Ratiometric fluorescent monitoring of methanol in biodiesel by using an ESIPT-based flavonoid probe

Qin, Tianyi; Liu, Bin; Huang, Yingying; Yang, Kuan; Zhu, Kangning; Luo, Zijie; Pan, Chengjun; Wang, Lei

doi:10.1016/j.snb.2018.09.056

Cited by 40 publications

(12 citation statements)

References 37 publications

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“…This detection limit was found to be comparable with other traditional methods, such as voltammetry (0.02%), electrochemistry (0.03%), and nearinfrared spectroscopy (0.023%). 31 The energy-minimized structure of 1 (at gas phase) indicates a puckered geometry with a dihedral angle of ∼57°(between the pyrene unit and central aryl ring of the terpyridine moiety). However, the excited-state geometry showed a comparatively less distorted structure as the dihedral angle reduced from ∼57 to ∼33°.…”

Section: ■ Results and Discussionmentioning

confidence: 98%

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Hydrogen Bonding-Induced Unique Charge-Transfer Emission from Multichromophoric Polypyridyl Ligands: Ratiometric Probing of Methanol Impurity in Commercial Biofuels

Dey

Bhattacharya

2021

ACS Sustainable Chem. Eng.

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This work is focused on utilizing fluorescent molecules for sensing the methanol content in (bio)fuels. Multichromophoric polypyridyl ligands with pyrene (1) and anthracene (2) as aryl residues have been synthesized. The twisted geometry of the probe molecules in both the solid state and aprotic solvents significantly curtails the electronic communication between the aryl moiety and pyridyl ligand (terpyridine). However, the excited-state hydrogen bonding interactions of methanol with terpyridine nitrogens result in the formation of a nearly planar conformation with larger charge separation. Thus, a broad “structureless” fluorescence spectrum was observed specifically in methanol with an exceptionally large Stokes shift (detection limit: 0.13%). However, the extent of redshift was found to be attributed to the angle of twisting as well as the electronic nature of the aryl moiety. Considering its high sensitivity, probe 1 is utilized for the detection of methanol impurity in soy-based biodiesel samples, like B100, B20, and so on. Interference studies indicate that the presence of competitive byproducts, such as monoglycerides and diglycerides, or unconsumed starting materials, such as fatty acid methyl esters poses no serious threats in methanol detection. Finally, the methanol-specific fluorescence response has been utilized to design paper strips for on-location detection of methanol contamination in biofuel samples.

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Section: ■ Results and Discussionmentioning

confidence: 98%

“…The blank variation method indicates that one can detect as low as 0.13% v/v of methanol in biodiesel samples using compound 1 . This detection limit was found to be comparable with other traditional methods, such as voltammetry (0.02%), electrochemistry (0.03%), and near-infrared spectroscopy (0.023%) …”

Section: Resultsmentioning

confidence: 99%

Hydrogen Bonding-Induced Unique Charge-Transfer Emission from Multichromophoric Polypyridyl Ligands: Ratiometric Probing of Methanol Impurity in Commercial Biofuels

Dey

Bhattacharya

2021

ACS Sustainable Chem. Eng.

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“…Industrial alcohol contains about 4% of methanol. Taking advantage of industrial alcohol to produce shoddy edible wine in a fake way presumably may cause methanol poisoning. , Besides, methanol vapors can also injure the nervous tissue and connective tissue of mammals. , Hence, rapid, accurate, and effective detection of methanol and its vapor is tremendously significant and necessary for ensuring food safety, maintaining public social safety, and protecting human health. − Various methods for detection of methanol and its vapor have been exploited, such as high-performance liquid and gas chromatography; infrared (IR), H 1 NMR, electrochemical, enzymatic techniques; gas sensors, and so forth. − However, high cost, inconvenience, and special equipment obstruct the application of these methods in actual sensing. Therefore, it is imperative to procure a rapid, less-consumed, and easy-to-use method to identify and respond to methanol or its vapor.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly of Lanthanide-Based Metallogel Nanoplates into Microcubic Blocks as Self-Calibrating Luminescent Methanol Sensors

Yang

Liu

Zhong

et al. 2021

ACS Appl. Nano Mater.

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Because of the serious physiological toxicity of methanol, detection of methanol in ethanol medium is tremendously significant. Herein, excellent luminescent lanthanide-based supramolecular metallogels were prepared with the conventional low-molecular-weight-gelator 1,3,5-benzenetricarboxylic acid (BTC) and the lanthanide trivalent cations (Tb 3+ and Eu 3+ ), which exhibit distinctive characteristic photoluminescent emission of lanthanides. These metallogels were synthesized depending on the one-step method of a high-concentration reaction synergized with heat-assisted ultrasound. The mechanical characteristics of the supramolecular metallogels were investigated through a rheological study. The scanning electron microscopy study revealed the supramolecular interconnection structure of microcubic blocks formed through irregular self-assembly of nanoplates. The bi-metallogel (Eu/Tb-G) with an obvious brilliant yellow emission signal was favorably fabricated via utilizing the lanthanide co-doping strategy and manifests the characteristic emission bands of lanthanide trivalent ions (Eu 3+ and Tb 3+ ) simultaneously. The energy-transfer behavior between Tb 3+ and Eu 3+ was systematically studied. What is striking is that methanol facilitates the increase of Tb 3+ fluorescence intensity without affecting the characteristic emission of Eu 3+ , and this phenomenon induces a unique emission proportion between Tb 3+ and Eu 3+ ions. Inspired by this, a self-calibrated fluorescence sensor of methanol is acquired, which adopts the dynamic emission of Tb 3+ that can vary continuously and regularly as the target identification detection signal and utilizes the static emission of Eu 3+ as the internal reference system. The change of fluorescence lifetime and quantum yield confirmed that this obvious visual optical color signal varying phenomenon can be ascribed to the internal energy-transfer process conversion caused by the unique host−quest interaction between methanol and Eu/Tb-G. In addition, the prepared Eu/Tb-G paper-based sensor has good stimulation response and recyclability to methanol vapor. The above discussion can establish Eu/Tb-G as a ratiometric and colorimetric fluorescent sensor for the detection of methanol and its vapor.

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“…[13][14][15] Thus, using a reaction based chemical sensor, MeOH detection in commercial alcoholic beverages and hand sanitizers containing a large amount of EtOH/ i PrOH as well as water is an extremely challenging task. [16][17][18] In the search for an alternative method of detection, researchers focused on various other analytical procedures, such as different types of mass spectrometry (MS), [19][20][21] gas chromatography, [22][23][24] cyclic voltammetry, 25 capillary electrophoresis, 26 quartz crystal microbalances (QCMs) and so on. 27 However, costly sophisticated instrumentation, the requirement of skilled technicians or tedious standardizations for the previous methods are major disadvantages for using them in routine analysis.…”

Section: Introductionmentioning

confidence: 99%

Fluorometric trace methanol detection in ethanol and isopropanol in a water medium for application in alcoholic beverages and hand sanitizers

Roy

Das²,

Ray³

et al. 2021

RSC Adv.

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Ratiometric fluorescent monitoring of methanol in biodiesel by using an ESIPT-based flavonoid probe

Cited by 40 publications

References 37 publications

Hydrogen Bonding-Induced Unique Charge-Transfer Emission from Multichromophoric Polypyridyl Ligands: Ratiometric Probing of Methanol Impurity in Commercial Biofuels

Hydrogen Bonding-Induced Unique Charge-Transfer Emission from Multichromophoric Polypyridyl Ligands: Ratiometric Probing of Methanol Impurity in Commercial Biofuels

Self-Assembly of Lanthanide-Based Metallogel Nanoplates into Microcubic Blocks as Self-Calibrating Luminescent Methanol Sensors

Fluorometric trace methanol detection in ethanol and isopropanol in a water medium for application in alcoholic beverages and hand sanitizers

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