An ESIPT-based fluorescent probe for the detection of phosgene in the solution and gas phases

Wu, Cuiyan; Xu, Hai; Li, Yaqian; Xie, Rui-Hua; Li, Peijuan; Pang, Xiao; Zhou, Zile; Gu, Biao; Li, Haitao; Zhang, Youyu

doi:10.1016/j.talanta.2019.03.003

Cited by 53 publications

(20 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Naturally, molecules showing TICT fluorescence do not always produce dual fluorescence; there have recently been an increasing number of literature reports discussing this type of processes and systems leading to non-radiative deactivation of the excited state. Moreover, the molecules may also show the presence of multi-stage phototautomerization processes, ESIPT (excited state intramolecular proton transfer) [ 32 , 33 , 34 , 35 , 36 ]. The properties characterizing ESIPT molecules include dual fluorescence emission, a relatively significant Stokes shift, exceptional process dynamics, as well as high sensitivity of emission spectra to changing properties of the medium [ 37 , 38 , 39 , 40 ].…”

Section: Introductionmentioning

confidence: 99%

ESIPT-Related Origin of Dual Fluorescence in the Selected Model 1,3,4-Thiadiazole Derivatives

et al. 2020

View full text Add to dashboard Cite

In our previous work, we discussed the emergence of the dual fluorescence phenomenon in selected compounds from the group of 1,3,4-thiadiazoles. The results obtained in a number of experimental studies, supported by [TD]DFT calculations, clearly indicated that the phenomenon of dual fluorescence stemmed from an overlap of several factors, including the correct conformation of the analyzed molecule and, very significantly in this context, aggregation effects. Where those two conditions were met, we could observe the phenomenon of intermolecular charge transfer (CT) and the emergence of electronic states responsible for long wave emissions. However, in light of the new studies presented in this paper, we were able, for the first time, to provide a specific theory for the effect of dual fluorescence observed in the analyzed group of 1,3,4-thiadiazoles. We present the results of spectroscopic measurements conducted for two selected analogues from the 1,3,4-thiadiazole group, both in polar and non-polar solvents, which clearly evidence (as we have already suspected in the past, albeit have not shown in publications to date) the possibility of processes related to emission from the tautomer formed in the process of excited state intramolecular proton transfer, which is responsible for the long-wavelength emissions observed in the selected analogues. The presented results obtained with the use of UV-Vis, fluorescence (stationary and time-resolved), FTIR, and Raman spectroscopy, as well as from calculations of dipole moment changes between the ground and excited state with the use of two derivatives with different structures of the resorcylic system, corroborated our standing hypothesis. At the same time, they excluded the presence of ground state keto forms of the analyzed analogues unless necessitated by the structure of the molecule itself. In this case, aggregation factors enhance the observed effects related to the dual fluorescence of the analyzed compounds (by way of AIE—aggregated induced emissions).

show abstract

Section: Introductionmentioning

confidence: 99%

ESIPT-Related Origin of Dual Fluorescence in the Selected Model 1,3,4-Thiadiazole Derivatives

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Photophysical and NMR studies suggested the complexation of AcO – with P43 . Phenanthro[9,10- d ]imidazole P65 was applied by Wu et al as a phosgene ( 130 ) sensor based on the ESIPT process . Phosgene, is a highly reactive and colorless gas, widely used in the production of isocyanates, pesticides, dyes, pharmaceuticals, and other materials. , The chemical is considered highly toxic with an odor-recognition threshold (1.0 ppm) that exceeds the 24-h-exposure safety margin of ∼0.6 ppb. , The green emission of compound P65 at 469 nm was diminished upon the addition of triphosgene/tetraethylammonium (TEA), which generates phosgene; this was associated with a progressive fluorescence emission at 393 nm (bluish-violet) (Figure a).…”

Section: Fluorescent Imidazole Sensor Based On Esipt Processmentioning

confidence: 99%

“…(1) Acetyl chloride, (2) p -toluene sulfonyl chloride, (3) thionyl chloride, (4) phosphorus oxychloride, (5) oxalyl chloride, (6) triphosgene, and (7) phosgene (0.5 ppm). Adapted with permission from ref . Copyright 2019 Elsevier.…”

Section: Fluorescent Imidazole Sensor Based On Esipt Processmentioning

confidence: 99%

Aryl-Phenanthro[9,10-d]imidazole: A Versatile Scaffold for the Design of Optical-Based Sensors

et al. 2022

View full text Add to dashboard Cite

Fluorescent and colorimetric sensors are important tools for investigating the chemical compositions of different matrices, including foods, environmental samples, and water. The high sensitivity, low interference, and low detection limits of these sensors have inspired scientists to investigate this class of sensing molecules for ion and molecule detection. Several examples of fluorescent and colorimetric sensors have been described in the literature; this Review focuses particularly on phenanthro [9,10d]imidazoles. Different strategies have been developed for obtaining phenanthro [9,10d]imidazoles, which enable modification of their optical properties upon interaction with specific analytes. These sensing responses usually involve changes in the fluorescence intensity and/or color arising from processes like photoinduced electron transfer, intramolecular charge transfer, intramolecular proton transfer in the excited state, and Forster resonance energy transfer. In this Review, we categorized these sensors into two different groups: those bearing formyl groups and their derivatives and those based on other molecular groups. The different optical responses of phenanthro [9,10-d]imidazole-based sensors upon interaction with specific analytes are discussed.

show abstract

“…2-(2-aminophenyl)benzothiazole (ABT) reported by Chen et al in 2017 35 and 2-(1 H -phenanthro[9,10- d ]imidazol-2-yl)phenol (Pi) reported by Wu et al in 2019. 36 Despite successful application of the two ESIPT based probes, ABT is unable to discriminate between phosgene and triphosgene, and Pi suffers from high LoD in solution (0.14 μM).…”

Section: Introductionmentioning

confidence: 99%

An amino-substituted 2-(2′-hydroxyphenyl)benzimidazole for the fluorescent detection of phosgene based on an ESIPT mechanism

Zhang

et al. 2021

RSC Adv.

View full text Add to dashboard Cite

show abstract

An ESIPT-based fluorescent probe for the detection of phosgene in the solution and gas phases

Cited by 53 publications

References 26 publications

ESIPT-Related Origin of Dual Fluorescence in the Selected Model 1,3,4-Thiadiazole Derivatives

ESIPT-Related Origin of Dual Fluorescence in the Selected Model 1,3,4-Thiadiazole Derivatives

Aryl-Phenanthro[9,10-d]imidazole: A Versatile Scaffold for the Design of Optical-Based Sensors

An amino-substituted 2-(2′-hydroxyphenyl)benzimidazole for the fluorescent detection of phosgene based on an ESIPT mechanism

Contact Info

Product

Resources

About