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Issue 8, 2018
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Pyridine/pyridinium symmetrical bisamides as functional materials: aggregation, selective sensing and drug release

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Abstract

Pyrrole and furan-based pyridine/pyridinium bisamides 1–4 have been designed and synthesized with a view to establishing new supramolecular gelators. The neutral gelators 1 and 2 were explored for cation binding. While the furan analogue 1 forms gel in the presence of Ag+ and Cu2+ ions in DMSO : H2O (1 : 1, v/v), the pyrrole conjugate 2 exhibits metallogel formation selectively with Ag+ ions and corroborates the role of the heteroatom in the spacer that modulates the self assembly behavior of the gelators. As an application, the 1-Cu gel selectively distinguishes thiol-based amino acids from a series of other amino acids as well as effectively discriminates D-glucose from its C2-epimer D-mannose by exhibiting gel to sol transformation. Additionally, encapsulation and subsequent release of the chemopreventive drug curcumin has been studied using the 1-Cu gel. Placement of a cholesterol unit onto the structures 1 and 2 resulted in charged structures 3 and 4 of which compound 4 produced an unambiguous visual readout of F and AcO ions by showing gel to sol transition.

Graphical abstract: Pyridine/pyridinium symmetrical bisamides as functional materials: aggregation, selective sensing and drug release

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Publication details

The article was received on 12 Oct 2017, accepted on 08 Mar 2018 and first published on 09 Mar 2018


Article type: Paper
DOI: 10.1039/C7NJ03931J
Citation: New J. Chem., 2018,42, 6488-6497
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    Pyridine/pyridinium symmetrical bisamides as functional materials: aggregation, selective sensing and drug release

    S. Panja, S. Ghosh and K. Ghosh, New J. Chem., 2018, 42, 6488
    DOI: 10.1039/C7NJ03931J

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