An analogy study on ESIPT reaction for 3BHC sensor between polar DMF and nonpolar toluene

2017 ◽  
Vol 95 (12) ◽  
pp. 1303-1307
Author(s):  
Dapeng Yang ◽  
Min Jia ◽  
Jingyuan Wu ◽  
Xiaoyan Song ◽  
Qiaoli Zhang
Keyword(s):  
Excited State ◽  
Density Functional ◽  
Emission Spectra ◽  
Dft Method ◽  
Intramolecular Proton Transfer ◽  
Nonpolar Solvent ◽  
State Behavior ◽  
Functional Theory ◽  
Td Dft ◽  
Intramolecular Hydrogen

A comparison about excited state intramolecular proton transfer (ESIPT) mechanism of a new sensor 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde (3BHC) in polar solvent dimethylformamide (DMF) and nonpolar solvent toluene have been investigated within the framework of the time-dependent density functional theory (TD-DFT) method. The reproduced previous experimental absorption and emission spectra via our calculations reveals the reasonability of the DFT and TD-DFT theoretical level. The staple bond lengths, bond angles, and corresponding infrared vibrational spectra demonstrate that the intramolecular hydrogen bond of 3BHC should be strengthened in both polar DMF and nonpolar toluene. Two kinds of ESIPT mechanisms for different solvents have been put forward; there is a low potential barrier in the ESIPT process in the DMF solvent, whereas there is almost a nonbarrier for the ESIPT process in the toluene solvent. Hence, we could conclude that the ESIPT process of 3BHC sensor is more likely to occur in the nonpolar solvent upon the photoexcitation, based on which, the excited state behavior of 3BHC could be controlled.

Theoretical study of the ground and excited states of 1-methylamideanthraquinone and its complex with fluoride anion

2016 ◽  
Vol 15 (04) ◽  
pp. 1650033
Author(s):  
Bing-Qiang Wang ◽  
Xiao-Fen Yin ◽  
Yan-Yun Dong ◽  
Cai-Yun Zhang
Keyword(s):  
Density Functional Theory ◽  
Hydrogen Bond ◽  
Proton Transfer ◽  
Density Functional ◽  
Intermolecular Hydrogen Bond ◽  
Emission Spectra ◽  
Intramolecular Proton Transfer ◽  
Fluoride Anion ◽  
Functional Theory ◽  
Intramolecular Hydrogen

We have performed a series of calculations using density functional theory (DFT) and time-dependent density functional theory (TD-DFT) for 1-methylamideanthraquinone (MAAQ). In the S0 state of MAAQ, amide group is coplanar with anthraquinone, and an intramolecular hydrogen bond [Formula: see text] is formed. The [Formula: see text] transition has an intramolecular charge transfer character. Two stable structures (planar nMAAQ and twisted tMAAQ) have been obtained in the S1 state of MAAQ. Thereinto, nMAAQ is lower by 0.105[Formula: see text]eV than tMAAQ in energy, so nMAAQ is the dominant conformation in the S1 state of MAAQ and the emission spectra of tMAAQ cannot be observed in the solution of MAAQ. Excited state intramolecular proton transfer (ESIPT) between C[Formula: see text]O and N–H was not observed in the S1 state of MAAQ. Upon addition of fluoride anion, only twisted conformations were obtained in both S0 and S1 states of MAAQ-F[Formula: see text]. An intermolecular hydrogen bond [Formula: see text] is formed in the S0 state, and intermolecular proton transfer happens in the S1 state for MAAQ-F[Formula: see text].

scholarly journals Nitrile-Substituted 2-(Oxazolinyl)-Phenols: Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Fluorophores

2020 ◽  
Author(s):  
Dominik Göbel ◽  
Daniel Duvinage ◽  
Tim Stauch ◽  
Boris Nachtsheim
Keyword(s):  
Excited State ◽  
Solid State ◽  
Proton Transfer ◽  
Density Functional ◽  
Intramolecular Proton Transfer ◽  
Crystal Structure Analysis ◽  
Quantum Yields ◽  
Functional Theory ◽  
Emission Properties ◽  
Emission Enhancement

Herein, we present minimalistic single-benzene, excited-state intramolecular proton transfer (ESIPT) based fluorophores as powerful solid state emitters. The very simple synthesis gave access to all four regioisomers of nitrile-substituted 2(oxazolinyl)phenols (MW = 216.1). In respect of their emission properties they can be divided into aggregation-induced emission enhancement (AIEE) luminophores (1-CN and 2-CN), dual state emission (DSE) emitters (3-CN) and aggregation-caused quenching (ACQ) fluorophores (4‐CN). Remarkably, with compound 1-CN we discovered a minimalistic ESIPT based fluorophore with extremely high quantum yield in the solid state ΦF = 87.3% at λem = 491 nm. Furthermore, quantum yields in solution were determined up to ΦF = 63.0%, combined with Stokes shifts up till 11.300 cm–1. Temperature dependent emission mapping, crystal structure analysis and time-dependent density functional theory (TDDFT) calculations gave deep insight into the origin of the emission properties.<br>

scholarly journals 8-(Pyridin-2-yl)quinolin-7-ol as a Platform for Conjugated Proton Cranes: A DFT Structural Design

Micromachines ◽  
2020 ◽  
Vol 11 (10) ◽  
pp. 901 ◽  
Author(s):  
Anton Georgiev ◽  
Liudmil Antonov
Keyword(s):  
Excited State ◽  
Structural Design ◽  
Density Functional ◽  
Intramolecular Proton Transfer ◽  
State Density ◽  
Strong Electron ◽  
Functional Theory ◽  
Substituted Pyridines ◽  
Donor Acceptor ◽  
Enol Tautomer

Theoretical design of conjugated proton cranes, based on 7-hydroxyquinoline as a tautomeric sub-unit, has been attempted by using ground and excited state density functional theory (DFT) calculations in various environments. The proton crane action request existence of a single enol tautomer in ground state, which under excitation goes to the excited keto tautomer through a series of consecutive excited-state intramolecular proton transfer (ESIPT) steps with the participation of the crane sub-unit. A series of substituted pyridines was used as crane sub-units and the corresponding donor-acceptor interactions were evaluated. The results suggest that the introduction of strong electron donor substituents in the pyridine ring creates optimal conditions for 8-(pyridin-2-yl)quinolin-7-ols to act as proton cranes.

scholarly journals Surface-enhanced Raman scattering of pyrazine on Au5Al5 bimetallic nanoclusters

RSC Advances ◽  
2017 ◽  
Vol 7 (20) ◽  
pp. 12170-12178 ◽  
Author(s):  
Quanjiang Li ◽  
Qianqian Ding ◽  
Weihua Lin ◽  
Jiangcai Wang ◽  
Maodu Chen ◽  
...  
Keyword(s):  
Density Functional ◽  
Dft Method ◽  
Time Dependent ◽  
Functional Theory ◽  
Bimetallic Nanoclusters ◽  
Surface Enhanced ◽  
Td Dft ◽  
Surface Enhanced Raman ◽  
Enhanced Raman Scattering ◽  
Dependent Density

In this study, we theoretically investigated the Raman and absorption spectra of pyrazine adsorbed on Au5Al5 bimetallic nanoclusters by a time-dependent density functional theory (TD-DFT) method.

DFT Study of Substituted Effect on Absorption and Emission Spectra of Naphthoquinone Derivatives

2011 ◽  
Vol 233-235 ◽  
pp. 1878-1883 ◽  
Author(s):  
Li Zhi Wang ◽  
Run Zhou Su ◽  
Shuo Qi ◽  
Wei Yu Gong ◽  
Tai Min Cheng
Keyword(s):  
Excited State ◽  
Density Functional ◽  
Visible Region ◽  
Emission Spectra ◽  
Electron Transition ◽  
Functional Theory ◽  
Absorption And Emission ◽  
Absorption And Emission Spectra ◽  
The Density Functional Theory ◽  
Substituted Effect

The density functional theory (DFT) is used to compute the ground-state geometries of naphthoquinone derivatives, and lowest singlet excited-state geometries of them have been investigated by the singles configuration interaction (CIS) method. The absorption and emission spectra are calculated by time-dependent DFT (TDDFT) on the basis of the ground- and excited-state geometries, respectively. Our calculations are in good agreement with the available experimental results. The calculated results show that with the introduction of hydroxyl the red-shift was found in the absorption and emission, and the range of spectra reach the visible region. Furthermore, in the absorptions electron transition type was identified from the point-view of molecular orbitals. Study of the effect of hydroxyl and site on spectra can provide the helpful information on further designing molecular devices.

Competitive excited-state single or double proton transfer mechanisms for bis-2,5-(2-benzoxazolyl)-hydroquinone and its derivatives

2015 ◽  
Vol 17 (18) ◽  
pp. 11990-11999 ◽  
Author(s):  
Jinfeng Zhao ◽  
Junsheng Chen ◽  
Jianyong Liu ◽  
Mark R. Hoffmann
Keyword(s):  
Density Functional Theory ◽  
Excited State ◽  
Proton Transfer ◽  
Density Functional ◽  
Intramolecular Proton Transfer ◽  
Time Dependent ◽  
Functional Theory ◽  
Double Proton Transfer ◽  
Transfer Mechanisms ◽  
Dependent Density

The excited state intramolecular proton transfer (ESIPT) mechanism of HBO, BBHQ and DHBO have been investigated using time-dependent density functional theory (TDDFT).

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