Flexible control of excited state transition under pressure/temperature: distinct stimuli-responsive behaviours of two ESIPT polymorphs

Li, Aisen; Líu, Hao; Song, Chongping; Geng, Yijia; Xu, Shuping; Zhang, Hongyu; Zhang, Houyu; Cui, Haining; Xu, Weiqing

doi:10.1039/c9qm00395a

Cited by 21 publications

(10 citation statements)

References 70 publications

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“…This phenomenon is observed in the case of fluorescent materials with ESIPT stabilized through intermolecular H-bonds when a conversion from the excited keto form to the excited enol form is occurred. 93 This conversion results from the fact that, in this temperature range, the enol form is more stable than the keto form. Abnormally, this intensity decrease is also observed for the broad-band centred at 490 nm.…”

Section: Resultsmentioning

confidence: 99%

Organically tuned white-light emission from two zero-dimensional Cd-based hybrids

et al. 2022

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Section: Resultsmentioning

confidence: 99%

Organically tuned white-light emission from two zero-dimensional Cd-based hybrids

et al. 2022

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“…As previously commented, the absorption and emission spectra of thin films revealed similar features to the results of solution studies. The meta molecule 3b presented a higher QY, a shorter maximum wavelength, and a narrower emission, which suggests a more planar molecular orientation, together with a closer intermolecular packing, ,,, in comparison to the para isomer 3a . It should be recalled that this is also in consonance with the calculated geometry of the molecules (Supporting Information).…”

Section: Computational Studiesmentioning

confidence: 99%

“…In terms of ESIPT molecules, very few studies have been performed to analyze the effect of temperature or other extrinsic conditions on the emission properties of thin films. In particular, temperatures above room temperature were reported to induce a change in the FL of the ESIPT emission, but these studies were performed either in solution or the bulk solid state (i.e., powder or crystal). − To the best of our knowledge, the effect of thermal annealing on ESIPT thin films has not been studied, which, together with morphological analysis, is of relevant interest for different applications such as optoelectronic or photovoltaic devices.…”

Section: Introductionmentioning

confidence: 99%

Balancing the Push–Pull Effect on the Synthesis and Fluorescent Properties of New ESIPT Dyes for Thin Film Applications

Arenhart Soares,

Martinez-Denegri,

Baptista

et al. 2023

J. Phys. Chem. C

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The development of functional materials exploiting excited-state intramolecular proton transfer (ESIPT) requires a deep understanding of the push−pull balance on their reactivity, emission mechanism, and response to the surrounding environment. In this study, we focused on the model 2-(2-hydroxyphenyl)benzothiazole (HBT) core, and we have developed a simplified synthetic pathway to obtain two new ESIPT dyes with amide groups at the para or meta positions of the phenolic ring. We studied the impact of the geometry of the push−pull system for the two HBT isomers, unraveling that it strongly influenced their reactivity patterns and fluorescence emission. The ESIPT emission of the new molecules in the solution was affected by the solvent polarity, transitioning from pure keto to pure enol emission as the solvent polarity was increased. In the spin-coated films, the intermolecular interactions generated by the push−pull balance and the molecular shape of the deposited materials were also found to be essential for defining their morphology and the related emissive properties. Furthermore, these features were tuned by applying thermal annealing or by changing the solvent used for thin film deposition. The combination of both strategies was employed to provide a more favorable molecular ordering and to increase the fluorescence quantum yield of the neat films by 150%.

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“…molecular switch, dye lasers, organic light-emitting devices, photo stabilizers and others [3,4]. The ESIPT process is a photochemical operation which produces a tautomer with a completely different rst excited state electronic structure [5]. The initial excited state of the enol form has a uorescence spectrum with a short wavelength; while the its tautomer, the keto form, has a longer wavelength uorescence band, as a result of the proton transfer [6].…”

Section: Introductionmentioning

confidence: 99%

Substituent and Solvent Effects on Excited-State Intramolecular Proton Transfer Reactions of Orotic and Isoorotic Azo Dyes

Elroby

Aloufi

Aziz

et al. 2022

Preprint

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This study provides a complete analysis of the electronic and photophysical properties of orotic (OA) and isoorotic (IOA) azo dyes. The ability of the dye to work as an excited state intramolecular proton transfer (ESIPT) was investigated by using Density Functional Theory (DFT) and Time Dependent Density Functional Theory (TD-DFT) methods. The effect of electron-donating substituents (CH3 and NMe2) and an electron-withdrawing one (NO2) was examined. In addition, the effect of the solvent polarity on the ESIPT process is studied. All the geometrical structures in the singlet ground (S0) and excited (S1) states, were optimized using B3LYP/6-311+G** level of theory. The intramolecular hydrogen bond parameters (IHBs), and the Infra-Red vibrational analysis of the O-H bond show that the IHBs are enhanced in the S1 state. Furthermore, the absorption spectra were simulated and the values of stokes shifts were observed. The PAIOA derivative with an electron withdrawing group shows large stokes shift compared with those having electron-donating ones. Therefore, we can safely conclude that the substitutents groups and the different solvents are extremely impactful on the ESIPT process.

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Flexible control of excited state transition under pressure/temperature: distinct stimuli-responsive behaviours of two ESIPT polymorphs

Abstract: The conversion between normal emission and ESIPT can be successfully achieved under pressure and temperature.

Cited by 21 publications

References 70 publications

Organically tuned white-light emission from two zero-dimensional Cd-based hybrids

Organically tuned white-light emission from two zero-dimensional Cd-based hybrids

Balancing the Push–Pull Effect on the Synthesis and Fluorescent Properties of New ESIPT Dyes for Thin Film Applications

Substituent and Solvent Effects on Excited-State Intramolecular Proton Transfer Reactions of Orotic and Isoorotic Azo Dyes

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