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Acylation of dipyrromethanes at the α and β positions and further development of fluorescent Zn2+ probes
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0001-6508-8355
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-1763-9383
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2014 (English)In: Sensors and actuators. B, Chemical, ISSN 0925-4005, Vol. 206, 291-302 p.Article in journal (Refereed) Published
Abstract [en]

The acylation of 5-aryl dipyrromethanes afforded products with interestingly rich substitution modes, i.e.; α- and β-monoacylated (modes a and b), and α, α′-, α, β′- and β, β′-diacylated (modes c-e). Especially, the β- and β, β′-acylation modes are unprecedented. And most of these products can be synthesized at a gram scale. The anisoyl substituted 5-(4-cyanophenyl) dipyrromethanes (1a-1e) were oxidized with DDQ. Thus, 1a and 1b afforded the corresponding dipyrrins 1a-DPR, and 1b-DPR. More interestingly, the diacylated ones 1c-1e could not be oxidized by DDQ. Instead, 1c-OH-1e-OH were obtained with a hydroxyl group attached to the 5-position. 1a-DPR-1e-OH were further developed as fluorescence turn-on Zn2+ probes. 1d-OH showed the highest sensitivity, with a detection limit of 1.5 × 10-8 M, and it was successfully applied in Zn2+ imaging in Hela cells. Furthermore, single crystals of two Zn2+ complexes were obtained and analyzed by X-ray diffraction.

Place, publisher, year, edition, pages
2014. Vol. 206, 291-302 p.
Keyword [en]
Acylation, Crystal structure, Dipyrromethane, Fluorescence probes
National Category
Theoretical Chemistry
URN: urn:nbn:se:kth:diva-161035DOI: 10.1016/j.snb.2014.09.060ISI: 000345234200101ScopusID: 2-s2.0-84907896014OAI: diva2:794630

QC 20150312

Available from: 2015-03-12 Created: 2015-03-06 Last updated: 2015-04-29Bibliographically approved

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Li, XinÅgren, Hans
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