KNCV Backer-prijs 2023
Youxin Fu wins the KNCV-Backer prize 2023
The KNCV-Backer Prize is awarded annually to the best PhD thesis in the field of organic chemistry that was defended in the Netherlands. The Committee consisted of Marthe Walvoort (Chair), Bauke Albada, Ronald Tennebroek and Rienk Eelkema; experts in a wide range of disciplines within the organic chemistry field.
In total, 17 theses were submitted this year. They were judged based on the scientific quality and their contributions to the field of organic chemistry, the impact of the research for science and society, and the clarity and structure of the thesis. The jury is impressed by the quality of all theses. From the first round in which each thesis was reviewed by two jury members, a sub-set of 5 theses was selected. After extensive deliberations, the jury has decided to award the 2023 KNCV Backer prize to Youxin Fu for his PhD-thesis titled ‘Phenanthrenequinone Photoclick Chemistry’. The study was conducted at the University of Groningen under the guidance of Profs. Ben Feringa and Wiktor Szymanski.
As organic chemists, most of us have gained intimate experience with at least one type of click reaction. Soon after the discovery of this conceptually new reaction, it found applications in research areas covering the entire spectrum between biology and materials. Whereas basic principles of most click reactions were excavated from sometimes ancient German literature, Dr. Fu successfully uncovered a light-triggered reaction that was initially performed under the Egyptian sun in August in 1943.[1]
In his thesis, Dr. Fu transformed this old photoclick reaction into an enabling reaction for rapid synthesis of instable 18F-radiolabeled conjugates to be used as PET tracers. He performed tedious reaction rate optimization by adjusting key structural features of the phenanthrenequinone and its reaction partners, achieving rates that are 1000-fold faster than the rates of the well-known strain-promoted alkyne-azide cycloaddition (SPAAC). Then, the potential limiting oxygen sensitivity of the original structure was addressed by appending thiophene rings, resulting in a significant expansion of the application areas, most notably in the realm of biological studies. In this process, quantum yields were also increased, up to 98%. His ambitions for the project were not yet satisfied, and Dr. Fu generated an orthogonal photo-click approach in combination with catalytic amounts of a photosensitizer so that activation of the phenanthrenequinone could be achieved using visible light. These developments were supported by computational analysis and transient spectroscopy in order to understand the mechanism and rationalize the next steps for improvement. The last chapter describes the fastest and most efficient near infrared-triggered photoclick reaction known to date. In short, with the developments of Dr. Fu, it can be expected that the mild photoclick reaction that is discovered will find widespread applications in various fields.
The outstanding quality of the synthetic work, the clearly written thesis, and the impact the results will have on the application of in situ-activated click reactions in biological systems and advanced materials convinced the jury to declare this thesis as the winner of the 2023 KNCV-Backer prize.
[1] A. Schönberg, A. Mustafa (1944) 'Photochemical Reactions. Part VIII. Reaction of ethylenes with phenanthraquinone' Journal of the Chemical Society, p. 387.
