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II ACKNOWLEDGEMENTS III TABLE OF CONTENTS IV 1.0.0 INTRODUCTION 1 1.1.1 DENDRIMERS AS POLYMERS 1 1.1.2 DENDRIMER STRUCTURE 3 1.1.3 DISCOVERY AND INITIAL RESEARCH 4 1.1.4 SYNTHETIC METHODS 7 1.1.5 APPLICATION IN MEDICINE 9 1.2.0 BACKGROUND 12 1.2.1 CLICK CHEMISTRY 12 1.2.1A COPPER-CATALYZED AZIDE-ALKYNE CLICK CHEMISTRY 13 1.2.1B THIOL-ALKENE 14 1.2.1C THIOL-MICHAEL ADDITION CHEMISTRY 15 1.2.2 CLICK APPLIED TO DENDRIMER SYNTHESIS 16 1.2.3 ORTHOGONAL CLICK REACTIONS 17 1.2.4 DRAWBACKS OF CLICK STRATEGIES TO DATE 19 1.3.0 PROPOSAL 19 1.4.0 DISCUSSION 22 1.4.1 DISULFIDE ROUTE 22 1.4.2 PHOTOCLEAVABLE ROUTE 26 1.4.3 THIOACETATE ROUTE 27 1.4.4 DENDRIMER 30 1.5.0 EXPERIMENTAL 35 1.5.1 GENERAL METHODS 35 1.5.2 SYNTHESIS 35 1.6.0 CONCLUSION 39 1.6.1 IF THIS IS DENDRITE I DON'T WANT TO KNOW WHAT’S DENDWRONG 39 1.6.2 FUTURE WORK 39 2.0.0 INTRODUCTION TO THIOL-ENE SELECTIVE REACTIONS 44 2.1.0 DISCUSSION 44 2.1.1 THIOL-ALKENE SELECTIVITY 45

Synergy of Dynamic Covalent and Click Methodologies in Dendrimer Synthesis: A Study of Thiol-Ene Reactions in Material Science