Insight into the excited-state intramolecular double-proton transfer of the 2,5-bis(benzoxazol-2-yl)thiophene-3,4-diol: one-step or stepwise mechanism?

Lu, Ming; Yang, Yunfan; Chu, Tianshu

doi:10.1007/s00214-017-2088-9

Cited by 11 publications

(3 citation statements)

References 61 publications

(64 reference statements)

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“…The electronic-emission spectra, displayed in Figure , are recorded to study the fluorescence properties of PTBE, M1, M2, and PTBE-TNT and to evaluate the current calculation levels . The emission wavelengths of the lowest-lying singlet excited state for each molecule are marked, and the corresponding experimental values are given in parentheses.…”

Section: Resultsmentioning

confidence: 99%

Reconsideration of the Detection and Fluorescence Mechanism of a Pyrene-Based Chemosensor for TNT

Zhou

et al. 2018

J. Phys. Chem. A

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The rapid detection of chemical explosives is crucial for national security and public safety, and the investigation of sensing mechanisms is important for designing highly efficient chemosensors. This study theoretically investigates the detection and fluorescence mechanism of a newly synthesized pyrene-based chemosensor for the detection of trinitrotoluene (TNT) through density-functional-theory (DFT) and time-dependent density-functional-theory (TDDFT) methods and suggests a different interaction product of the probe and TNT from previously reported ones [ Mosca et al. J. Am. Chem. Soc. 2015 , 137 , 7967 ]. Instead of forming Meisenheimer complexes, the energies of which are beyond those of the reactants, a low-energy product generated by a π-π-stacking interaction is more rational and favorable. The fluorescence-quenching property further confirms that the π-π-stacking product is the predicted one rather than luminescent Meisenheimer complexes. Frontier-molecular-orbital (FMO)-analysis results show that photoinduced electron transfer (PET) is the mechanism underlying the luminescence quenching of the probe upon exposure to TNT.

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Section: Resultsmentioning

confidence: 99%

Reconsideration of the Detection and Fluorescence Mechanism of a Pyrene-Based Chemosensor for TNT

Zhou

et al. 2018

J. Phys. Chem. A

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“…However, to mimic the situation in more complicated natural systems, the study of molecules with a single isolated ESIPT site is not sufficient. , Instead, the incorporation of multiple ESIPT sites into one single molecule might bring a more broadened photoluminescent range, enriched photophysical phenomena, and multi-stimulus optical responses. In particular, the deliberately designed dual-proton transfer ESIPT molecules could be useful for the development of a new generation of displaying and sensing devices based on their unique luminescence, with a simpler structure, better performance, and less energetic advantages through the use of a single fluorophore unit and double ESIPT sites. , While many different chromophores have been used for ESIPT emission, embedding this subtle photophysical process into a dual-proton transfer molecule still appears challenging. 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.…”

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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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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“…[33] Given that BBTD belongs to the model system about exploring excited state intramolecular double proton transfer process, many groups have theoretically probed into the excited state dynamical reactions for BBTD. [34][35][36][37][38][39] Till now, the stepwise dual proton transfer mechanism of BBTD could be verified. As the one ethyl substitution compound, 2,5-bis (benzoxazol-2-yl)thiophene-3,4-diol-ethyl (BBTE) contains one intramolecular HB wire that might occur the ESIPT reaction in solvents.…”

Section: Introductionmentioning

confidence: 99%

Theoretical unraveling detailed excited state proton transfer mechanism for 2,5‐bis (benzoxazol‐2‐yl)thiophene‐3,4‐diol‐ethyl compound in different solvents

Zhang

Wan

et al. 2021

J of Physical Organic Chem

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Excited state intramolecular proton transfer (ESIPT) of organic molecules has been drawing continuously considerable interests. It is not only one of the most basic processes in life but also exists in wide of application fields. In this work, we theoretically make a thorough inquiry about molecular excited state trends and ESIPT procedures for the novel highly miscible 2,5-bis (benzoxazol-2-yl)thiophene-3,4-diol-ethyl (BBTE) molecule. Based on DFT and TDDFT means, we first examine and certify hydrogen bond O1-H2ÁÁÁN3 role in BBTE.Probing into molecular structure and infrared (IR) vibrational behaviors, we validate O1-H2ÁÁÁN3 of BBTE is enhanced in S1 state via photo-induced excitation. Accessorial negative electronic densities over N3 atom facilitate attracting

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Insight into the excited-state intramolecular double-proton transfer of the 2,5-bis(benzoxazol-2-yl)thiophene-3,4-diol: one-step or stepwise mechanism?

Cited by 11 publications

References 61 publications

Reconsideration of the Detection and Fluorescence Mechanism of a Pyrene-Based Chemosensor for TNT

Reconsideration of the Detection and Fluorescence Mechanism of a Pyrene-Based Chemosensor for TNT

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

Theoretical unraveling detailed excited state proton transfer mechanism for 2,5‐bis (benzoxazol‐2‐yl)thiophene‐3,4‐diol‐ethyl compound in different solvents

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