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Click‐Connected 2‐(Hydroxyimino)aldehydes for the Design of UV‐Responsive Functional Molecules
Author(s) -
D'Acunzo Francesca,
Carbonaro Linda,
Cort Antonella Dalla,
Di Sabato Antonio,
Filippini Dario,
Leonelli Francesca,
Mancini Laura,
Gentili Patrizia
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001303
Subject(s) - chemistry , moiety , click chemistry , linker , cycloaddition , substituent , alkyne , combinatorial chemistry , aldehyde , triazole , molecule , photoisomerization , bioorthogonal chemistry , stereochemistry , organic chemistry , catalysis , isomerization , computer science , operating system
Click chemistry is used to functionalize simple lipophilic and water‐soluble molecules, a complex PEGylated phospholipid (DSPE‐PEG2000), and two benzylic substrates with the 2‐(hydroxyimino)aldehyde (HIA) group. To this end, two terminal alkynes bearing the HIA moiety were synthesized and coupled to different azides through copper(I)‐catalyzed azide alkyne cycloaddition (CuAAC). Norrish–Yang photoisomerization (λ= 365 nm, LED source) is successfully obtained, with no interference by the triazole linker, except when the forbidden n‐π* carbonyl transition is screened by a remote substituent such as salicylaldehyde. UV‐Vis spectrometry suggests a specific interaction of HIAs with Cu(II), whereas no such evidence is found with Cu(I). We thereby show that the CuAAC methodology can be used successfully to obtain HIA‐based UV‐responsive hydrophilic or lipophilic ligands, phospholipidic components for the construction of liposomes, and macrocycle precursors.