Synthesis and self-assembly of bay-substituted perylene diimide gemini-type surfactants as off-on fluorescent probes for lipid bilayers

Jurgen Schill, Sam van Dun, Maarten J. Pouderoijen, Henk M. Janssen, Lech Gustav Milroy, Albertus P.H.J. Schenning, Luc Brunsveld

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

12 Citaten (Scopus)
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Samenvatting

Interest in bay-substituted perylene-3,4:9,10-tetracarboxylic diimides (PDIs) for solution-based applications is growing due to their improved solubility and altered optical and electronic properties compared to unsubstituted PDIs. Synthetic routes to 1,12-bay-substituted PDIs have been very demanding due to issues with steric hindrance and poor regioselectivity. Here we report a simple one-step regioselective and high yielding synthesis of a 1,12-dihydroxylated PDI derivative that can subsequently be alkylated in a straightforward fashion to produce nonplanar 1,12-dialkoxy PDIs. These PDIs show a large Stokes shift, which is specifically useful for bioimaging applications. A particular cationic PDI gemini-type surfactant has been developed that forms nonfluorescent self-assembled particles in water ("off state"), which exerts a high fluorescence upon incorporation into lipophilic bilayers ("on state"). Therefore, this probe is appealing as a highly sensitive fluorescent labelling marker with a low background signal for imaging artificial and cellular membranes.

Originele taal-2Engels
Pagina's (van-tot)7734-7741
Aantal pagina's8
TijdschriftChemistry : A European Journal
Volume24
Nummer van het tijdschrift30
Vroegere onlinedatum22 mrt 2018
DOI's
StatusGepubliceerd - 28 mei 2018

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