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Ratiometric turn-on fluorophore displacement ensembles for nitroaromatic explosives detection

Authors
Lee, Ji YoonRoot, H.D.Ali, R.An, W.Lynch, V.M.Bähring, S.Kim, I.S.Sessler, J.L.Park, Jung Su
Issue Date
Nov-2020
Publisher
American Chemical Society
Citation
Journal of the American Chemical Society, v.142, no.46, pp.19579 - 19587
Journal Title
Journal of the American Chemical Society
Volume
142
Number
46
Start Page
19579
End Page
19587
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/1672
DOI
10.1021/jacs.0c08106
ISSN
0002-7863
Abstract
There is a recognized need in the area of explosives detection for fluorescence-based sensing systems that are capable of not only producing a turn-on response but also generating a distinctive spectral signature for a given analyte. Here, we report several supramolecular ensembles displaying efficient fluorophore displacement that give rise to an increase in fluorescence intensity upon exposure to various nitroaromatic compounds. The synthetic supramolecular constructs in question consist of a tetrathiafulvalene (TTF)-based pyrrolic macrocycle, benzo-TTF-calix[4]pyrrole (Bz-TTF-C4P), and fluorescent dyes, monomeric or dimeric naphthalenediimide (NDI) and perylenediimide (PDI) derivatives, as well as chloride or hexafluorophosphate (PF6-) salts of rhodamine 6G (Rh-6G). In chloroform solution, these assemblies exist in the form of discrete supramolecular complexes or oligomeric aggregates depending on the specific dye combinations in question. Each ensemble was tested as a potential explosive-responsive fluorescence indicator displacement assay (FIDA) by challenging it with a series of di- and trinitroaromatic compounds and examining the change in fluorescence spectral characteristics. Upon addition of nitroaromatic compounds (NACs), either a turn-onor a turn-offfluorescent response was observed depending on the nature of the constituent fluorophore and, where applicable, the counteranion. The FIDAs based on the PDI derivatives were found to display not only a ratiometric fluorescence enhancement but also analyte-dependent spectral changes when treated with NACs. The NAC-induced fluorescence spectral response of each ensemble was rationalized on the basis of various solution-phase spectroscopic studies, as well as single-crystal X-ray diffraction analyses. © 2020 American Chemical Society.
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