Experimental and theoretical comprehension of ESIPT fluorophores based on a 2-(2′-hydroxyphenyl)-3,3′-dimethylindole (HDMI) scaffold

Stoerkler, Timothée; Ulrich, Gilles; Retailleau, Pascal; Laurent, Adèle D.; Jacquemin, Denis; Massue, Julien

doi:10.1039/d4sc01937g

Chem. Sci.

2024

DOI: 10.1039/d4sc01937g

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Experimental and theoretical comprehension of ESIPT fluorophores based on a 2-(2′-hydroxyphenyl)-3,3′-dimethylindole (HDMI) scaffold

Timothée Stoerkler,

Gilles Ulrich,

Pascal Retailleau

et al.

Abstract: ESIPT emission is associated with intense single or multiple fluorescence in the solid-state, along with enhanced photostability and sensitivity to the close environment. As a result, ESIPT probes are attractive...

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Exploring electron donor and acceptor effects: DFT analysis of ESIPT/GSIPT in 2-(oxazolinyl)-phenols for photophysical and luminophore enhancement

Panneerselvam,

Francis,

Nathiya

et al. 2024

The Journal of Chemical Physics

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Understanding excited-state intramolecular proton transfer (ESIPT) is essential for designing organic molecules to enhance photophysical and luminophore properties in the development of optoelectronic devices. In this context, an attempt has been made to understand the impact of substituents on the ESIPT process of 2-(oxazolinyl)-phenol. Electron donating (EDG: –NH2, –OCH3, and –CH3) and electron withdrawing (EWG: –Cl, –Br, –COOH, –CF3, –CN, and –NO2) substitutions have been computationally designed and screened through density functional theory (DFT) and time-dependent density-functional theory (TDDFT) calculations. Furthermore, the ground state intramolecular proton transfer and ESIPT mechanisms of these designed luminophores are explored using the transition state theory. The results reveal that molecules with EDG show higher absorption and emission peaks than molecules with EWG and also indicate that the mobility of charge carriers in 2-(oxazolinyl)-phenol derivatives is significantly influenced by substituents. We found that the EWGs decrease the reorganization energy and increase the vertical ionization potential and electron affinity values, as well as the highest occupied molecular orbital-lowest unoccupied molecular orbital gap, compared to the EDG substituted molecules. Significantly, the excited state (S1) of the keto emission (K) form shows notably larger values for the EDG substitutions. The intersystem crossing pathway efficiency weakens with reduced spin–orbit coupling matrix element in the enol form with electron-donating substituents and vice versa in the keto form during S1–T3 transitions. Our research links intramolecular proton transfers and triplet generation, making these substituted molecules appealing for optoelectronic devices. Introducing EDGs, such as –NH2, boosts the ESIPT reaction in 2-(oxazolinyl)-phenol. This study guides designing ESIPT emitters with unique photophysical properties.

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Exploring electron donor and acceptor effects: DFT analysis of ESIPT/GSIPT in 2-(oxazolinyl)-phenols for photophysical and luminophore enhancement

Panneerselvam,

Francis,

Nathiya

et al. 2024

The Journal of Chemical Physics

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Experimental and theoretical comprehension of ESIPT fluorophores based on a 2-(2′-hydroxyphenyl)-3,3′-dimethylindole (HDMI) scaffold

Abstract: ESIPT emission is associated with intense single or multiple fluorescence in the solid-state, along with enhanced photostability and sensitivity to the close environment. As a result, ESIPT probes are attractive...

Cited by 1 publication

References 59 publications

Exploring electron donor and acceptor effects: DFT analysis of ESIPT/GSIPT in 2-(oxazolinyl)-phenols for photophysical and luminophore enhancement

Exploring electron donor and acceptor effects: DFT analysis of ESIPT/GSIPT in 2-(oxazolinyl)-phenols for photophysical and luminophore enhancement

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