Revealing the ESIPT process in benzoxazole fluorophores within polymeric matrices through theory and experiment DOI
Luís Gustavo Teixeira Alves Duarte, Emmanuel Santos Moraes, Priscila Sayoko Silva Wakabayashi

et al.

Photochemistry and Photobiology, Journal Year: 2024, Volume and Issue: unknown

Published: June 26, 2024

Abstract The impact of the polymeric matrix on photophysical characteristics monomeric dyes responsive to excited‐state intramolecular proton transfer (ESIPT) was investigated through UV–Vis absorption as well steady‐state and time‐resolved emission spectroscopies. For this purpose, two benzoxazole monomers (M1 M2) with acryloyl groups at different positions in their molecular structures were employed facilitate covalent bonding within a styrene chain. Our findings reveal significant variations properties due proximity groups, which affects energy barrier ESIPT reaction, wavelength, balance between normal tautomeric forms. experimental results corroborated theoretical investigations DFT/TDDFT level, specifically using B3LYP‐D3/def2‐TZVP methodology. Three notable observations emerged: donor/acceptor meta/para induced electron distribution changes, causing red‐shifted for M2; polymer film, particularly PM1, hydrogen bond deactivation favored N* over T* emission; zwitterionic character species. This study underscores advantages functionalization polymers, can lead colorless films prevalent or emission, contributes valuable insights into design strategies tailoring materials.

Language: Английский

Conjugated Iminodibenzyl Dyes Incorporating Phenolic Hydroxyl Group and Strong Electron Donating or Accepting Groups for Facilitating ESIPT and Proton Transfer in Six- or Seven-Membered Cycles DOI

Xiaozhuan Qin,

Hongru Li, Yufei Wang

et al.

Journal of Fluorescence, Journal Year: 2025, Volume and Issue: unknown

Published: April 10, 2025

Language: Английский

Citations

2
Advances in Organic Fluorescent Probes for Intracellular Zn2+ Detection and Bioimaging DOI Creative Commons
Yi Chen

Molecules, Journal Year: 2024, Volume and Issue: 29(11), P. 2542 - 2542

Published: May 28, 2024

Zinc ions (Zn2+) play a key role in maintaining and regulating protein structures functions. To better understand the intracellular Zn2+ homeostasis signaling role, various fluorescent sensors have been developed that allow monitoring of concentrations bioimaging live cells real time. This review highlights recent development organic probes for detection imaging Zn2+, including design construction probes, response mechanisms, their applications to on-site. Finally, current challenges prospects are discussed.

Language: Английский

Citations

9
AI‐Powered Mining of Highly Customized and Superior ESIPT‐Based Fluorescent Probes DOI Creative Commons

Wenzhi Huang,

Shuai Huang,

Yanpeng Fang

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: unknown

Published: July 17, 2024

Abstract Excited‐state intramolecular proton transfer (ESIPT) has attracted great attention in fluorescent sensors and luminescent materials due to its unique photobiological photochemical features. However, the current structures are far from meeting specific demands for ESIPT molecules different scenarios; try‐and‐error development method is labor‐intensive costly. Therefore, it imperative devise novel approaches exploration of promising fluorophores. This research proposes an artificial intelligence approach aiming at exploring efficiently. The first high‐quality dataset a multi‐level prediction system constructed that realized accurate identification large number compounds under stepwise distinguishing conventional then molecules. Furthermore, key structural features contributed revealed by using SHapley Additive exPlanations (SHAP) method. Then three strategies proposed ensure process while keeping good safety, pharmacokinetic properties, structures. With these strategies, >700 previously unreported screened pool 570 000 compounds. biosafety optimal successfully validated quantitative calculation experiment. expected bring new paradigm ideal

Language: Английский

Citations

9
Multi-color long persistent luminescence in metal-organic frameworks regulated by dual channels of distorted second building units and organic ligand and applied in printing, message encryption and writing DOI
Zheng Wang, Junjie Pan,

Xin‐Qi Chen

et al.

Chemical Engineering Journal, Journal Year: 2025, Volume and Issue: unknown, P. 161076 - 161076

Published: Feb. 1, 2025

Language: Английский

Citations

1
Molecular Switches Guided by a Reversible Access to Room-Temperature Phosphorescence and ESIPT Fluorescence DOI
Vyacheslav E. Olennikov, В. В. Зверева, В. В. Кривенцов

et al.

Inorganic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 2, 2025

This work contributes to luminescent molecular switches featuring several emission pathways, which can be activated by external stimuli. We designed Zn complexes with phenylbenzothiazole-based α-aminomethylphosphine oxide (L) and isolated them as crystalline phases, α-[ZnL2Cl2], [ZnL(EtOAc)Cl2], [ZnL2Cl2]·1.5CH2Cl2, [ZnL2Cl2]·1.5CHCl3. They feature an intramolecular hydrogen bond of medium strength, capable excited-state proton transfer (ESIPT), well able for intersystem crossing between singlet triplet states. Since neither these processes is predominant, one or the other occur depending on a slight change in geometry. The phases reveal red-colored ESIPT fluorescence, while metastable amorphous phase β-[ZnL2Cl2] similar structure coordination center reveals yellow-colored room-temperature phosphorescence. Combined experimental quantum-chemical TD-DFT study clarified dual behavior polymorphs α-[ZnL2Cl2] β-[ZnL2Cl2], attributed high dependence probability geometry phenylbenzothiazole moiety. reversible transition, accompanied mechanism (ESIPT fluorescence vs phosphorescence), manipulated fuming CHCl3 Et2O, respectively. have demonstrated good adhesive properties polymer-free film toward glass plastic, naked-eye color response easy recovery CHCl3.

Language: Английский

Citations

1
Ground-State Tautomerism and Excited-State Proton Transfer in 7-Hydroxy-4-methyl-8-((phenylimino)methyl)-2H-chromen-2-one as a Potential Proton Crane DOI Creative Commons
Daniela Antonová, Liudmil Antonov

Physchem, Journal Year: 2024, Volume and Issue: 4(1), P. 91 - 105

Published: March 11, 2024

The tautomerism in the title compound as a potential long-range proton transfer (PT) switch has been studied by using DFT and TD-DFT approaches. data show that aprotic solvents, enol tautomer dominates, while increase content of keto (short-range PT) rises function polarity solvent. In ethanol, due to specific solute–solvent stabilization through intermolecular hydrogen bonding, substantial amount forms exists solution. irradiation leads two competitive processes excited state, namely ESIPT trans/cis isomerization around azomethine bond other structurally similar Schiff bases. is not suitable for bistable tautomeric switching, where PT occurs, difficult enolization coumarin carbonyl group.

Language: Английский

Citations

6
Assessment of the Microbiological Potential and Spectroscopic Properties of New Imino-1,3,4-Thiadiazoles Showing the ESIPT Effect Strongly Enhanced by Aggregation DOI Creative Commons

Edyta Chruściel,

Lidia Ślusarczyk, Bożena Gładyszewska

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(3), P. 531 - 531

Published: Jan. 24, 2025

There is currently a growing interest in imino derivatives of compounds such as thiadiazoles and other groups whose extended π-electron systems enhance their photophysical properties. These also show low toxicity strong antifungal activity, making them effective against fungal pathogens crops. For the above reasons, first part paper, structure selected analogs was considered, detailed spectroscopic analyses were conducted focusing on excited state intramolecular proton transfer (ESIPT) process taking place same. Measurements taken terms absorption spectroscopy electron fluorescence, synchronous spectra, fluorescence lifetimes, well calculations quantum efficiency solvents concentrations. In spectral observations, ESIPT manifested several very distinct dual fluorescence. Moreover, molecules, this phenomenon strongly related to molecular aggregation, which associated with not efficient but nonetheless visible AIE (Aggregation-Induced Emission) type. second preliminary study presented exploring microbiological properties imino-1,3,4-thiadiazole context potential applicability inhibitors affecting development growth some most important attacking cereal crops posing an increasing threat modern agriculture. Overall, research article provides detailed, experimental analysis imino-thiadiazoles points use novel solutions capable limiting cereals.

Language: Английский

Citations

0
A Phototautomeric 3D Covalent Organic Framework for Ratiometric Fluorescence Humidity Sensing DOI

Xuan Yao,

Zhang Youchang, Yu Qiu

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 6, 2025

Photoinduced proton transfer is an essential photochemical process for designing photocatalysts, white light emitters, bioimaging, and fluorescence sensing materials. However, deliberate control of the excited/ground states meticulous manipulation excited state intramolecular (ESIPT) pathway constitute a significant challenge in liquids dense solids. Here, we present integration hydronaphthoquinone fluorophore into crystalline, porous, phototautomeric dynamic 3D covalent organic framework (COF) to show guest-induced turn-on, emission redshift enhancement, shortened lifetimes ratiometric humidity sensing. Theoretical spectroscopic studies provide mechanistic insights conformational dynamics, charge coupled with local excitation, ground-state uphill regulation multiple tautomers. We illustrate sensitive, rapid, steady, self-calibrated wide range benefiting from architectural chemical robustness crystallinity such COF. These findings molecular design functional porous materials that integrate host-guest mutual recognition photoelectronic response multiplex environmental monitoring biomedical diagnostics applications.

Language: Английский

Citations

0
Multistimuli Responsive Behaviors of Salicylaldehyde Hydrazone Zn(II) Complexes in Solution, Solid State, and PMMA Film DOI

Han–Wen Zheng,

Min Wu,

Su-Jia Liu

et al.

Crystal Growth & Design, Journal Year: 2025, Volume and Issue: unknown

Published: March 4, 2025

Zn(II) complexes based on salicylaldehyde hydrazone ligands have emerged as a promising class of stimuli-responsive luminescent materials. Herein, three complexes, namely, [Zn2(HL1)2(py)2]·H2O (1a), Zn2(HL1)2(py)2 (1b), and Zn2(HL2)2(py)2 (2), were synthesized by self-assembly with under solvothermal conditions. Complexes 1a 2 exhibit reversible mechanochromic luminescence (MCL) during grinding fuming processes due to the transformation between crystalline phase amorphous phase. In addition, slight induces crystal from 1b. Comprehensive structural analysis experimental results indicate that may destroy coordination bond, leading dissociation pyridine molecule metal center. Besides, existence weak interaction molecules is easy upon external mechanical force, resulting in MCL high contrast. Moreover, DMSO solutions both turn yellow colorless accompanied quenching after irradiating white light. shows photochromism switching light 365 nm UV illumination short response time, while prolonged irreversible response, potentially attributed steric hindrance effects. However, complex exhibits more obvious photochromic property solid state than 1a. Its color changes brown irradiation light, formation radicals generated photoinduced electron transfer hydroxyl oxygen atom coordinating molecule. The PMMA film also stimuli or These exhibiting properties, demonstrate significant potential advanced multistimuli responsive materials for various applications.

Language: Английский

Citations

0
Tuning the optical properties of pyrimidine-thiophene derivatives via molecular engineering DOI

Wenxiu Guo,

Huanda Ding,

Ao‐Mei Li

et al.

New Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The development of dual-state emission luminogens (DSEgens), which exhibit strong in solution and aggregated states, holds great promise for various practical applications due to their persistent fluorescence signals.

Language: Английский

Citations

0