Consistent Franck–Condon modeling of geometry changes for the S0→S1(ππ*) excitation in anthranilic acid: LIF spectroscopy aided by CC2 or TDDFT vibrations

Kolek, Przemysław; Andrzejak, Marcin; Uchacz, Tomasz; Szlachcic, Paweł

doi:10.1016/j.jqsrt.2019.106747

Cited by 4 publications

(4 citation statements)

References 47 publications

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“…DFT calculations have been performed with Becke’s three-parameter hybrid exchange–correlation functional (B3LYP) in IQmol version 2.14. , The B3LYP functional has the ability to produce reliable geometries and energies in many different systems. , Triple-ζ basis sets (6-31+G*) and one set of d polarization functions were selected. Benzenoid ( B ), quinoid: methylene quinone of ortho ( o Q ) and para ( p Q ), bezenoidortho quinoid ( B – o Q ), and bezenoid–para quinoid ( B – p Q ) structures were chosen (Figure S3) as DFT perturbations, and their ground-state geometry was optimized.…”

Section: Methodsmentioning

confidence: 99%

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Artificial Bifunctional Photozyme of Glucose Oxidase–Peroxidase for Solar-Powered Glucose–Peroxide Detection in a Biofluid with Resorcinol–Formaldehyde Polymers

Pramanik¹,

Sengupta²,

Majumder³

et al. 2020

ACS Appl. Mater. Interfaces

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Photozymes or artificial photosynthesis based on alternative natural enzymes is vital for the sustainable development of next-generation healthcare, energy, and materials science. Herein, we report resorcinol–formaldehyde (RF) resins as a solar-driven metal-free bifunctional glucose oxidase–peroxidase stand-alone photozyme for the colorimetric dual detection of hydrogen peroxide and glucose. The π-bond conjugated benzenoid–ortho/para quinoid RF polymers are efficient for glucose oxidation and hydrogen peroxide reduction with concurrent 3,3′,5,5′-tetramethylbenzidine oxidation under natural sunlight. The photoinduced colorimetric process could detect H2O2 up to 3.5 μM at 652 nm with the linear range of 0.1–2 mM. A limit of detection of 9.2 μM was exhibited by the system while measuring glucose with a linearity from 0.2 to 8.5 mM. The formation of hydroxyl radicals ( • OH) from glucose oxidation reactions was evidenced by spin trapping electron paramagnetic resonance studies conducted herein. The results indicated that RF resins possessed strong intrinsic glucose oxidase and peroxidase (POx)-like activity under natural sunlight with promising storage and operation. This simple photozyme will definitely have potential uses in biomimetic solar-driven catalysis, bioenergy, and biomedicine.

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Section: Methodsmentioning

confidence: 99%

“…43,44 The B3LYP functional has the ability to produce reliable geometries and energies in many different systems. 45,46…”

Section: Reaction Conditionsmentioning

confidence: 99%

Artificial Bifunctional Photozyme of Glucose Oxidase–Peroxidase for Solar-Powered Glucose–Peroxide Detection in a Biofluid with Resorcinol–Formaldehyde Polymers

Pramanik¹,

Sengupta²,

Majumder³

et al. 2020

ACS Appl. Mater. Interfaces

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“…The families of hydroxy carboxylic acids that have been exploited as proton transfer systems are hydroxyl-benzoic acids and esters [ 34 , 35 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 ], hydroxynaphthoic acids [ 71 , 72 , 73 , 74 , 75 ] and anthranilic acid and its esters [ 76 , 77 , 78 , 79 , 80 , 81 ]. Besides carboxylic acids, other compounds belonging to hydroxyflavones [ 82 , 83 , 84 ], quinoline family and anthraquiniones [ 85 , 86 , 87 ,…”

Section: Introductionmentioning

confidence: 99%

Excited-State Intramolecular Proton Transfer: A Short Introductory Review

2021

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In this short review, we attempt to unfold various aspects of excited-state intramolecular proton transfer (ESIPT) from the studies that are available up to date. Since Weller’s discovery of ESIPT in salicylic acid (SA) and its derivative methyl salicylate (MS), numerous studies have emerged on the topic and it has become an attractive field of research because of its manifold applications. Here, we discuss some critical aspects of ESIPT and tautomerization from the mechanistic viewpoint. We address excitation wavelength dependence, anti-Kasha ESIPT, fast and slow ESIPT, reversibility and irreversibility of ESIPT, hydrogen bonding and geometrical factors, excited-state double proton transfer (ESDPT), concerted and stepwise ESDPT.

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“…In this study, we aim to calculate the global reorganization energies associated with the investigated electronic transitions, reproduce the available experimental absorption and emission spectra of oligofurans, and identify the normal modes that contribute to the observed vibronic structures. To achieve these goals, we employ the density functional theory (DFT) and its time-dependent variant (TDDFT) using several representative exchange-correlation functionals, as well as the ab initio approach using the approximate coupled clusters singles and doubles model (CC2) [ 30 , 31 , 32 ] that has already proven successful in similar applications [ 33 , 34 , 35 , 36 , 37 , 38 ] and can currently be regarded as the method of choice for theoretical analysis of spectroscopic properties of medium-sized (containing several tens of heavy atoms) organic systems. In order to select the best XC functionals for our purposes, as well as to further test the performance of CC2, we first calculate the electronic transition energies and the related reorganization energies for the oligofurans containing from two to nine rings and compare them with the available experimental data [ 16 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

Optical Spectra of Oligofurans: A Theoretical Approach to the Transition Energies, Reorganization Energies, and the Vibronic Activity

2021

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There is experimental evidence of high vibronic activity that accompanies the allowed transition between the ground state and the lowest electronic singlet excited state of oligofurans that contain two, three, and four furan rings. The absorption and emission spectra of the three lowest oligofurans measured at liquid nitrogen temperature show distinct fine structures that are reproduced using the projection-based model of vibronic coupling (with Dushinsky rotation included) parameterized utilizing either Density Functional Theory (DFT, with several different exchange-correlation functionals) or ab initio (CC2) quantum chemistry calculations. Using as a reference the experimental data concerning the electronic absorption and fluorescence for the eight lowest oligofurans, we first analyzed the performance of the exchange-correlation functionals for the electronic transition energies and the reorganization energies. Subsequently, we used the best functionals alongside with the CC2 method to explore how the reorganization energies are distributed among the totally symmetric vibrations, identify the normal modes that dominate in the fine structures present in the absorption and emission bands, and trace their evolution with the increasing number of rings in the oligofuran series. Confrontation of the simulated spectra with the experiment allows for the verification of the performance of the selected DFT functionals and the CC2 method.

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Consistent Franck–Condon modeling of geometry changes for the S0→S1(ππ*) excitation in anthranilic acid: LIF spectroscopy aided by CC2 or TDDFT vibrations

Cited by 4 publications

References 47 publications

Artificial Bifunctional Photozyme of Glucose Oxidase–Peroxidase for Solar-Powered Glucose–Peroxide Detection in a Biofluid with Resorcinol–Formaldehyde Polymers

Artificial Bifunctional Photozyme of Glucose Oxidase–Peroxidase for Solar-Powered Glucose–Peroxide Detection in a Biofluid with Resorcinol–Formaldehyde Polymers

Excited-State Intramolecular Proton Transfer: A Short Introductory Review

Optical Spectra of Oligofurans: A Theoretical Approach to the Transition Energies, Reorganization Energies, and the Vibronic Activity

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