Abogunrin, Anthony A. and Healy, Stephen A. and Fenelon, Orla and Elmes, Robert B.P. (2022) Head vs. Tail Squaramide–Naphthalimide Conjugates: Self-Assembly and Anion Binding Behaviour. Chemistry, 4 (4). pp. 1288-1299. ISSN 2624-8549

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Abstract

The syntheses of two squaramide–naphthalimide conjugates (SN1 and SN2) are reported; the structures of SN1 and SN2 differ by the attachment of a squaramide—either at the ‘head’ or the ‘tail’ of the naphthalimide fluorophore. Both compounds displayed weak fluorescence due to the inclusion of a nitro-aromatic squaramide which efficiently quenches the emission of the naphthalimide. Both compounds were also shown to undergo self-aggregation as studied by 1H NMR and scanning electron microscopy (SEM). Furthermore, SN1 and SN2 gave rise to stark colourimetric changes in response to basic anions such as AcO−, SO4 2− HPO4 2−, and F−. The observed colour changes are thought to be due to deprotonation of a squaramide NH. The same basic anions also result in a further quenching of the naphthalimide emission. No colour change or emission modulations were observed in the presence of Cl−; however, 1H N

Item Type:	Article
Keywords:	supramolecular chemistry; squaramide; 1,8-naphthalimide; sensor; anion recognition; aggregation;
Academic Unit:	Faculty of Science and Engineering > Chemistry
Item ID:	18579
Identification Number:	https://doi.org/10.3390/chemistry4040085
Depositing User:	Robert Elmes
Date Deposited:	23 May 2024 14:19
Journal or Publication Title:	Chemistry
Publisher:	MDPI
Refereed:	Yes
URI:	Publisher
Use Licence:	This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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