TD-DFT study on fluoride-sensing mechanism of 2-(2′-phenylureaphenyl)benzoxazole: the way to inhibit the ESIPT process
Literature Information
The fluoride-sensing mechanism of the sensor 2-(2′-phenylurea-phenyl)benzoxazole (PUBO) has been investigated by means of the TD-DFT method. The present theoretical study indicates that there is an excited-state intramolecular proton transfer (ESIPT) process in the sensor PUBO. The added fluoride anion could capture the proton in the free N–H moiety instead of the hydrogen-bonding one. The experimental UV/Vis and fluorescence spectra (J. Org. Chem. 2007, 72, 62) are well reproduced by the calculated vertical excitation energies in the ground state and the first singlet excited state. For example, the calculated emission wavelength of PUBO at 534 nm is very close to the fluorescence band at 554 nm. Furthermore, we theoretically confirmed that the added fluoride anions could inhibit the ESIPT process in PUBO. But different from the classical ESIPT-inhibition mechanism, the ESIPT process in the sensor PUBO is inhibited by the high energy barrier of its deprotonated form rather than by the absence of the transferred proton.
Recommended Journals

Critical Reviews in Solid State and Materials Sciences

Bioorganic & Medicinal Chemistry

Journal of Chemical Sciences

Topics in Catalysis

Journal of Asian Natural Products Research

Journal of the Indian Institute of Science

Acta Metallurgica Sinica-English Letters

NDT & E International

Cellulose

Chinese Journal of Chemistry
Related Literature
A transition-metal-free, base-promoted annulation/ring-cleavage/ring-reconstruction cascade reaction: a facile access to N-protection free indole-indenones
Na Luo, Zhen-Wei Sun, Xing-Xin Xu, Xiao-Qiang Hu, Feng-Cheng Jia
DOI: 10.1039/D1QO01280K
Building of neomycin–nucleobase–amino acid conjugates for the inhibition of oncogenic miRNAs biogenesis
Duc Duy Vo, Cécile Becquart, Thi Phuong Anh Tran, Audrey Di Giorgio, Fabien Darfeuille, Cathy Staedel, Maria Duca
DOI: 10.1039/C8OB01858H
Regioselective synthesis and biological evaluation of N-substituted 2-aminoquinazolin-4-ones
Zhen-Yuan Liao, Wen-Hsiung Yeh, Pen-Yuan Liao, Yu-Ting Liu, Ying-Cheng Chen, Yi-Hung Chen, Tsung-Han Hsieh, Chia-Chi Lin, Ming-Hsuan Lu, Yi-Song Chen, Ming-Chih Hsu, Tsai-Kun Li, Tun-Cheng Chien
DOI: 10.1039/C8OB00624E
Nickel-catalyzed electrochemical reductive relay cross-coupling of alkyl halides with alkyl carboxylic acids
Cong Ma, Dong Liu, Hui Qiu, Bin Cheng, Tian-Sheng Mei
DOI: 10.1039/D1QO01219C
Synthesis and biochemical evaluation of two novel N-hydroxyalkylated cyclosporin A analogs
Viktoria Kahlert, Oliver Ohlenschläger, Jelena Melesina, Christian Lücke
DOI: 10.1039/C8OB00980E
Mixed carboxylic–sulfonic anhydride in reaction with imines: a straightforward route to water-soluble β-lactams via a Staudinger-type reaction
Olga Bakulina, Dmitry Dar'in, Mikhail Krasavin
DOI: 10.1039/C8OB00768C
Insight into the mechanism of the arylation of arenes via norbornene relay palladation through meta- to para-selectivity
Shengnan Liu, Qiong Wang, Fang Huang, Wenjuan Wang, Chong Yang, Jianbiao Liu, Dezhan Chen
DOI: 10.1039/D1QO01500A
Cascade double isocyanide insertion and C–N coupling of 2-iodo-2′-isocyano-1,1′-biphenyls
DOI: 10.1039/C8OB00956B
Novel photoactivatable substrates for Renilla luciferase imaging in vitro and in vivo
Chaochao Zhang, Lin Cheng, Gaopan Dong, Guangxi Han, Xingye Yang, Chunchao Tang, Xiang Li, Yubin Zhou, Lupei Du
DOI: 10.1039/C8OB01192C
You might also like
What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?
(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...
What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?
When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...
Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?
There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...
What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?
1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...
Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?
Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...
What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?
2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...
How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?
Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...
How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?
2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...
What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?
Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...
Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?
In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...
Source Journal
Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.




