Insight into the mechanism and outcoupling enhancement of excimer-associated white light generation

Chen, Ying-Hsiao; Tang, Kuo‐Chun; Chen, Yi-Ting; Shen, Jau-Ji; Wu, Yu-Sin; Liu, Shih-Hung; Lee, Chun-Shu; Chen, Chang-Hsuan; Lai, Tzu-Yu; Tung, Shih‐Huang; Jeng, Ru‐Jong; Hung, Wen‐Yi; Jiao, Min; Wu, Chung‐Chih; Chou, Pi‐Tai

doi:10.1039/c5sc04902d

Cited by 119 publications

(75 citation statements)

References 41 publications

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“…Organic fluorescence molecules that exhibit the excited state intramolecular proton transfer (ESIPT) process have been extensively investigated, which own extremely large Stokes shifts with the classical four‐level photochemical cycle . In general, such kind of cycles have been observed in most aromatic molecular systems with proton acceptor and donor moieties bridged with a pre‐existing intramolecular hydrogen bond.…”

Section: Introductionmentioning

confidence: 97%

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

Zhang

Cheng

et al. 2019

J of Physical Organic Chem

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Given that molecular excited state dynamical process plays important roles in designing and developing novel applications in recent years. In this work, based on density functional theory (DFT) and time‐dependent density functional theory (TDDFT) methods, we theoretically explored the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol (HBT‐Cz) system about its excited state behaviors. Via simulating the electrostatic potential surface (EPS) of HBT‐Cz structure, we confirm the formation of intramolecular hydrogen bond O2—H3···N4 in the S0 state. Our theoretical dominating bond lengths, bond angles, and the infrared (IR) vibrational spectra involved in hydrogen bond demonstrate that O2—H3···N4 should be strengthened in the S1 state. Upon the photoexcitation, we find the charge transfer characteristics around hydrogen bonding moieties play important roles in facilitating excited state intramolecular proton transfer (ESIPT) process. Via constructing potential energy curves, we confirm the ESIPT reaction that further explains previous experimental phenomenon. Moreover, we also search the S1‐state transition state (TS) structure along with ESIPT path, based on which we simulate the intrinsic reaction coordinate (IRC) path. Combing with the atom‐centered density matrix propagation (ADMP) molecular dynamics simulation, we further confirm the ESIPT mechanism presented in this work. We sincerely hope that our theoretical work could guide novel applications based on HBT‐Cz system in future.

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Section: Introductionmentioning

confidence: 97%

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

Zhang

Cheng

et al. 2019

J of Physical Organic Chem

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“…And generally, this kind of significant Stokes shift could be as large as 6000 to 12 000 cm −1 . The development of novel materials for chemical sensing, optoelectronics, cell imaging, white LEDs, molecular switches, and so forth was because of this kind of property …”

Section: Introductionmentioning

confidence: 99%

Investigation on the excited state intramolecular proton transfer process for the novel 2‐(3,5‐dichloro‐2‐hydroxy‐phenyl)‐benzooxazole‐5‐carboxylicacid system

Gao

Yang

Zhang

et al. 2019

J of Physical Organic Chem

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In view of the importance of excited state hydrogen bonding interactions and excited state proton transfer (ESPT) dynamical behaviors, in this work, we theoretically explore the excited state process for a novel 2‐(3,5‐dichloro‐2‐hydroxy‐phenyl)‐benzooxazole‐5‐carboxylicacid (DHPBC) system. On the basis of discrete Fourier transform (DFT) and time‐dependent density functional theory (TDDFT) methods, we reappear previous experimental reports with checking the reasonability of our theoretical level. We calculate and compare the primary geometrical parameters and hydrogen bonding energies around hydrogen bonding moieties, which reveals that the intramolecular hydrogen bond OH···N of DHPBC is enhanced in the S1 state. The increased electron densities around N atom contribute to attracting proton of hydroxyl upon the photoexcitation, which plays important roles in strengthening hydrogen bond and in facilitating excited state intra‐ or intermolecular proton transfer (ESIPT) process. Via constructing potential energy curves along with the ESIPT path, we verify that the ESIPT process of DHPBC system is ultrafast because of the low potential energy barrier. That should be the reason why the normal emission of DHPBC cannot be detected in previous experiment. This work not only clarifies the excited state hydrogen bonding interactions and fills the vacancy of specific ESIPT mechanism for DHPBC system in experiment, but also explains the fluorescence quenching phenomenon.

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“…[16][17][18][19][20] The fluorescence band of the initial enol form exhibits a normal Stokes shift, whereas that of proton transfer tautomer keto structure has a more significant Stokes shift than the enol structure. [39,40] Particularly, white-light-emitting organic materials have drawn great attention recently owing to their potential applications. [21][22][23][24][25][26] Because of the drastic structural alternations, the tautomer possesses photochemical and photophysical properties that are different from those of the original (enol) structure, offering versatilities in a variety of applications such as optical filters, molecular switches, laser materials, UV photostabilizers, fluorescence sensors, and so on.…”

Section: Introductionmentioning

confidence: 99%

A detailed theoretical study on the excited‐state hydrogen‐bonding dynamics and the proton transfer mechanism for a novel white‐light fluorophore

Gao

Yang

Jia

et al. 2018

J Chinese Chemical Soc

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In this work, density functional theory (DFT) and time‐dependent DFT (TDDFT) methods were used to investigate the excited‐state dynamics of the excited‐state hydrogen‐bonding variations and proton transfer mechanism for a novel white‐light fluorophore 2‐(4‐[dimethylamino]phenyl)‐7‐hyroxy‐6‐(3‐phenylpropanoyl)‐4H‐chromen‐4‐one (1). The methods we adopted could successfully reproduce the experimental electronic spectra, which shows the appropriateness of the theoretical level in this work. Using molecular electrostatic potential (MEP) as well as the reduced density gradient (RDG) versus the product of the sign of the second largest eigenvalue of the electron density Hessian matrix and electron density (sign[λ2]ρ), we demonstrate that an intramolecular hydrogen bond O1–H2···O3 should be formed spontaneously in the S0 state. By analyzing the chemical structures, infrared vibrational spectra, and hydrogen‐bonding energies, we confirm that O1–H2·O3 should be strengthened in the S1 state, which reveals the possibility of an excited‐state intramolecular proton transfer (ESIPT) process. On investigating the excitation process, we find the S0 → S1 transition corresponding to the charge transfer, which provides the driving force for ESIPT. By constructing the potential energy curves, we show that the ESIPT reaction results in a dynamic equilibrium in the S1 state between the forward and backward processes, which facilitates the emission of white light.

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Insight into the mechanism and outcoupling enhancement of excimer-associated white light generation

Abstract: Fundamental insight into excimer formation of Cz9PhAn, achieving a single-component, high-performance WOLED.

Cited by 119 publications

References 41 publications

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

Investigation on the excited state intramolecular proton transfer process for the novel 2‐(3,5‐dichloro‐2‐hydroxy‐phenyl)‐benzooxazole‐5‐carboxylicacid system

A detailed theoretical study on the excited‐state hydrogen‐bonding dynamics and the proton transfer mechanism for a novel white‐light fluorophore

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