Synthesis and characterization of nature inspired fluorophores

• Main Author: Deng, Boyuan
• Format: Dissertation
• Language: English
• Published: UCL (University College London) 2020

Oxyluciferin is the product of bioluminescence reaction of firefly luciferin. It has a highly conjugated structure and is non-toxici to animal cells. The thesis concerns the investigation of transforming the features of oxyluciferin into a bio-friendly fluorophore. The background and introduction chapters include how the fluorescence phenomenon has been discovered and a mechanistic explanation. It also covers several typical fluorophores and their applications. The second chapter starts from the design of keto and iminium derivatives of oxyluciferin with different electron-donating substituents. Then moves to their chemical synthesis includes direct condensation reaction between the corresponding ketone and dialkylamine. The third chapter covers the design of pyridine and pyridinium derivatives of oxyluciferin, the synthesis of which includes cyclisation methods of constructing thiazole and thiazolopyridine rings. Around 20 novel analogues have been successfully synthesized. The fourth part gives a brief description of optical properties of all the fluorophores prepared, includes some aggregation induced emission (AIE) fluorophores. The fluorescence of different analogues have nearly covered the entire visible light region. The bioconjugation reaction of the most promising fluorophore with an antibody illustrates the potential of its biological application. The final chapter contains detailed experimental procedures and charcacterisation data. The thesis is fully referenced to the primary literature.