Fluorescent asymmetric bis-ureas for pyrophosphate recognition in pure water

Casula, Arianna; Bazzicalupi, Carla; Bettoschi, Alexandre; Cadoni, Enzo; Coles, Simon J.; Isaia, Francesco; Lippolis, Vito; Mapp, Lucy K.; Marini, Giada M.; Montis, Riccardo; Scorciapino, Mariano Andrea; Caltagirone, Claudia

doi:10.1039/c5dt04497a

Cited by 18 publications

(13 citation statements)

References 39 publications

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“…Molecules that selectively change their color or fluorescence in the presence of anionic species are highly appealing for applications in various branches of science, industry and medicine [ 1 ]. Such changes may be induced by hydrogen bonding interactions with anions, especially in cases where hydrogen bond donors are directly coupled with the receptor’s chromophores or fluorophores [ 2 , 3 , 4 , 5 , 6 , 7 ]. If these changes are sufficiently strong and affect the visible region of the spectra, they can even be detected by naked eye [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

Carbazole-Based Colorimetric Anion Sensors

et al. 2021

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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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Section: Introductionmentioning

confidence: 99%

Carbazole-Based Colorimetric Anion Sensors

et al. 2021

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“…Molecules that selectively change their colour or fluorescence in response to anionic species are highly appealing for applications in many branches of science, industry and medicine [1]. Such changes may be induced by hydrogen bonding interactions with anions, especially in cases where hydrogen bond donors are directly coupled with the receptor's chromophores or fluorophores [2][3][4][5][6][7]. If these changes are sufficiently strong and affect visible part of the spectra, they may even be detected by naked eye [2].…”

Section: Introductionmentioning

confidence: 99%

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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“…Anions recognition and sensing have become one of the extremely promising topics in current research [3,4]. Recently, considerable effort has been devoted to the design of probes that have the ability to selectively bind and recognize biologically essential anions with the output of spectra signals [5][6][7][8]. Biological phosphate anions, such as adenosine triphosphate (ATP), adenosine diphosphate (ADP), and adenosine monophosphate (AMP), were essential to control the cellular movements and metabolic processes in the living organisms [9,10].…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of a Dinuclear Copper(II) Probe for Selective Fluorescence Sensing of Pyrophosphate

Liu

et al. 2019

Journal of Sensors

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A novel coumarin-based compound DPAC with two dipicolylamine (DPA) arms as the chelator sites was designed and synthesized. The compound DPAC exhibits a highly selective response to Cu2+ ions with a distinctly emission-quenching phenomenon. Moreover, the in situ formed complex DPAC-Cu2+ was used for the detection of pyrophosphate (PPi). The binding manner of probe DPAC-Cu2+ with PPi in 1 : 1 stoichiometry was supported by the Benesi-Hildebrand fitting, ESI-MS and HPLC analysis. The linear range of PPi concentration was 1-4 μM, and the detection limit was 0.53 μM. The competing experiments illustrated that the probe DPAC-Cu2+ had good sensitivity and selectivity for PPi than other anions, including ATP, ADP, AMP, and Pi in CH3CN : HEPES (3 : 2, v/v, pH=7.20) buffer. Further, cell fluorescence imaging experiments indicated that the probe DPAC-Cu2+ had a potential to be used to detect PPi in vivo.

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Fluorescent asymmetric bis-ureas for pyrophosphate recognition in pure water

Cited by 18 publications

References 39 publications

Carbazole-Based Colorimetric Anion Sensors

Carbazole-Based Colorimetric Anion Sensors

Carbazole-Based Colorimetric Anion Sensors

Design and Synthesis of a Dinuclear Copper(II) Probe for Selective Fluorescence Sensing of Pyrophosphate

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