology Summary ‘I think, therefor I am’ – René Descartes, 1637 Thinking, the most essential form of being, witnessed by Descartes, is a process of molecules. It is however a process of such high complexity that chemists are still far away of mimicking it. But at the same time, complexity is the way chemists are going. History has shown a shift from molecules to aggregates, and now is the time to synthesize complex structures. However, self-assembly might not suffice for the creation of complex structures, and another approach is needed. This new approach is embodied by non-covalent synthesis: combining covalent and non-covalent synthesis steps with the aim to create dynamic, complex structures. This research aims to obtain more insight in non-covalent synthesis. However, non-covalent synthesis is a broad concept and therefor the subject of this study is narrowed down to the detailed investigation of formamidines. Formamidines belong to an interesting class of dynamic molecules which can exhibit strong non-covalent interactions with carboxylic acids and perform dynamic covalent chemistry in the form of amine exchange. First, the synthesis and purification of both aromatic and aliphatic symmetrical disubstituted formamidines was studied, which resulted in successfully obtaining pure N,N’-disubstituted formamidines with phenyl, octyl, dodecyl and p-methoxyphenyl side groups. The interactions of these formamidines were studied using different NMR techniques. The interaction between formamidines and carboxylic acids could be demonstrated by NOESY, and the interaction strength could be quantified by 1H NMR. Lastly the ability of formamidines to exchange amines was studied by 1H NMR. Both aliphatic and aromatic formamidines were found to be able to exchange their amines. For aliphatic formamidines, exchange was only observed in the presence of one equivalent benzoic acid, whereas for aromatic formamidines exchange was observed both in presence and absence of a carboxylic acid. Conclusively, the distinct dynamic properties of formamidines have been studied in order to gain a complete and detailed understanding of this building block. The gained insights can be applied to use formamidines in non-covalent synthesis. Table of Contents Chapter 1. Exploring formamidines: Towards non-covalent synthesis 1.1 Towards non-covalent synthesis ...................................................................................................................... 1 1.2 Challenges on the road towards non-covalent synthesis .................................................................................. 2 1.3 The first non-covalent synthetic steps .............................................................................................................. 3 1.4 The aim and outline of this thesis: a strategy towards non-covalent synthesis ................................................ 6 References .............................................................................................................................................................. 7 Chapter 2. Synthesis of symmetrical disubstituted formamidines 2.1 Introduction .................................................................................................................................................... 13 2.2 Synthesis of formamidines ............................................................................................................................. 14 2.3 Purification of formamidines.......................................................................................................................... 16 2.4 Discussion and conclusion ............................................................................................................................. 17 2.5 Experimental section ...................................................................................................................................... 17 References ............................................................................................................................................................ 20 Chapter 3. Non-covalent interactions with formamidines 3.1 Introduction .................................................................................................................................................... 23 3.2 Characterization of synthesized formamidines............................................................................................... 24 3.3 Dimerization ................................................................................................................................................... 24 3.4 Interaction strength ......................................................................................................................................... 26 3.5 Conclusion and outlook .................................................................................................................................. 29 3.6 Experimental section ...................................................................................................................................... 29 References ............................................................................................................................................................ 30 Chapter 4. Amine exchange in formamidines 4.1 Introduction .................................................................................................................................................... 33 4.2 Amine exchange experiments ........................................................................................................................ 35 4.3 Conclusion ..................................................................................................................................................... 41 4.4 Experimental section ...................................................................................................................................... 42 References ............................................................................................................................................................ 43 Conclusions and outlook .................................................................................................................................... 45 Acknowledgement .............................................................................................................................................. 49 Appendix ............................................................................................................................................................. 51 Chapter 1. Exploring formamidines: Towards non-covalent synthesis ‘Chemists make and study molecules.’ – G.M. Whitesides et al., 1995 1.1 Towards non-covalent synthesis Already in 1995, Whitesides et al. wrote that chemists are known for making and studying molecules. However, he envisioned that making and studying aggregates would become more important.1 The motivation is that new properties emerge from ensembles of molecules, giving more properties than the sum of the individual parts. And history has not proved Whitesides wrong. Instead, making complex and lifelike molecular systems and materials is even more complicated than, and builds further on the study on aggregates.2 The ambition to make molecules and molecular systems with increasing complexity originates from what we see in Nature. First, there was the desire to make molecules of increasing complexity, which resulted in the synthesis of amongst others (the classical example) vitamin B12. And by now, organic chemists are capable of making almost any molecules with the right resources.3 Secondly, as stated by Whitesides et al., there was the desire to make aggregates of molecules, known as supramolecular chemistry. Our knowledge and understanding about supramolecular chemistry is still growing at a high Figure 1: Plea for a paradigm shift towards multi-step non-covalent synthesis.
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