Functionalised polymers by surface modification using diaryl carbenes

Thesis

This thesis is concerned with the synthesis of diazo compounds for the introduction of various functional groups on the surface of polymers by means of carbene insertion and diazonium coupling. Characterisation and investigation of their properties were conducted.

A library of functionalised polystyrene beads containing pyridine rings has been established for the coordination of metal ions and metal complexes. The pyridyl system on the surface has demonstrated its capability to bind with zinc complexes of bis(thiosemicarbazones) and release the corresponding copper complexes upon transmetallation.

A spiropyran derivative has been introduced onto the surface of polystyrene and polyethylene terephthalate. The chromophore on both polymers exhibited photoswitchability as determined from colour change and wettability.

Polystyrenes with either pyridine or spiropyran units have been investigated for reversible immobilisation of bioactive species. Materials coated with penicillin V gave significant inhibition zones in antibacterial assays, showing efficacy in drug delivery.

Finally, a range of diazo compounds with different substituents has been synthesised and their thermal stabilities have been assessed by differential scanning calorimetry technique.

Authors: Aphaiwong, A

• Publication date: 2014
• DOI: 10.5287/ora-bxnngeymo
• Type of award: DPhil
• Level of award: Doctoral
• Awarding institution: University of Oxford
• Language: English
• Keywords: Polymer; modification.; surface
• Subjects: Organic chemistry