1.1 Porphyrins - Friedrich-Alexander-Universität Erlangen-Nürnberg

Table of Contents
1 Introduction 1
1.1 Porphyrins – A General Survey 4
1.2 Photodynamic Therapy (PDT) 14
2 State of the Art & Aims 21
2.1 State of the Art 21
2.2 Aim of the Work 24
3 Discussion and Results 25
3.1 Semi-Natural Cycloketo-Porphyrins 25
3.2 Synthetic Cycloketo-Porphyrin Systems 31
3.2.1 o-(Bromomethyl) Substituted Porphyrin Building Blocks Revisited 31
3.2.2 Setup of a Synthetic Pathway to Novel Cycloketo-Porphyrins 34
3.2.3 Mono-Exocyclic Cycloketo-Porphyrin 53 - Characterization Data and
Photophysical & Electrochemical Investigations 43
3.2.4 Chemical Reactivity of Mono-Exocyclic Cycloketo-Porphyrin 53 61
3.2.5 Inherent Chirality and Resolution of Cycloketo-Porphyrin 53 70
3.2.6 Studying the Structure-Properties-Relations 75
3.2.7 Approaching Polyexocyclic Cycloketo-Porphyrin Systems 92
3.2.8 Cycloketo-Porphyrin Systems with Additional Functionality 109
3.2.9 Potential Strategies for the Development of Novel Photosensitizers 124
4 Summary 131
5 Zusammenfassung 134
6 Experimental Section 137
6.1 Chemicals, Methods and Equipment 137
6.2 Studied Compounds – Syntheses & Characterization 140
6.2.1 Preliminaries 140
6.2.2 Semi-Natural Cycloketo-Porphyrin Systems 141
6.2.3 General Procedures (GPs) 143
6.2.4 AB3-Type Mono-Exocyclic Cycloketo-Porphyrins and Their Precursors 146
6.2.5 A2B2-Type Poly-Annulated Cycloketo-Porphyrin Systems and Precursors 162
6.2.6 AB2C-Type Mono-Exocyclic Cycloketo-Porphyrins, Precursors &
Derivatives 178
7 References 189
Appendix 197
Publications, Acknowledgements (Danksagung), Curriculum Vitae