Biocompatible Photochromic Diketopiperazine-based Supramolecular Hydrogelator Systems
Anna-Lena Leistner
Cite this publication as
Anna-Lena Leistner, Biocompatible Photochromic Diketopiperazine-based Supramolecular Hydrogelator Systems (2023), Logos Verlag, Berlin, ISBN: 9783832583248
Description / Abstract
In the course of the last twenty years, the research interest in 'photochemical switches' highly increased. They react on light, which can be controlled with excellent spatiotemporal precision, yet it is orthogonal towards most elements of chemical and biochemical systems. Therefore, light is an attractive trigger to control or study biological function or functional materials. In this work, the excellent properties of azobenzene photoswitches were combined with the cyclic dipeptide structural motif, resulting in phototriggered supramolecular low-molecular-weight gelators (LMWGs). Hydrogels are soft materials, which often find application in biomedical context and can be formed by self-assembly of LMWGs. They classify by their self-healing properties, thixotropy, on-demand reversibility and stimuli responsiveness, for example to light. The photoswitches inside photochromic hydrogels react in spatiotemporal precision to light irradiation and are excellent candidates for photo-controlled drug release. The versatility of azobenzene containing DKP-Lys hydrogelators was demonstrated in this thesis.
Table of content
- BEGINN
- Kurzzusammenfassung / Abstract in German
- Abstract
- 1 Introduction
- 1.1 Molecular photoswitches
- 1.2 Gels
- 1.3 Aggregation induced emission
- 2 Objective
- 3 Results and discussion
- 3.1 Fluorinated azobenzenes switchable with red light
- 3.2 Symmetrical chiral TFAB gelator
- 3.3 Symmetrical chiral gelator ‒ model system for the addition of dopants
- 3.4 Transfer of the composite alginate system to PAP-DKP-Lys
- 3.5 Transfer of the composite alginate system to F2-PAP-DKP-Lys
- 3.6 A new red light triggered LMWG ‒ Cl4-PAP-DKP-Lys
- 3.7 A new red light triggered LMWG – Cl2-F2-PAP-DKP-Lys
- 3.8 New AIE-gen – Naphthalimide-(F2)-PAP-DKP-Lys conjugate
- 4 Summary and Outlook
- 4.1 Fluorinated azobenzenes switchable with red light
- 4.2 Symmetrical chiral TFAB gelator
- 4.3 Symmetrical chiral gelator ‒ model system for the addition of dopants
- 4.4 Transfer of the composite alginate system to (F2)-PAP-DKP-Lys
- 4.5 New red light triggered LMWG ‒ Cl4/Cl2-F2-PAP-DKP-Lys
- 4.6 New AIE-gens - Solvent dependent aggregation
- 5 Experimental part
- 5.1 General remarks
- 5.2 Analytics and devices
- 5.3 Fluorinated azobenzenes switchable with red light
- 5.4 Symmetric chiral TFAB gelator
- 5.5 Symmetrical chiral gelator ‒ model system for the addition of dopants
- 5.6 Transfer of the composite alginate system to PAP-DKP-Lys
- 5.7 Transfer of the composite alginate system to F2-PAP-DKP-Lys
- 5.8 A new red light triggered LMWG ‒ Cl4-PAP-DKP-Lys
- 5.9 A new red light triggered LMWG ‒ CL2-F2-PAP-DKP-Lys
- 5.10 New AIE-gen – Naphthalimide-(F2)-PAP-DKP-Lys conjugate
- 6 List of Abbreviations
- 7 Literature index
- 8 Appendix
- 8.1 Curriculum Vitae
- 8.2 List of Publications
- 8.3 Acknowledgements