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Irreversible Bleaching of Donor–Acceptor Stenhouse Adducts on the Surfaces of Magnetite Nanoparticles
Author(s) -
Ahrens Johannes,
Bian Tong,
Vexler Tom,
Klajn Rafal
Publication year - 2017
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201700009
Subject(s) - moiety , nanoparticle , chemistry , adduct , catechol , alkyl , molecule , acceptor , kinetics , magnetite nanoparticles , photochemistry , combinatorial chemistry , organic chemistry , magnetic nanoparticles , materials science , nanotechnology , physics , quantum mechanics , condensed matter physics
Two novel donor–acceptor Stenhouse adducts (DASAs) featuring the catechol moiety were synthesized and characterized. Both compounds bind strongly to the surfaces of magnetite nanoparticles. An adrenaline‐derived DASA renders the particles insoluble in all common solvents, likely because of poor solvation of the zwitterionic isomer generated on the nanoparticle surfaces. Well‐soluble nanoparticles were successfully obtained using dopamine‐derived DASA equipped with a long alkyl chain. Upon its attachment to nanoparticles, this DASA undergoes an irreversible decoloration reaction owing to the formation of the zwitterionic form. The reaction follows first‐order kinetics and proceeds more rapidly on large nanoparticles. Interestingly, decoloration can be suppressed in the presence of free DASA molecules in solution or at high nanoparticle concentrations.