Irreversible bleaching of donor-acceptor stenhouse adducts on the surfaces of magnetite nanoparticles Ahrens, Johannes Bian, Tong Vexler, Tom Klajn, Rafal Organic Chemistry Physical and Theoretical Chemistry Analytical Chemistry 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. Wiley 2017 info:eu-repo/semantics/article doc-type:Article Article http://purl.org/coar/resource_type/c_2df8fbb1 https://research-explorer.ista.ac.at/record/13383 Ahrens J, Bian T, Vexler T, Klajn R. Irreversible bleaching of donor-acceptor stenhouse adducts on the surfaces of magnetite nanoparticles. <i>ChemPhotoChem</i>. 2017;1(5):230-236. doi:<a href="https://doi.org/10.1002/cptc.201700009">10.1002/cptc.201700009</a> eng info:eu-repo/semantics/altIdentifier/doi/10.1002/cptc.201700009 info:eu-repo/semantics/altIdentifier/e-issn/2367-0932 info:eu-repo/semantics/closedAccess