Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit
Marcia M, Singh P, Hauke F, Maggini M, Hirsch A (2014)
Publication Language: English
Publication Status: Published
Publication Type: Journal article, Original article
Publication year: 2014
Journal
Publisher: Royal Society of Chemistry
Book Volume: 12
Pages Range: 7045-7058
DOI: 10.1039/c4ob01007h
Abstract
The synthesis, characterization and metal complexation of a new class of perylene bisimides (PBIs) as an integral part of ethylenediaminetetraacetic acid (EDTA) are reported. The simplest representative, namely derivative 1a, was synthesized both by a convergent as well as a direct approach while the elongated derivatives, 1b and 1c, were obtained only via a convergent synthetic pathway. All these new prototypes of water-soluble perylenes are bolaamphiphiles and were fully characterized by H-1- and C-13-NMR spectroscopy, matrix assisted laser desorption ionization-time of flight (MALDI-TOF) mass spectrometry and IR spectroscopy. In order to acquaint ourselves with the behaviour in solution of our PBIs bearing dendritic wedges, the simplest derivative, 1a, was chosen and tested by means of UV/Vis and fluorescence spectroscopy as well as by zeta-potential measurements. A photoexcitation induced intramolecular photo-electron transfer (PET) can be observed in these molecules. Therefore their potential applications as sensors can be imagined. Model compound 1a efficiently coordinates trivalent metal cations both in water and dimethyl sulfoxide (DMSO). Significantly, the effects of the complexation strongly depend on the aggregation state of the PBI molecules in solution. As a matter of fact, in water, the presence of M3+ ions triggers the formation of light emitting supramolecular aggregates (excimers). On the other hand, in DMSO-rich solutions metal complexation leads to the suppression of the PET and leads to a strong fluorescence enhancement.
Authors with CRIS profile
Mario Marcia
Lehrstuhl für Organische Chemie II
Frank Hauke
Zentralinstitut für Neue Materialien und Prozesstechnik
Andreas Hirsch
Lehrstuhl für Organische Chemie II
Involved external institutions
Italy (IT)How to cite
APA:
Marcia, M., Singh, P., Hauke, F., Maggini, M., & Hirsch, A. (2014). Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit. Organic & Biomolecular Chemistry, 12, 7045-7058. https://doi.org/10.1039/c4ob01007h
MLA:
Marcia, Mario, et al. "Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit." Organic & Biomolecular Chemistry 12 (2014): 7045-7058.
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