Highly sensitive and selective molecular probes for chromo-fluorogenic sensing of carbon monoxide in air, aqueous solution and cells

Anita Toscani, Cristina Marín-Hernández, Jonathan Robson, Elvin Chua, Paul Dingwall, Andrew White, Félix Sancenón, Cristina de la Torre, Ramón Martínez-Máñez, James Wilton-Ely

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Abstract

Optical sensing offers a low-cost and effective means to sense carbon monoxide in air and in solution. This contribution reports the synthesis of a new series of vinyl complexes [Ru(CH=CHR)Cl(CO)(TBTD)(PPh3)2] (R = aryl, TBTD = 5-(3-thienyl)-2,1,3-benzothiadiazole) and shows them to be highly sensitive and selective probes for carbon monoxide in both solution and air. Depending on the vinyl substituent, chromogenic and fluorogenic responses signalled the presence of this invisible, odourless, tasteless and toxic gas. Adsorbing the complexes on silica produced colorimetric probes for the 'naked eye' detection of CO in the gas phase with a limit of detection as low as 8 ppm in some cases, while the release of the TBTD fluorophore allowed detection at much lower concentrations through the fluorescence response. Structural data were obtained by single crystal X-ray diffraction techniques, while the photophysical behaviour was explored computationally using TD-DFT experiments. The systems were also shown to be selective for CO over all other gases tested, including water vapour and common organic solvents. By introducing a poly(ethylene)glycol chain to the vinyl functionality, water compatibility was achieved and these non-cytotoxic complexes were employed in the sensing of CO in HeLa cells, offering a simple and rapid system for sensing this gasotransmitter in this challenging medium.

Original languageEnglish
JournalChemistry-a European Journal
Early online date23 Nov 2018
DOIs
Publication statusPublished - 09 Jan 2019
Externally publishedYes

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© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Toscani, A., Marín-Hernández, C., Robson, J., Chua, E., Dingwall, P., White, A., Sancenón, F., de la Torre, C., Martínez-Máñez, R., & Wilton-Ely, J. (2019). Highly sensitive and selective molecular probes for chromo-fluorogenic sensing of carbon monoxide in air, aqueous solution and cells. Chemistry-a European Journal. https://doi.org/10.1002/chem.201805244