A ferrocene–pyrene based ‘turn-on’ chemodosimeter for Cr<sup>3+</sup>– application in bioimaging

Kaur, Mandeep; Kaur, Paramjit; Dhuna, Vikram; Singh, Sukhdev; Singh, Kamaljit

doi:10.1039/c3dt53536c

Cited by 53 publications

(23 citation statements)

References 36 publications

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“…It is well known that fluorescent turn-on chemosensors are preferable due to their highly selectivity, sensitivity and ease of observation [35][36][37] . The enhanced fluorescence response of chemosensor 3 when binding Cr 3+ could be attributed to an interference of both intra-molecular charge transfer (ICT) and chelation energy transfer (CHEF).…”

Section: Fluorescence Recognition Mechanismmentioning

confidence: 99%

A fast-response, fluorescent ‘turn-on’ chemosensor for selective detection of Cr³⁺

et al. 2015

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A fast-response, highly selective and sensitive chemosensor, 3, for Cr 3+ detection with turn-on fluorescence behavior in the physiological pH range was designed and synthesized. The chemosensor contained a combined push-pull system in which the fluorescent phenanthro[9,10-d]oxazole moiety acts as both the electron donor and a potential binding site. An electron deficient nitrile group served as the electron acceptor. A significant enhancement of fluorescene emission intensities was observed with increasing Cr 3+ concentration upon excition at 300 nm. The emission intensity reached its maximum on adding 8 equiv. of Cr 3+ where the quantum yield of 3-Cr 3+ was found to be 0.917, ca. 7-fold larger than the chemosensor 3.The selectivity mechanism of 3 for Cr 3+ was found to be based on the combined effects of the inhibition of ICT and CHEF. Remarkably the entire process was virtually complete in only 10 seconds, with a minimum detection limit for Cr 3+ of 1.72 × 10 -8 M -1 .

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Section: Fluorescence Recognition Mechanismmentioning

confidence: 99%

A fast-response, fluorescent ‘turn-on’ chemosensor for selective detection of Cr³⁺

et al. 2015

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“…The high degree of π-electron delocalization and rigid molecular backbone of pyrene bring about fascinating electronic and photophysical properties, such as strong fluorescence and the tendency for the formation of excimers in the excited state. [6,7] These properties render pyrene a widely used fluorophore in fluorescence sensing, [8][9][10][11] bioimaging, [12][13][14][15] electroluminescence devices, [16][17][18] and so on. The synthetic chemistry of pyrene derivatives has been well developed over the past few decades, which in turn has greatly expanded the application of pyrene-based materials.…”

Section: Introductionmentioning

confidence: 99%

Comparative studies of the noncovalent interactions in the single‐crystal packing of pyrene, pyrene‐4,5‐dione, and pyrene‐4,5,9,10‐tetraone

Zreid

Tabasi

Zhao

2021

J of Physical Organic Chem

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Pyrene-4,5-dione and pyrene-4,5,9,10-tetraone are K-region oxidized derivatives of pyrene, which show interesting structural and electronic properties as well as useful application in organic electronic and optoelectronic devices. The single-crystal structures of pyrene and pyrene-4,5-dione have been published, but the crystallographic data of pyrene-4,5,9,10-tetraone has not. In this work, the single-crystal structure of pyrene-4,5,9,10-tetraone has been clearly elucidated for the first time, and the detailed crystallographic properties were analyzed and discussed in comparison with those of pyrene and pyrene-4,5-dione. Various noncovalent interactions taking place within the supramolecular assemblies that exist in the crystal packing of these compounds were studied by Hirshfeld surface analysis and density functional theory (DFT) calculations. Our joint experimental and computational analyses provide fundamental understanding of the electron density properties, interaction energies, and frontier molecular orbital (FMO) properties for these pyrene systems and establish correlations of these properties with diverse supramolecular assembling motifs.

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“…In recent years, mono-core ferrocene and its derivatives have been revealed to be very convenient building blocks for redox-active receptors used for cation and anion recognition. [20][21][22][23][24][25][26] For example, Molina and co-workers reported a ferrocene-based ion pair receptor that only recognized the HSO 4 − anion in the presence of Pb 2+ or Zn 2+ , whereas no affinity to the free receptor by the HSO 4 − anion is observed. 27 However, since ferrocene is a known fluorescence quenching group, receptors based on multi-core ferrocene recognizing ions by fluorescence enhancement have been rarely reported.…”

Section: Introductionmentioning

confidence: 99%

A simple and highly selective 2,2-diferrocenylpropane-based multi-channel ion pair receptor for Pb²⁺ and HSO₄⁻

et al. 2015

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A structurally simple, 2,2-diferrocenylpropane-based ion pair receptor 1 was synthesized and characterized by (1)H NMR, (13)C NMR, HRMS, elemental analyses, and single-crystal X-ray diffraction. The ion pair receptor 1 showed excellent selectivity and sensitivity towards Pb(2+) with multi-channel responses: a fluorescence enhancement (more than 42-fold), a notable color change from yellow to red, redox anodic shift (ΔE1/2 = 151 mV), while HSO4(-) promoted fluorescence enhancement when Pb(2+) or Zn(2+) was bonded to the cation binding-site. (1)H NMR titration and density functional theory were performed to reveal the sensing mechanism based on photo-induced electron transfer (PET).

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A ferrocene–pyrene based ‘turn-on’ chemodosimeter for Cr³⁺– application in bioimaging

Cited by 53 publications

References 36 publications

A fast-response, fluorescent ‘turn-on’ chemosensor for selective detection of Cr³⁺

A fast-response, fluorescent ‘turn-on’ chemosensor for selective detection of Cr³⁺

Comparative studies of the noncovalent interactions in the single‐crystal packing of pyrene, pyrene‐4,5‐dione, and pyrene‐4,5,9,10‐tetraone

A simple and highly selective 2,2-diferrocenylpropane-based multi-channel ion pair receptor for Pb²⁺ and HSO₄⁻

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A ferrocene–pyrene based ‘turn-on’ chemodosimeter for Cr3+– application in bioimaging

Cited by 53 publications

References 36 publications

A fast-response, fluorescent ‘turn-on’ chemosensor for selective detection of Cr3+

A fast-response, fluorescent ‘turn-on’ chemosensor for selective detection of Cr3+

Comparative studies of the noncovalent interactions in the single‐crystal packing of pyrene, pyrene‐4,5‐dione, and pyrene‐4,5,9,10‐tetraone

A simple and highly selective 2,2-diferrocenylpropane-based multi-channel ion pair receptor for Pb2+ and HSO4−

Contact Info

Product

Resources

About

A ferrocene–pyrene based ‘turn-on’ chemodosimeter for Cr³⁺– application in bioimaging

A fast-response, fluorescent ‘turn-on’ chemosensor for selective detection of Cr³⁺

A fast-response, fluorescent ‘turn-on’ chemosensor for selective detection of Cr³⁺

A simple and highly selective 2,2-diferrocenylpropane-based multi-channel ion pair receptor for Pb²⁺ and HSO₄⁻