The effects of electron-withdrawing and electron-donating groups on the photophysical properties and ESIPT of salicylideneaniline

Li-feng, Jia; Liu, Yufang

doi:10.1016/j.saa.2020.118719

Cited by 23 publications

(5 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The influence of these factors on ESIPT behavior has been discussed [23][24][25][26][27][28][29][30][31][32]. In recent years, many researchers have studied the effects of various substituents (such as -NO 2 , -COOH, or -CN) on the proton transfer process [33][34][35][36][37][38]. For example, the substituent effects on the photophysical properties and ESIPT process of the Schiff base derivatives were investigated by Li et al [33].…”

Section: Introductionmentioning

confidence: 99%

Substituent effect on photophysical properties and proton transfer process of HBQ derivatives

Song

Wang

Pan

2023

J Chinese Chemical Soc

View full text Add to dashboard Cite

BackgroundIn view of the potential applications of 10‐hydroxybenzo [h] quinoline (HBQ) in biological probes and organic light‐emission devices, the excited state intramolecular proton transfer (ESIPT) mechanism of HBQ was investigated theoretically in the work.AimsIn order to give a detailed reaction mechanism, the ESIPT of molecular system with hydrogen bond is systematically studied using density functional theory and density functional theoryMethodsUsing density functional theory (DFT) and time‐dependent density functional theory (TDDFT), we investigate the photophysical properties and excited state proton transfer of 10‐hydroxybenzo [h] quinoline (HBQ)derivatives.ResultsThe optimized structure shows that HBQ1 and HBQ2 have no stable structure in S1 state. The analysis of bond length parameters and infrared vibration spectroscopy proved that the substituent groups regulated the hydrogen bond strength in the S0 state.ConclusionTherefore, substitution position will affect the excited state intramolecular proton transfer and the photophysical properties of the molecule.

show abstract

Section: Introductionmentioning

confidence: 99%

Substituent effect on photophysical properties and proton transfer process of HBQ derivatives

Song

Wang

Pan

2023

J Chinese Chemical Soc

View full text Add to dashboard Cite

show abstract

“…Many great efforts have been made to investigate the influence of numerous factors, including the type of substituent, solvent polarity, and hydrogen bonding strength, on ESIPT processes. [8][9][10][11][12][13][14][15][16][17][18][19] For example, Guo et al studied the effects of substituent groups on proton donor fragments, including À H, À CH 3 , À F, À Cl, À Br, À OCH 3 , and À NH 2 , on the intramolecular hydrogen bonding and energy barrier in the ESIPT process of methyl 5-R-salicylates derivatives by computational chemistry methods. [20 ] Their results demonstrated that the À H atom results in a stronger intramolecular hydrogen bond interaction and a lower energy barrier of proton transfer reaction compared to other substituents, while À NH 2 induced the highest energy barrier among all substituents.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Molecular Principles of the Excited‐State Intramolecular Thiol Proton Transfers in 3‐thiolflavone Derivatives

Sun

Kripalani

Chi

2023

Chemistry An Asian Journal

View full text Add to dashboard Cite

The excited‐state intramolecular proton transfer (ESIPT) effect has attracted considerable attention due to its potential applications in photoluminescent materials. However, only a few theoretical reports have investigated the ESIPT process involving sulfur‐hydrogen bonds. Herein, we systematically investigated the ESIPT effect of three 3‐thiolflavone derivatives containing sulfur‐hydrogen bonds with M06‐2X functional combined Def2‐TZVP basis set. The intramolecular sulfur‐hydrogen bonds were confirmed in the ground and excited states via analyzing the bond lengths, interaction energies, and infrared vibrational spectra. Besides, we demonstrated that the electron‐withdrawing group led to a more stable tautomer compared to the electron‐donating group. Conversely, the electron‐donating group played a crucial role in reducing the energy barrier of the ESIPT reaction due to the strengthening of the hydrogen bond in the excited state. Interestingly, the substituent group can determine the excited‐state electronic properties of keto tautomers. Specifically, the electron‐withdrawing group caused significant improvement in the nπ* transition configuration, significantly reducing the radiation rate. The electron‐donating group increased the proportion of the ππ* transition configuration, thus, the keto tautomer had bright emission. We expect these findings to open new avenues for designing potential luminescent materials.

show abstract

“…The substitution of functional groups may provide an effective way to fine-tune the ESIPT process and photophysical properties of compounds. [23][24][25][26] According to the previous reports, Ma et al [27] studied the substituent effect on ESIPT process of 1-(aclamino)-anhraquinones. Takagi et al [28] probed the ESIPT fluorescence properties of methoxysubstituted 2-hydroxyphenylbenzimidazole.…”

Section: Introductionmentioning

confidence: 99%

A DFT/TD-DFT study of effect of different substituent on ESIPT fluorescence features of 2-(2′-hydroxyphenyl)-4-chloromethylthiazole derivatives

Su¹,

Liang²,

Fang³

2022

Chinese Phys. B

View full text Add to dashboard Cite

Based on density functional theory (DFT) and time-dependent density functional theory (TD-DFT), the effects of substituent on the excited-state intramolecular proton transfer (ESIPT) process and photophysical properties of 2-(2′-hydroxyphenyl)-4-chloromethylthiazole (HCT) are studied. The electron-donating group (CH3, OH) and electron-withdrawing group (CF3, CHO) are introduced to analyze the changes of intramolecular H-bond, the frontier molecular orbitals, the absorption/fluorescence spectra, and the energy barrier of ESIPT process. The calculation results indicate that electron-donating group strengthens the intramolecular H-bond in the S1 state, and leads to an easier ESIPT process. The electron-withdrawing group weakens the corresponding H-bond and makes ESIPT process a little harder. Different substituents also affect the photophysical properties of HCT. The electron-withdrawing group (CF3, CHO) has a little effect on electronic spectra. The electron-donating group (CH3, OH) red-shifts both the absorption and fluorescence emission peaks of HCT, respectively, which causes the Stokes shift to increase.

show abstract

The effects of electron-withdrawing and electron-donating groups on the photophysical properties and ESIPT of salicylideneaniline

Cited by 23 publications

References 41 publications

Substituent effect on photophysical properties and proton transfer process of HBQ derivatives

Substituent effect on photophysical properties and proton transfer process of HBQ derivatives

Molecular Principles of the Excited‐State Intramolecular Thiol Proton Transfers in 3‐thiolflavone Derivatives

A DFT/TD-DFT study of effect of different substituent on ESIPT fluorescence features of 2-(2′-hydroxyphenyl)-4-chloromethylthiazole derivatives

Contact Info

Product

Resources

About