Dual responsive chemosensors for anions: the combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single molecule

Gunnlaugsson, Thorfinnur; Kruger, Paul E.; Lee, T.Clive; Parkesh, Raman; Pfeffer, Frederick M.; Hussey, Gillian M.

doi:10.1016/s0040-4039(03)01699-x

Cited by 224 publications

(78 citation statements)

References 31 publications

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“…50 Sensor 8a was developed in our laboratories and is based on the fluorophorespacer-receptor principle and was the first example of a naphthalimide-based anion sensor to include a hydrogenbonding receptor, Fig. 4 and 5.…”

Section: General Design Principles Employed In Colorimetric and Fluormentioning

confidence: 99%

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

et al. 2010

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This critical review focuses on the development of anion sensors, being either fluorescent and/or colorimetric, based on the use of the 1,8-naphthalimide structure; a highly versatile building unit that absorbs and emits at long wavelengths. The review commences with a short description of the most commonly used design principles employed in chemosensors, followed by a discussion on the photophysical properties of the 4-amino-1,8-naphthalimide structure which has been most commonly employed in both cation and anion sensing to date. This is followed by a review of the current state of the art in naphthalimide-based anion sensing, where systems using ureas, thioureas and amides as hydrogen-bonding receptors, as well as charged receptors have been used for anion sensing in both organic and aqueous solutions, or within various polymeric networks, such as hydrogels. The review concludes with some current and future perspectives including the use of the naphthalimides for sensing small biomolecules, such as amino acids, as well as probes for incorporation and binding to proteins; and for the recognition/sensing of polyanions such as DNA, and their potential use as novel therapeutic and diagnostic agents (95 references).

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Section: General Design Principles Employed In Colorimetric and Fluormentioning

confidence: 99%

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

et al. 2010

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“…[7][8][9][10][11] We are particularly concerned with the understanding and use of structure, conformational aspects and supramolecular interactions to modulate the ability of the receptors to bind different anions. A particularly important class of anion receptors are those based on thiourea [2,[12][13][14][15][16][17][18][19][20][21] functionalities because of their ability to form strong hydrogen-bond complexes with anions, and their synthetic accessibility. Simple bis(thioureas) have been shown to bind glutarate, dihydrogenphosphate and acetate in DMSO [22][23][24][25][26] and have been incorporated into monolayers to mimic ion-channel sensing of hydrophilic anions.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Anion Binding from Unusual Coordination Modes of Bis(thiourea) Ligands in Platinum Group Metal Complexes

Soriano¹,

Lenthall²,

Anderson³

et al. 2010

Chemistry A European J

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Treatment of a range of bis(thiourea) ligands with inert organometallic transition-metal ions gives a number of novel complexes that exhibit unusual ligand binding modes and significantly enhanced anion binding ability. The ruthenium(II) complex [Ru(η(6)-p-cymene)(κS,S',N-L(3)-H)](+) (2b) possesses juxtaposed four- and seven-membered chelate rings and binds anions as both 1:1 and 2:1 host guest complexes. The pyridyl bis(thiourea) complex [Ru(η(6)-p-cymeme)(κS,S',N(py)-L(4))](2+) (4) binds anions in both 1:1 and 1:2 species, whereas the free ligand is ineffective because of intramolecular NH⋅⋅⋅N hydrogen bonding. Novel palladium(II) complexes with nine- and ten-membered chelate rings are also reported.

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“…3A. It has been reported that a strong charge-transfer interaction could occur between this electron-rich aromatic ring (conjugating OH) and electrondeficient amino group [35,36]. Herein, the electron transfer would result in the formation of a Meisenheimer complex between BPA and the primary amino groups on the surface of the AuNCs.…”

Section: Possible Sensing Mechanism Of the Sio 2 @Auncs-mipsmentioning

confidence: 99%

Molecularly imprinted polymers-coated gold nanoclusters for fluorescent detection of bisphenol A

Zhong

et al. 2015

Sensors and Actuators B: Chemical

117

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a b s t r a c tA flexible fluorescent sensing strategy for the recognition and detection of bisphenol A (BPA) has been proposed based on molecularly imprinted polymers (MIPs)-coated gold nanoclusters (AuNCs), by taking advantages of the high selectivity of MIPs and the strong fluorescence property of AuNCs. SiO 2 @AuNCs were initially prepared by making use of the powerful amido bonds between carboxyl-terminated AuNCs and amino-functionalized SiO 2 nanoparticles. Then MIPs-coated AuNCs were formed by anchoring MIP layer on the surface of SiO 2 @AuNCs via a sol-gel process. In the presence of imprinting template BPA, a Meisenheimer complex could be formed between BPA and the primary amino groups on the surface of the AuNCs, and the photoluminescent energy of AuNCs would be transferred to the complex, and thereby result in the fluorescence quenching of AuNCs. The fluorescence-quenching fractions of the sensor presented a satisfactory linearity with BPA concentrations over the range of 0-13.1 M and the detection limit could reach 0.10 M. Distinguished selectivity was also exhibited to BPA over other possibly competing molecules. Moreover, the sensor was successfully applied to determine BPA in seawater, and the average recoveries of BPA at three spiking levels ranged from 91.3 to 96.2% with relative standard deviations below 4.8%. This AuNCs-MIPs based sensor provided great potentials for recognition and determination of phenolic environmental estrogens in complicated samples.

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Dual responsive chemosensors for anions: the combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single molecule

Cited by 224 publications

References 31 publications

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

Enhanced Anion Binding from Unusual Coordination Modes of Bis(thiourea) Ligands in Platinum Group Metal Complexes

Molecularly imprinted polymers-coated gold nanoclusters for fluorescent detection of bisphenol A

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