Regulating the excited state behaviors of 2-benzooxazol-2-yl-4,6-di-tert-butyl-phenol fluorophore by solvent polarity: A theoretical simulation

Yang, Dapeng; Yang, Wenpeng; Tian, Yanshan; Zheng, Rui

doi:10.1016/j.chemphys.2022.111513

Cited by 12 publications

(4 citation statements)

References 68 publications

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“…The slight variation of the structures in different solvents will cause the disparity for LUMO energy values (Tables S27–S29). , Therefore, the molecule shows different energy emission bands from various excited-state emission colors. In the excited state, the calculation result of BDIBD shows that the distances between the hydrogen bonds of −O–H···N are 1.70440 Å in MeCN, 1.70671 Å in DCM, and 1.70448 Å in MeOH (MeCN ∼ MeOH < DCM).…”

Section: Results and Discussionmentioning

confidence: 99%

“…Meanwhile, ESIPT progress is related to the energy difference pertaining to the locally excited state and the relaxed excited state, which is greatly dependent on environmental conditions like solvents and so on. In order to clarify the occurrence sequence and efficiency mechanisms of the dual-proton transfer progress in these molecules, deeper exploration is needed from both the experimental and theoretical views. − …”

Section: Introductionmentioning

confidence: 99%

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Interplay of Dual-Proton Transfer Relay to Achieve Full-Color Panel Luminescence in Excited-State Intramolecular Proton Transfer (ESIPT) Fluorophores

et al. 2023

ACS Appl. Mater. Interfaces

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A new design was applied for the facile synthesis of pure organic photoluminescent molecules with dual excited-state intramolecular proton transfer (ESIPT) sites. In this novel class of emitters, full-color panel emission from blue, green, and yellow to red, including white light, can be achieved in different solvents as modulated by the enol−keto(1st)−keto(2nd) tautomer emissions. A comprehensive transient photophysical study verifies that keto(1st) and keto(2nd) have a precursor (<0.8 ps)− successor (∼20 ps)-relayed absorbance relationship, and then a fast equilibrium between the two is established, resulting in dual emissions in the nanosecond scale (∼1900 ps). Through the research on copper ions' selective PL response, the dual-ESIPT mechanism was further verified; in addition, the study of solid-state PL changes upon the stimulus of organic vapor manifests the potential application sensitivity of the molecules as dual-ESIPT sensors. Theoretical results including reaction potential energy surface analyses manifest the fact that dual-proton transfer goes along a sequential route with a smaller energy barrier, firmly supporting the experimental results. An intrinsic system that undergoes intramolecular double proton relayed transfer is thus established for the achievement of much broadened optical responses and full-color display, providing reference for the design and application of advanced dual-ESIPT optical materials.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Interplay of Dual-Proton Transfer Relay to Achieve Full-Color Panel Luminescence in Excited-State Intramolecular Proton Transfer (ESIPT) Fluorophores

et al. 2023

ACS Appl. Mater. Interfaces

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“…FMOs are an efficient approach for acquiring changes in molecular charge distribution before and after photoexcitation [47,48]. Figure 7 visually shows the electron density distribution of HTP-1 and HTP-2 at the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO).…”

Section: Frontier Molecular Orbitals (Fmos)mentioning

confidence: 99%

Modulating the ESIPT Mechanism and Luminescence Characteristics of Two Reversible Fluorescent Probes by Solvent Polarity: A Novel Perspective

Wang,

Mu,

Sun

et al. 2024

Molecules

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As reversible fluorescent probes, HTP-1 and HTP-2 have favourable applications for the detection of Zn2+ and H2S. Herein, the impact of solvent on the excited-state intramolecular proton transfer (ESIPT) of HTP-1 and HTP-2 was comprehensively investigated. The obtained geometric parameters and infrared (IR) vibrational analysis associated with the intramolecular hydrogen bond (IHB) indicated that the strength of IHB for HTP-1 was weakened in the excited state. Moreover, structural torsion and almost no ICT behaviour indicated that the ESIPT process did not occur in HTP-1. Nevertheless, when the 7-nitro-1,2,3-benzoxadiazole (NBD) group replaced the H atom, the IHB strength of HTP-2 was enhanced after photoexcitation, which inhibited the twisting of tetraphenylethylene, thereby opening the ESIPT channel. Notably, hole-electron analysis and frontier molecular orbitals revealed that the charge decoupling effect was the reason for the fluorescence quenching of HTP-2. Furthermore, the potential energy curves (PECs) revealed that HTP-2 was more inclined to the ESIPT process in polar solvents than in nonpolar solvents. With a decrease in solvent polarity, it was more conducive to the ESIPT process. Our study systematically presents the ESIPT process and different detection mechanisms of the two reversible probe molecules regulated by solvent polarity, providing new insights into the design and development of novel fluorescent probes.

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“…Solvent-dependent ESIPT emission was early reported by Nagaoka et al for o-hydroxybenzaldehyde (OHBA) [26] and Mitra and Das on 4methyl-2,6-diformylphenol (MFOH) [27]. For example, in a polar solvent, the dual fluorescence at 460 and 520 nm of MFOH originated from a hydrogen-bonded open-form complex and an anion form, respectively.…”

mentioning

confidence: 93%

Efficient excited‐state intramolecular proton transfer in acridone derivatives—A case study of Paratrimerin C

Nguyen

Truong

Ngo

et al. 2022

Int J of Quantum Chemistry

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Paratrimerin C is a natural acridone antioxidant that is also potent as an anti‐UV agent. The photophysical process of Paratrimerin C, including the absorption and emission and the excited state intramolecular proton transfer (ESIPT) mechanism, is studied herein with time‐dependent density functional theory. The solvent effect on ESIPT is studied for polar (water) and non‐polar (benzene) solvents employing the Integral Equation Formalism Polarization Continuum Model and adding up to three explicit molecules of solvent. The normal and tautomer forms of the Paratrimerin C at the ground‐ and excited‐state structures are studied at the M06‐2X/6‐311++G(d,p) level of theory. The potential energy curves along the reaction coordinates indicate that the ESIPT is a barrier‐less reaction, and the variation of OdOa distance in the excited state shows significant molecular structure deformation along the proton transfer process following the normal‐to‐tautomerism pathway. The obtained results suggest using of acridone derivatives as efficient and tunable fluorescence molecules besides their biological activities.

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Regulating the excited state behaviors of 2-benzooxazol-2-yl-4,6-di-tert-butyl-phenol fluorophore by solvent polarity: A theoretical simulation

Cited by 12 publications

References 68 publications

Interplay of Dual-Proton Transfer Relay to Achieve Full-Color Panel Luminescence in Excited-State Intramolecular Proton Transfer (ESIPT) Fluorophores

Interplay of Dual-Proton Transfer Relay to Achieve Full-Color Panel Luminescence in Excited-State Intramolecular Proton Transfer (ESIPT) Fluorophores

Modulating the ESIPT Mechanism and Luminescence Characteristics of Two Reversible Fluorescent Probes by Solvent Polarity: A Novel Perspective

Efficient excited‐state intramolecular proton transfer in acridone derivatives—A case study of Paratrimerin C

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