Design and application of a fluorescent probe based on ESIPT mechanism for the detection of Cys with o-hydroxyacetophenone structure

2019 ◽  
Vol 11 (19) ◽  
pp. 2513-2517 ◽  
Author(s):  
Cuiyan Han ◽  
Bo Song ◽  
Xin Liang ◽  
Hong Pan ◽  
Wei Dong
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Fluorescent Probe ◽  
Quantitative Measurement ◽  
Cell Imaging ◽  
Intramolecular Proton Transfer ◽  
Design And Application

In this paper, a novel fluorescent probe DHOA based on excited-state intramolecular proton transfer (ESIPT) principle was designed, prepared, and then applied to quantitative measurement and cell imaging of cysteine (Cys).

A water soluble ESIPT-based fluorescent chemodosimeter for the ratiometric detection of palladium ions in aqueous solution and its application in live-cell imaging

2018 ◽  
Vol 42 (19) ◽  
pp. 15587-15592 ◽  
Author(s):  
Jing Huang ◽  
Yu Ding ◽  
Hongyu Fu ◽  
Bo Chen ◽  
Yifeng Han
Keyword(s):  
Aqueous Solution ◽  
Excited State ◽  
Proton Transfer ◽  
Live Cell Imaging ◽  
Cell Imaging ◽  
Intramolecular Proton Transfer ◽  
Live Cell ◽  
Water Soluble ◽  
Ratiometric Detection ◽  
Fluorescent Chemodosimeter

A new Excited State Intramolecular Proton Transfer (ESIPT) based water-soluble fluorescent chemodosimeter for the ratiometric detection of palladium ions has been rationally designed and developed.

scholarly journals A Solvent-Mediated Excited-State Intermolecular Proton Transfer Fluorescent Probe for Fe3+ Sensing and Cell Imaging

Molecules ◽  
2022 ◽  
Vol 27 (2) ◽  
pp. 516
Author(s):  
You Qian ◽  
Fuchun Gong ◽  
Jiguang Li ◽  
Pan Ma ◽  
Hanming Zhu ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Fluorescent Probe ◽  
Cell Imaging ◽  
Cyano Group ◽  
Proton Donor ◽  
Cell Permeability ◽  
One Pot ◽  
Intermolecular Proton Transfer ◽  
Synthesis Strategy

Constructing excited-state intermolecular proton transfer (ESIPT-e) fluorophores represents significant challenges due to the harsh requirement of bearing a proton donor-acceptor (D-A) system and their matching proton donating-accepting ability in the same molecule. Herein, we synthesized a new-type ESIPT-e fluorophor (2-APC) using the “four-component one-pot” reaction. By the installing of a cyano-group on pyridine scaffold, the proton donating ability of -NH2 was greatly enhanced, enabling 2-APC to undergo ESIPT-e process. Surprisingly, 2-APC exhibited dual-emissions in protic solvents ethanol and normal fluorescence in aprotic solvents, which is vastly different from that of conventional ESIPT-a dyes. The ESIPT emission can be obviously suppressed by Fe3+ due to the coordination reaction of Fe3+ with the A-D system in 2-APC. From this basis, a highly sensitive and selective method was established using 2-APC as a fluorescent probe, which offers the sensitive detection of Fe3+ ranging from 0 to 13 μM with the detection limit of 7.5 nM. The recovery study of spiked Fe3+ measured by the probe showed satisfactory results (97.2103.4%) with the reasonable RSD ranging from 3.1 to 3.8%. Moreover, 2-APC can also exhibit aggregation-induced effect in poor solvent or solid-state, eliciting strong red fluorescence. 2-APC was also applied to cell-imaging, exhibiting good cell-permeability, biocompatibility and color rendering. This multi-mode emission of 2-APC is significant departure from that of conventional extended p-conjugated systems and ESIPT dyes based on a flat and rigid molecular design. The “one-pot synthesis” strategy for the construction of ESIPT molecules pioneered a new route to achieve tricolor-emissive fluorophores.

scholarly journals Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents

2018 ◽  
Vol 47 (23) ◽  
pp. 8842-8880 ◽  
Author(s):  
Adam C. Sedgwick ◽  
Luling Wu ◽  
Hai-Hao Han ◽  
Steven D. Bull ◽  
Xiao-Peng He ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Fluorescent Probes ◽  
Environmental Science ◽  
Intramolecular Proton Transfer ◽  
Imaging Agents ◽  
Fluorescence Sensors ◽  
Recent Advances ◽  
Design And Application

We review recent advances in the design and application of excited-state intramolecular proton-transfer (ESIPT) based fluorescent probes. These sensors and imaging agents (probes) are important in biology, physiology, pharmacology, and environmental science.

Molecular Design of Amino-type Hydrogen-Bonding Molecules for Excited-State Intramolecular Proton Transfer (ESIPT)-based Fluorescent Probe using TD-DFT Approach

2021 ◽  
Author(s):  
Narissa Kanlayakan ◽  
Nawee Kungwan
Keyword(s):  
Hydrogen Bonding ◽  
Excited State ◽  
Proton Transfer ◽  
Fluorescent Probe ◽  
Fluorescent Probes ◽  
Molecular Design ◽  
Intramolecular Proton Transfer ◽  
Proton Donor ◽  
Molecular Screening ◽  
Td Dft

A molecular screening for fluorescent probes harnessing excited-stated intramolecular proton transfer (ESIPT) of NH-type molecules having aminophenyl or tosylaminophenyl as a proton donor and benzimidazole, benzoxazole, benzothiazole, or imidazo[1,2-a]pyridine as...

A ratiometric fluorescent probe for magnesium employing excited state intramolecular proton transfer

2008 ◽  
Vol 49 (47) ◽  
pp. 6690-6692 ◽  
Author(s):  
Narinder Singh ◽  
Navneet Kaur ◽  
Ray C. Mulrooney ◽  
John F. Callan
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Fluorescent Probe ◽  
Intramolecular Proton Transfer ◽  
Ratiometric Fluorescent Probe

Aggregation induced enhanced and exclusively highly Stokes shifted emission from an excited state intramolecular proton transfer exhibiting molecule

2017 ◽  
Vol 196 ◽  
pp. 71-90 ◽  
Author(s):  
Santosh Kumar Behera ◽  
Anwesha Murkherjee ◽  
G. Sadhuragiri ◽  
Palani Elumalai ◽  
M. Sathiyendiran ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Cell Imaging ◽  
Inner Filter Effect ◽  
Intramolecular Proton Transfer ◽  
Additional Advantage ◽  
Filter Effect ◽  
Emission Enhancement ◽  
Butyl Phenol ◽  
Tetrahydrofuran Solution

The inner filter effect due to self-quenching dominates the normal emission of dyes at higher concentrations, which would limit their applications. Since normal emission was also observed with aggregation induced emission enhancement (AIEE) active excited state intramolecular proton transfer (ESIPT) exhibiting molecules, two new molecules are synthesized and studied to obtain normal emission free AIEE. The molecules are 4-(3-(benzo[d]thiazol-2-yl)-5-tert-butyl-4-hydroxybenzyl)-2-(benzo[d]thiazol-2-yl)-6-tert-butyl phenol (bis-HPBT) and its oxazole analogue (bis-HPBO). Of these molecules, bis-HPBT, which is weakly fluorescent in tetrahydrofuran solution, shows a sudden high enhancement in fluorescence upon addition of 70% water due to the formation of aggregates. Though the normal emission is also observed in tetrahydrofuran, it is completely eliminated in the aggregates, and the aggregates display exclusive tautomer emission. However, bis-HPBO does not emit such an exclusive tautomer emission in the water/tetrahydrofuran mixture. The enhancement in the fluorescence quantum yield of bis-HPBT in 70% water is ∼300 times higher than that in tetrahydrofuran. The modulated molecular structure of bis-HPBT is the cause of this outstanding AIEE. The observation of almost exclusive tautomer emission is a new additional advantage of AIEE from bis-HPBT over other ESIPT molecules. Since the tautomer emission is highly Stokes shifted, no overlap with the absorption spectrum occurs and therefore, the inner filter effect is averted. The aggregated structure acts as a good fluorescence chemosensor for metal ions as well as anions. The aggregated structure is cell permeable and can be used for cell imaging.

Theoretical study on the sensing mechanism of chalcone-based fluorescence probe for detecting hydrogen sulfide and biothiols

2021 ◽  
Author(s):  
Yunjian Cao ◽  
Lingling Wang ◽  
Ziqi Liu ◽  
Chaofan Sun ◽  
Yuanzuo Li
Keyword(s):  
Hydrogen Sulfide ◽  
Excited State ◽  
Charge Transfer ◽  
Proton Transfer ◽  
Fluorescent Probe ◽  
Theoretical Study ◽  
Fluorescence Probe ◽  
Intramolecular Charge Transfer ◽  
Intramolecular Proton Transfer ◽  
Twisted Intramolecular Charge Transfer

A fluorescent probe 2′-(2,4-dinitro-phenoxy)-4-(dimethylamino) chalcone (Pr1, Spectrochim. Acta, Part A 2021, 244, 118839)based on the twisted intramolecular charge transfer (TICT) and excited state intramolecular proton transfer (ESIPT) was designed and...

scholarly journals Two-photon ESIPT-based fluorescent probe using 4-hydroxyisoindoline-1,3-dione for the detection of peroxynitrite

2021 ◽  
Author(s):  
Luling Wu ◽  
Xue Tian ◽  
Dong Joon Lee ◽  
Juyoung Yoon ◽  
Chang Su Lim ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Fluorescent Probe ◽  
Intramolecular Proton Transfer ◽  
Two Photon ◽  
Photon Excitation ◽  
Two Photon Excitation

Excited-state intramolecular proton transfer (ESIPT)-based fluorophores with two-photon excitation fluorescence (TPEF) are rare. Our aim with this research was to develop ESITP-based fluorophores exhibiting TPEF. Herein, we used 4-hydroxyisoindoline-1,3-dione as...

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