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Syntheses of mono- and diacylated bipyrroles with rich substitution modes and development of a prodigiosin derivative as a fluorescent Zn(II) probe
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0001-6508-8355
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2014 (English)In: RSC Advances, ISSN 2046-2069, Vol. 4, no 12, 6133-6140 p.Article in journal (Refereed) Published
Abstract [en]

The acylation of 2,20-bipyrrole with pentafluorobenzoyl chloride in the presence of AlCl3 afforded six acylated products with rich alpha-, beta-, beta(1)-, alpha,alpha'-, alpha,beta(')-, and alpha,beta(1)'-substitution modes for 1-6, respectively. Then, the alpha,alpha'-diacylated compound 4 was used to synthesize a prodigiosin derivative 9, which provides an alternative method for the syntheses of prodigiosin derivatives. Crystal structures of 1, 4 and 9 show interesting supramolecular dimers formed by multiple hydrogen bonds, O...pi interactions, as well as pi... pi interactions. Interestingly, 9 shows fluorescence turn-on probing behavior towards Zn2+ both in DMF and in DMF-HEPES, with high sensitivity and selectivity. The detection limit for Zn2+ in DMF was calculated to be 1.1 x 10(-8) M.

Place, publisher, year, edition, pages
2014. Vol. 4, no 12, 6133-6140 p.
Keyword [en]
On Zn2+ Probes, Zinc Ions, Hexafluorobenzene Interaction, Pi Interactions, Cyanide Probes, Living Cells, Sensor, Bodipy, Porphyrin, Coumarin
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URN: urn:nbn:se:kth:diva-141320DOI: 10.1039/c3ra47277aISI: 000329865800044ScopusID: 2-s2.0-84892146566OAI: diva2:696703

QC 20140214

Available from: 2014-02-14 Created: 2014-02-13 Last updated: 2014-02-14Bibliographically approved

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