Photoinduced excited state intramolecular proton transfer and spectral behaviors of Aloesaponarin 1

Yang, Yonggang; Liu, Yufang; Yang, Dapeng; Li, Hui; Jiang, Kai; Sun, Jinfeng

doi:10.1016/j.saa.2015.07.046

Cited by 49 publications

(23 citation statements)

References 47 publications

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“…The IR spectra of NHM‐HSO 4 − complex and NHMH + cation were calculated theoretically for S 0 and S 1 states with the same theoretical model (Figure ). To shed light on the NHM‐HSO 4 − complexation mechanism, the N−H stretching frequency for NHMH + moiety was calculated for S 0 and S 1 states to compare the same with that of NHM‐bisulfate complex . We assume natural pyridinic ‐N−H bond formation in NHMH + providing stretching frequencies 3590 cm −1 in S 0 and 3648 cm −1 S 1 states respectively.…”

Section: Resultsmentioning

confidence: 99%

A Molecular Lock with Hydrogen Sulfate as “Key” and Fluoride as “Hand”: Computing Based Insights on the Functioning Mechanism

et al. 2016

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The present work demonstrates a new fully regenerative, molecular machine-like "ON-OFF-ON" chemosensor based on a b-carboline molecule "OFF-ON-OFF" cycle. It behaves as a molecular lock that requires a hydrogen sulfate (HSO 4 À ) ion as"key" to open the lock and a fluoride (F À ) ion as "hand" that removes the key from the lock to close the lock. The reversibility and reusability of sensor for the detection of hydrogen sulfate and fluoride ions were tested for six cycles. Experimental and computational studies reveal that the proton transfer process from hydrogen sulfate (HSO 4 À ) ion to the pyridinic nitrogen atom of norharmane leading to the formation of a hydrogen bonded ion pair (HBIP) provides the optical changes in the visible region that are advantageous for real time and on-site application.[a] S.

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Section: Resultsmentioning

confidence: 99%

A Molecular Lock with Hydrogen Sulfate as “Key” and Fluoride as “Hand”: Computing Based Insights on the Functioning Mechanism

et al. 2016

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“…The corresponding absorption and fluorescence values have been listed in Table 2. The TDDFT has been confirmed as reliable theoretical method for ESIPT reactions of title compound, since these theoretical values calculated by B3LYP, PBE0 and M06 methods are great consistent with experimental [43][44][59][60][61][62][63]. Therefore, in this study, we only select the computational results of B3LYP method to discuss in detail.…”

Section: Geometric Configurations and Electronic Spectramentioning

confidence: 95%

“…Electrostatic potential (ESP) also reveals the position and size of intra-and inter-molecular hydrogen bond interactions through visual scalable colours [44,[64][65]. The colour gradient from red, green to blue represents the increasing of ESP, which is related to the changes of electron density.…”

Section: Geometric Configurations and Electronic Spectramentioning

confidence: 99%

“…The practical applications of proton transfer become more and more extensive, for instance UV filters, LEDs, fluorescence sensors, molecular switches, laser dyes, etc. [33][34][35][36][37][38][39][40][41][42][43][44][45]. Due to knowledge of excited-state hydrogen bond has been little understood at present, so the characters of excited state hydrogen bonds are still difficult to be clearly explained.…”

Section: Introductionmentioning

confidence: 99%

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The theoretical study of excited-state intramolecular proton transfer of 2,5-bis(benzoxazol-2-yl)thiophene-3,4-diol

Lan

Yang

et al. 2017

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Ever since the seminal experimental observation of the excited-state intramolecular proton transfer (ESIPT) reaction of methyl salicylate (MS) by Weller et al in the middle of the last century [1], the phenomenon of photoinduced proton transfer process has attracted countless works in many fields of chemistry and molecular biology [2][3][4][5][6][7][8][9][10][11][12][13][14][15]. A very fascinating feature of molecules undergoing ESIPT is the presence of a strong intramolecular hydrogen bond, in which the acidity and basicity relations can be controllable by photoexcitation.…”

Section: Introductionmentioning

confidence: 99%

TDDFT assessment of excited state intramolecular proton transfer in a panel of chromophore 2-hydroxypyrene-1-carbaldehyde

Shi¹

2016

JAMS

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Abstract. Time dependent density functional theory method at the def-TZVP/B3LYP level was employed to investigate excited state intramolecular proton transfer (ESIPT) properties of 2-hydroxypyrene-1-carbaldehyde (HC). Our calculated results of the primary bond lengths and infrared vibrational spectroscopic information show that, upon photoexcitation, the intramolecular hydrogen bond is significantly strengthened in S 1 state, which facilitates the proton transfer process effectively. Furthermore, the electron density distributions of frontier molecular orbitals were demonstrated to be a positive factor for the ESIPT. By the monitor of the characteristic peaks stretching vibration of O-H group in the IR spectra, we have further confirmed the occurrence of ESIPT. The constructed potential energy surface of the S 1 state has also been used to explain the proton transfer process and evaluate the radiationless pathway, indicating that the ESIPT process occurs most easily in HC molecule. PACS: 33.15.Fm

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Photoinduced excited state intramolecular proton transfer and spectral behaviors of Aloesaponarin 1

Cited by 49 publications

References 47 publications

A Molecular Lock with Hydrogen Sulfate as “Key” and Fluoride as “Hand”: Computing Based Insights on the Functioning Mechanism

A Molecular Lock with Hydrogen Sulfate as “Key” and Fluoride as “Hand”: Computing Based Insights on the Functioning Mechanism

The theoretical study of excited-state intramolecular proton transfer of 2,5-bis(benzoxazol-2-yl)thiophene-3,4-diol

TDDFT assessment of excited state intramolecular proton transfer in a panel of chromophore 2-hydroxypyrene-1-carbaldehyde

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