Highly sensitive fluorescent sensing for water based on poly(m-aminobenzoic acid)

Deng, Qiling; Li, Yanli; Wu, Jianhua; Liu, Yang; Fang, Guozhen; Wang, Shuo; Zhang, Yukui

doi:10.1039/c2cc17856g

Cited by 124 publications

(54 citation statements)

References 21 publications

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“…This method of water detection is the most sensitive compared with water detection methods reported in the literature. [1][2][3][4][5][6][7] …”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3] Recently, Deng et al reported a poly (m-aminobenzoic acid)-based water sensor that is highly efficient. [4] In another example, it was demonstrated that the watersoluble poly(phenylene ethynylene) undergoes aggregation and fluorescence quenching in water. [5] Harima et al have developed a fluorescence sensor for detection of water in organic solvents based on photo-induced electron transfer (PET) of amino acid-coupled anthracene.…”

Section: Introductionmentioning

confidence: 99%

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Detection of Trace Amounts of Water in Organic Solvent by 8-Hydroxypyrene-1,3,6-Trisulfonic Acid Trisodium Salt

et al. 2014

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A colorimetric and fluorescent sensor was developed based on 8-hydroxy-1,3,6-pyrenetrisulfonic acid trisodium salt (HPTS) for the detection of trace amounts of water in polar organic solvents. Fluorescence and UV-visible absorption spectra of HPTS were measured in a variety of organic solvents (DMF, DMSO, ethanol, methanol). Fluorescence maxima comparable with maximum/minimum ratios were determined by using UV-visible absorption spectroscopy. The HPTS sensor exhibits high sensitivity for water with a detection limit as low as 0.0001 to 0.0005 wt-%. In addition, naked-eye inspection of solutions of HPTS sensor in organic solvents before and after addition of water showed dramatic changes in colour from blue to green. These findings can be applied in the use of HPTS as a molecular probe for trace amounts of water in organic solvents.

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“…This method of water detection is the most sensitive compared with water detection methods reported in the literature. [1][2][3][4][5][6][7] …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Detection of Trace Amounts of Water in Organic Solvent by 8-Hydroxypyrene-1,3,6-Trisulfonic Acid Trisodium Salt

et al. 2014

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“…The 1 H NMR (600 MHz) and 13 C NMR (150 MHz) spectra were measured on a Varian VNS spectrometer and referenced to the residual solvent signals. UVevis spectra were recorded with a Shinco S-3100 spectrophotometer.…”

Section: Generalmentioning

confidence: 99%

“…In fact, fluorescent sensors for the sensitive sensing of the water content in organic solvents have been successfully designed using various fluorophores of 1,8-naphthalimide [7,8], flavone derivatives [9], 8-hydroxyquinolines [10], 2,3-biphenyl quinoxaline 6-amine [11], and thioxanthone fluorophores [12]. The development of sensors based on fluorescent conjugated poly(m-aminobenzoic acid) [13], europium ternary complexes immobilized on glass surfaces [14], and acridine orange-based optical fiber [15] is also noteworthy. On the other hand, colorimetric sensors based on merocyanine dyes, such as various isomers of 4-[(4 0 -oxocyclohexa-2 0 ,5 0 -dienylidene)ethylidene]-1,4-dihydropyridine [16,17] and hydroxycoumarin derived dyes [18], and using their unique solvatochromism have been reported.…”

Section: Introductionmentioning

confidence: 99%

Signaling of water content in organic solvents by solvatochromism of a hydroxynaphthalimide-based merocyanine dye

Park

Chang

2015

Dyes and Pigments

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“…[1][2][3][4][5][6][7][8][9][10][11] In most of these fluorescence water sensors developed so far, the fluorescence intensity decreases as the amount of water increases in organic solvents and this feature can be attributed to the aggregation of sensors or the formation of 30 hydrogen bonding between sensor and water molecules with the increase in the water content. [1][2][3][4][5][6][7] However, this fluorescence quenching system makes it difficult to detect trace amounts of water. Additionally, the detection and quantification of water based on the fluorescence quenching system depend strongly on 35 the kind of solvents (polar, less polar, protic and aprotic solvents).…”

Section: Introductionmentioning

confidence: 99%

Molecular design and synthesis of fluorescence PET (photo-induced electron transfer) sensors for detection of water in organic solvents

et al. 2013

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A series of anthracene-boronic acid ester OM-1, OM-2, OU-1, and OU-2 have been designed and synthesized as a new class of fluorescence PET (photo-induced electron transfer) sensors for detection and quantification of a trace amount of water in organic solvents. OM-1 and OM-2 have a boronic acid ester and bisboronic acid ester, respectively, located at the proximity of a tertiary amino group as an electron donor via a methylene spacer at the 9-position on the anthracene fluorophore. In OU-1, on the 10 other hand, a boronic acid ester is directly connected to the 10-position on the anthracene fluorophore. OU-2 has bisboronic acid ester, which are located at the same positions as those of OM-1 and OU-1. It was found that OM-1 and OM-2 show enhancement of fluorescence with the increase in water content for various solvents (polar, less polar, protic and aprotic solvents), which can be attributed to the suppression of PET due to the formation of fluorescent ionic structure OM-1a or OM-2a by hydrolysis. 15For OU-1 and OU-2, on the other hand, there is no appreciable change in fluorescence intensity upon addition of water to the solution. We propose that a key point for creating a highly-sensitive fluorescence PET sensor for detection of a trace amount of water is to design molecular structures capable of forming stable fluorescent ionic structure between the protonated tertiary amino group and the hydroxylated boronic acid ester by hydrolysis. 20 65 range of application to various solvents, we have designed and synthesized anthracene-boronic acid ester OU-1 and anthracenebisboronic acid ester OU-2 (Scheme 3). In OU-1, a boronic acid ester is directly connected to the 10-position on the anthracene fluorophore. On the other hand, OU-2 has bisboronic acid ester, 70 which are located at the same positions as those of OM-1 and OU-1. This work indicates that a key point for creating a highly-Journal Name, [year], [vol], 00-00 | 5 5 10 15 20 25 Fig. 6 Fluorescence peak intensity of OM-2 at around 415 nm (λ ex = 366 nm) as a function of water content in (a) 1,4-dioxane, (b) THF, (c) acetonitrile and (d) ethanol.

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Highly sensitive fluorescent sensing for water based on poly(m-aminobenzoic acid)

Cited by 124 publications

References 21 publications

Detection of Trace Amounts of Water in Organic Solvent by 8-Hydroxypyrene-1,3,6-Trisulfonic Acid Trisodium Salt

Detection of Trace Amounts of Water in Organic Solvent by 8-Hydroxypyrene-1,3,6-Trisulfonic Acid Trisodium Salt

Signaling of water content in organic solvents by solvatochromism of a hydroxynaphthalimide-based merocyanine dye

Molecular design and synthesis of fluorescence PET (photo-induced electron transfer) sensors for detection of water in organic solvents

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