Advances in fluorescent and colorimetric sensors for anionic species

McNaughton, Daniel A.; Farès, Mohamed; Picci, Giacomo; Gale, Philip A.; Caltagirone, Claudia

doi:10.1016/j.ccr.2020.213573

Cited by 93 publications

(62 citation statements)

References 147 publications

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“…very similar for all basic anions. Similar behaviour is commonly observed in many hydrogen bonding anion sensors [9].…”

Section: Anion Sensing Properties Of 3 Andsupporting

confidence: 83%

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Carbazole-Based Colorimetric Anion Sensors

Maslowska-Jarzyna¹,

Korczak²,

Wagner³

et al. 2021

Preprint

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Endowed with strong carbazole chromophore and fluorophore as well as with powerful and convergent hydrogen bond donors, 1,8-diaminocarbazoles are amongst the most attractive and synthetically versatile building blocks for the construction of anion receptors, sensors and transporters. Aiming at the development of carbazole-based colorimetric anion sensors, we describe here the synthesis of 1,8-diaminocarbazoles substituted with strongly electron-withdrawing substituents: 3,6-dicyano and 3,6-dinitro. Both of these precursors were subsequently converted into model diamide receptors. Anion binding studies revealed that the new receptors show greatly enhanced anion affinity, but also significantly increased acidity. We found also that rear substitution of 1,8-diamidocarbazole with two nitro groups shifts its absorption spectrum to the visible region and converts receptor into colorimetric anion sensor. The new sensor produces vivid changes in colour and fluorescence upon addition of basic anions in wet DMSO, but is poorly selective: due to its greatly enhanced acidity, for most anions the dominant receptor-anion interaction is proton transfer and, accordingly, similar changes in colour can be observed for every basic anion. The highly acidic and strongly binding receptors developed in this study may find applications in organocatalysis or in pH-switchable anion transport through lipophilic membranes.

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“…very similar for all basic anions. Similar behaviour is commonly observed in many hydrogen bonding anion sensors [9].…”

Section: Anion Sensing Properties Of 3 Andsupporting

confidence: 83%

“…If these changes are sufficiently strong and affect visible part of the spectra, they may even be detected by naked eye [2]. Significant research efforts have therefore been directed towards the development of colorimetric and fluorescent anion sensors based on hydrogen bond donating receptors [8][9].…”

Section: Introductionmentioning

confidence: 99%

Carbazole-Based Colorimetric Anion Sensors

Maslowska-Jarzyna¹,

Korczak²,

Wagner³

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

“…As a result, the colorimetric response of 4 exhibited low specificity, i.e., it was very similar for all basic anions. Analogous behavior has often been observed in hydrogen bonding anion sensors [ 9 ].…”

Section: Resultsmentioning

confidence: 54%

“…If these changes are sufficiently strong and affect the visible region of the spectra, they can even be detected by naked eye [ 2 ]. Significant research efforts have therefore been directed towards the development of colorimetric and fluorescent anion sensors based on hydrogen bond donating receptors [ 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

Carbazole-Based Colorimetric Anion Sensors

et al. 2021

View full text Add to dashboard Cite

Owing to their strong carbazole chromophore and fluorophore, as well as to their powerful and convergent hydrogen bond donors, 1,8-diaminocarbazoles are amongst the most attractive and synthetically versatile building blocks for the construction of anion receptors, sensors, and transporters. Aiming to develop carbazole-based colorimetric anion sensors, herein we describe the synthesis of 1,8-diaminocarbazoles substituted with strongly electron-withdrawing substituents, i.e., 3,6-dicyano and 3,6-dinitro. Both of these precursors were subsequently converted into model diamide receptors. Anion binding studies revealed that the new receptors exhibited significantly enhanced anion affinities, but also significantly increased acidities. We also found that rear substitution of 1,8-diamidocarbazole with two nitro groups shifted its absorption spectrum into the visible region and converted the receptor into a colorimetric anion sensor. The new sensor displayed vivid color and fluorescence changes upon addition of basic anions in wet dimethyl sulfoxide, but it was poorly selective; because of its enhanced acidity, the dominant receptor-anion interaction for most anions was proton transfer and, accordingly, similar changes in color were observed for all basic anions. The highly acidic and strongly binding receptors developed in this study may be applicable in organocatalysis or in pH-switchable anion transport through lipophilic membranes.

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“…Hence, the success of such research relies on the design of water‐soluble organic ligands forming metal complexes with high thermodynamic and kinetic stability, the introduction of supplementary supramolecular interactions with the substrate to increase selectivity, and the availability of at least one coordination site of the metal for the interaction with the anion. Facing these issues can lead to selective and strong binding applicable for anion sensing in competitive media [7,8] . Indeed, metal complexes that use Lewis acid‐base interactions to bind anions in water are a good answer to the problem since water is a strong hydrogen bonding agent, but a relatively poor Lewis base, lowly interfering with the recognition process as we also demonstrated in our previous papers [9,10] .…”

Section: Figurementioning

confidence: 67%

A Newly Designed Water Soluble Uranyl‐Salophen Complex for Anion Recognition

et al. 2021

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A novel water‐soluble uranyl‐salophen (salophen=N,N‘‐disalicylidene‐o‐phenylenediaminate) complex was obtained. Solubility was achieved in aqueous methyl‐β‐cyclodextrin solutions, taking advantage of the host‐guest interactions established with the adamantyl moieties present on the ligand skeleton. Such an approach facilitates the synthesis of the receptor and the purification processes and, in perspective, can be definitely applicable to other molecular scaffolds. UV/Vis titration experiments demonstrate that the capacity of the uranyl‐salophen core to behave as a receptor for anions is retained in water and appears comparable with that previously reported for other water‐soluble uranyl‐salophen systems. Hence the presence of cyclodextrins does not interfere with molecular recognition processes.

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Advances in fluorescent and colorimetric sensors for anionic species

Cited by 93 publications

References 147 publications

Carbazole-Based Colorimetric Anion Sensors

Carbazole-Based Colorimetric Anion Sensors

Carbazole-Based Colorimetric Anion Sensors

A Newly Designed Water Soluble Uranyl‐Salophen Complex for Anion Recognition

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