Fotochemické konjugační a uvolňovací reakce na bázi ortho-chinon methidů

Masárová, Petra

Numerous photochemical reactions that form stable adducts are known, particularly in the context of conjugating moieties of biological or synthetic significance (e.g., photoaffinity labelling). Their main attribute is resistance to reversible cleavage, allowing persistence even in complex environments. However, the dynamic behaviour of a flexible system can also be exploited, for example in targeted delivery. Creating such a flexible system requires a specific scaffold, and in this work, we aim to investigate ortho-quinone methides (oQMs) as species that meet this demand. This thesis focuses on the "catch" stage - nucleophilic additions to the oQM scaffold. The influence of benzylic substitution of oQM as well as the choice of nucleophile on reaction yield and purity was examined, finding butyl-derived precursors and BuSH, PhNH2, and EtOH as the most promising reaction partners. In contrast, certain nucleophiles, particularly aliphatic or cyclic amines (BuNH2, pyrrolidine) and the phenyl-substituted precursor of oQM, gave inefficient or unselective outcomes with extensive side-product formation. Selected adducts were isolated and characterised from batch reactions. However, as is common for photochemical reactions, scaling up in batch led to reduced reactivity. To overcome these limitations, a flow...

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