Exciplex formation as an approach to selective Copper(II) fluorescent sensors

Correia, Bruna; Brown, Thomas R.; Reibenspies, Joseph H.; Lee, Hee-Seung; Hancock, Robert D.

doi:10.1016/j.ica.2020.119544

Cited by 6 publications

(5 citation statements)

References 59 publications

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“…In the case of fluorophore-substituted cyclens, fluorescent complexes where excimers formed were reported. − We also reported tetra-armed cyclens ( L a – L c ) with fluorophore as side arms and their silver(I) complexes. However, in the silver(I) complexes of cyclens L a – L c , the excimer formation was not observed even if fluorophores have existed in the side arms. , It is considered that the formation of excimer has been difficult due to the steric hindrance when the complex formed the silver(I) complex.…”

Section: Introductionmentioning

confidence: 91%

Argentivorous Molecules with Chromophores in Side Arms: Silver Ion-Induced Turn On and Turn Off of Fluorescence

Taniguchi

Kikukawa

et al. 2021

Inorg. Chem.

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The synthesis of argentivorous molecules (L1 and L2 ) having two chromophores (4-(anthracen-9-yl)benzyl or 4-(pyren-1-yl)benzyl groups) and two benzyl groups and the fluorescence properties of their silver complexes in a solution and the solid state are reported. A crystallographic approach for the Ag+ complexes with L1 and L2 revealed that the observed fluorescence changes stem from the excimer formation and extinction of fluorescent. Furthermore, binding stabilities of L1 and L2 toward Ag+ ions were estimated by the Ag+-induced UV–vis and PL spectral changes.

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Section: Introductionmentioning

confidence: 91%

Argentivorous Molecules with Chromophores in Side Arms: Silver Ion-Induced Turn On and Turn Off of Fluorescence

Taniguchi

Kikukawa

et al. 2021

Inorg. Chem.

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“…It was observed that in the presence of Zn 2+ , the fluorescence intensity was enhanced ≈16-fold (Figure ). The enhancement of fluorescence intensity (Φ = 0.14) with the addition of Zn 2+ is probably due to the π–π stacking of pyrene moieties and the formation of a static exciplex . However, titration of the probe with Zn 2+ in CH 3 CN showed an interesting result.…”

Section: Resultsmentioning

confidence: 98%

“…The enhancement of fluorescence intensity (Φ = 0.14) with the addition of Zn 2+ is probably due to the π–π stacking of pyrene moieties and the formation of a static exciplex. 69 However, titration of the probe with Zn 2+ in CH 3 CN showed an interesting result. A substantial increase in the fluorescence intensity at the 527 nm band was witnessed until the [Zn 2+ ]/[ PMHMP ] mole ratio reached 0.5 ( I / I 0 ratio is ≈ 16), followed by fluorescence quenching.…”

Section: Resultsmentioning

confidence: 99%

Dual-Mode Multiple Ion Sensing via Analyte-Specific Modulation of Keto–Enol Tautomerization of an ESIPT Active Pyrene Derivative: Experimental Findings and Computational Rationalization

2023

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A pyrene-based e xcited - state intramolecular proton transfer (ESIPT) active probe PMHMP was synthesized, characterized, and employed for the ppb-level, dual-mode, and high-fidelity detection of Cu2+ (LOD: 7.8 ppb) and Zn2+ ions (LOD: 4.2 ppb) in acetonitrile medium. The colorless solution of PMHMP turned yellow upon the addition of Cu2+, suggesting its ratiometric, naked-eye sensing. On the contrary, Zn2+ ions displayed concentration-dependent fluorescence rise till a 0.5 mole fraction and subsequent quenching. Mechanistic investigations indicated the formation of a 1:2 exciplex (Zn2+:PMHMP) at a lower concentration of Zn2+, which eventually turned into a more stable 1:1 (Zn2+:PMHMP) complex with an additional amount of Zn2+ ions. However, in both cases, it was observed that the hydroxyl group and the nitrogen atom of the azomethine unit were involved in the metal ion coordination, which eventually altered the ESIPT emission. Furthermore, a green-fluorescent 2:1 PMHMP–Zn2+ complex was developed and additionally employed for the fluorimetric analysis of both Cu2+ and H2PO4 – ions. The Cu2+ ion, owing to its higher binding affinity for PMHMP, could replace the Zn2+ ion from the preformed complex. On the other hand, H2PO4 – formed a tertiary adduct with the Zn2+–complex, leading to a distinguishable optical signal. Furthermore, extensive and organized density functional theory calculations were performed to explore the ESIPT behavior of PMHMP and the geometrical and electronic properties of the metal complexes.

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“…Cyclen is a 12-membered cyclic polyamine which forms stable complexes with transition-metal ions as well as main group metal ions. − To enhance the coordination ability and applicability, substituted cyclens in which functional groups or macrocycles were adopted in the cyclen amine part were reported, and their complexes were determined. − For example, Hancock et al have reported lead(II), copper(II), silver(I), and cadmium(II) complexes of di( N -benzyl)cyclen. Using cadmium(II) complex, the selective fluorescence sensor for the chloride anion was investigated .…”

Section: Introductionmentioning

confidence: 99%

Mole-Ratio-Dependent Reversible Transformation between 2:2 and Cyclic 3:6 Silver(I) Complexes with an Argentivorous Molecule

Abe

Takahashi

et al. 2021

Inorg. Chem.

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A tetra-armed cyclen (L) with two substituted 3,5-difluorobenzyl and two substituted pyridine-4-yl methyl groups at the 1,4- and 7,10-positions of the cyclen ring as side arms was synthesized. When L was reacted with 1 equiv of the silver(I), dimetallo[3.3]paracyclophane-like 2:2 cyclic dimer, [Ag2(L)2](PF6)2, was obtained. The reaction of L with 2 equiv of silver(I) gave a 3:6 cyclic trimer, [Ag6(L)3(CH3CN)3](OTf)6·3CH3CN. Furthermore, reversible complexation between the 2:2 cyclic dimer and 3:6 cyclic trimer was confirmed by 1H NMR and the CSI mass in the addition of silver(I) or the [2.2.2]cryptand.

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Exciplex formation as an approach to selective Copper(II) fluorescent sensors

Cited by 6 publications

References 59 publications

Argentivorous Molecules with Chromophores in Side Arms: Silver Ion-Induced Turn On and Turn Off of Fluorescence

Argentivorous Molecules with Chromophores in Side Arms: Silver Ion-Induced Turn On and Turn Off of Fluorescence

Dual-Mode Multiple Ion Sensing via Analyte-Specific Modulation of Keto–Enol Tautomerization of an ESIPT Active Pyrene Derivative: Experimental Findings and Computational Rationalization

Mole-Ratio-Dependent Reversible Transformation between 2:2 and Cyclic 3:6 Silver(I) Complexes with an Argentivorous Molecule

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