Squaramide-Based Reagent for Selective Chromogenic Sensing of Cu(II) through a Zwitterion Radical

Sanna, Elena; Martínez, Luis; Rotger, Carmen; Blasco, Salvador; González‐García, Jorge; Garcı́a-España, Enrique; Costa, Antoni

doi:10.1021/ol101514y

Cited by 62 publications

(17 citation statements)

References 44 publications

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“…We have collated a list of diverse organic neutral radicals , radical anions , radical cations and zwitterionic radicals [132][133][134][135][136] in Charts 1-3 according to the year of their report. It is to be noted that the list is not exhaustive.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Organic Radicals and Their Magnetism

et al. 2016

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Abstract:The review presents an overview of the organic radicals that have been designed and synthesized recently, and their magnetic properties are discussed. The π-conjugated organic radicals such as phenalenyl systems, functionalized nitronylnitroxides, benzotriazinyl, bisthiazolyl, aminyl-based radicals and polyradicals, and Tetrathiafulvalene (TTF)-based H-bonded radicals have been considered. The examples show that weak supramolecular interactions play a major role in modulating the ferromagnetic and antiferromagnetic properties. The new emerging direction of zethrenes, organic polyradicals, and macrocyclic polyradicals with their attractive and discrete architectures has been deliberated. The magnetic studies delineate the singlet-triplet transitions and their corresponding energies in these organic radicals. We have also made an attempt to collate the major organic neutral radicals, radical ions and radical zwitterions that have emerged over the last century.

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Section: Introductionmentioning

confidence: 99%

Recent Advances in Organic Radicals and Their Magnetism

et al. 2016

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“…Recently, radical based reagent with high selectivity and sensitivity for Cu 2+ is been reported in literature. 34,35 It provides an situ evaluation of solvated Cu 2+ in aqueous environments. Mukhopadhyay et al, 36 have reported for the rst time formation of a persistent radical cation of naphthalenediimide with Cu 2+ /Fe 3+ which exhibit panchromatic and NIR optical bands and can be used as multichannel probes.…”

Section: Introductionmentioning

confidence: 99%

A novel colorimetric and fluorogenic chemosensor for selective detection of Cu²⁺ ions in mixed aqueous media

et al. 2014

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“…In the past few years, many colorimetric and fluorescent chemosensors have been reported for sensing copper ions with absorbance and emission in the visible region. [10][11][12][13][14][15][16][17][18] Although chemosensors with visible (absorbance/emission) re-Abstract: We present novel Schiff base ligands julolidine-carbonohydrazone 1 and julolidine-thiocarbonohydrazone 2 for selective detection of Cu 2 + in aqueous medium. The planar julolidinebased ligands can sense Cu 2 + colorimetrically with characteristic absorbance in the near-infrared (NIR, 700-1000 nm) region.…”

Section: Introductionmentioning

confidence: 99%

Visible–Near‐Infrared and Fluorescent Copper Sensors Based on Julolidine Conjugates: Selective Detection and Fluorescence Imaging in Living Cells

Maity

Manna

Dhanasekaran

et al. 2011

Chemistry A European J

176

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We present novel Schiff base ligands julolidine-carbonohydrazone 1 and julolidine-thiocarbonohydrazone 2 for selective detection of Cu(2+) in aqueous medium. The planar julolidine-based ligands can sense Cu(2+) colorimetrically with characteristic absorbance in the near-infrared (NIR, 700-1000 nm) region. Employing molecular probes 1 and 2 for detection of Cu(2+) not only allowed detection by the naked eye, but also detection of varying micromolar concentrations of Cu(2+) due to the appearance of distinct coloration. Moreover, Cu(2+) selectively quenches the fluorescence of julolidine-thiocarbonohydrazone 2 among all other metal ions, which increases the sensitivity of the probe. Furthermore, quenched fluorescence of the ligand 2 in the presence of Cu(2+) was restored by adjusting the complexation ability of the ligand. Hence, by treatment with ethylenediaminetetraacetic acid (EDTA), thus enabling reversibility and dual-check signaling, julolidine-thiocarbonohydrazone (2) can be used as a fluorescent molecular probe for the sensitive detection of Cu(2+) in biological systems. The ligands 1 and 2 can be utilized to monitor Cu(2+) in aqueous solution over a wide pH range. We have investigated the structural, electronic, and optical properties of the ligands using ab initio density functional theory (DFT) combined with time-dependent density functional theory (TDDFT) calculations. The observed absorption band in the NIR region is attributed to the formation of a charge-transfer complex between Cu(2+) and the ligand. The fluorescence-quenching behavior can be accounted for primarily due to the excited-state ligand 2 to metal (Cu(2+)) charge-transfer (LMCT) processes. Thus, experimentally observed characteristic NIR and fluorescence optical responses of the ligands upon binding to Cu(2+) are well supported by the theoretical calculations. Subsequently, we have employed julolidine-thiocarbonohydrazone 2 for reversible fluorescence sensing of intracellular Cu(2+) in cultured HEK293T cells.

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Squaramide-Based Reagent for Selective Chromogenic Sensing of Cu(II) through a Zwitterion Radical

Cited by 62 publications

References 44 publications

Recent Advances in Organic Radicals and Their Magnetism

Recent Advances in Organic Radicals and Their Magnetism

A novel colorimetric and fluorogenic chemosensor for selective detection of Cu²⁺ ions in mixed aqueous media

Visible–Near‐Infrared and Fluorescent Copper Sensors Based on Julolidine Conjugates: Selective Detection and Fluorescence Imaging in Living Cells

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Squaramide-Based Reagent for Selective Chromogenic Sensing of Cu(II) through a Zwitterion Radical

Cited by 62 publications

References 44 publications

Recent Advances in Organic Radicals and Their Magnetism

Recent Advances in Organic Radicals and Their Magnetism

A novel colorimetric and fluorogenic chemosensor for selective detection of Cu2+ ions in mixed aqueous media

Visible–Near‐Infrared and Fluorescent Copper Sensors Based on Julolidine Conjugates: Selective Detection and Fluorescence Imaging in Living Cells

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Product

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A novel colorimetric and fluorogenic chemosensor for selective detection of Cu²⁺ ions in mixed aqueous media