Azadibenzocyclooctyne (ADIBO) is an efficient reagent for strain-promoted azide-alkyne cycloaddition (SPAAC) with long shelf life and high reactivity towards azides even in aqueous solutions. This dissertation is focused on the design, synthesis, and application of ADIBO derivatives. Alginates are a family of natural linear polysaccharides that become extremely important due to their ability to form hydrogels under mild conditions. Alginate hydrogels are widely used for cell culture and wound dressing as drug delivery system. A bis-ADIBO crosslinker was designed to achieve in situ crosslinking of azide-decorated alginate. The resulting hydrogels showed the potential application in tissue engineering. A cyclopropenone-masked ADIBO (photo-ADIBO) has also been developed, which can be deprotected by UV irradiation and revealed the ADIBO. A photo-ADIBO-ADIBO crosslinker was built to initiate the azide-decorated alginate crosslinking by photo-activation. The resulting hydrogels might be used for cell culture and wound dressing material. The ADIBO was also decorated with O-Naphthoquinone Methide Precursors (o-NQMP) to synthesize photocleavable amphiphilic block polymer. This material can be a potential candidate for the development of drug delivery micelles.
