Orange-Red Fluorescent (Partially Rigidified) Donor-π-(rigidified)-Acceptor System – Computational Studies

Bhalekar, Sulochana; Bhagwat, Archana A.; Sekar, Nagaiyan

doi:10.1007/s10895-020-02506-1

Cited by 6 publications

(3 citation statements)

References 54 publications

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“…While eq accounts for the physics of the nonradiative transition rate, it does not provide useful insight for FP engineering. Reports on new fluorophores mention a dependence of the nonradiative transition rate on the S 1 –S 0 transition energy (i.e., the “energy-gap law”) which results from further theoretical development. − The classic theory of Englman and Jortner provides a framework for understanding nonradiative transition rates in terms of experimental observables such as the electronic energy gap (Δ E ), the Stokes shift (from vibrational reorganization) and vibrational frequencies . Their theory makes assumptions very similar to those of Marcus theory of electron transfer, namely that population transfer between weakly coupled initial and final states occurs by means of environmental fluctuations.…”

Section: Brightnessmentioning

confidence: 99%

Photophysical Engineering of Fluorescent Proteins: Accomplishments and Challenges of Physical Chemistry Strategies

Mukherjee

Jimenez

2022

J. Phys. Chem. B

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Fluorescent proteins (FPs) have become ubiquitous tools for biological research and concomitantly they are intriguing molecules that are amenable to study with a wide range of experimental and theoretical tools. This perspective explores the connection between the engineering of improved FPs and basic ideas from physical chemistry that explain their properties and drive the molecular design of brighter and more photostable variants. We highlight some of the progress and the many knowledge gaps in understanding the relationship between FP brightness and photostability. We also explore some of the pertinent remaining questions and suggest ways in which physical chemists might further examine the physical basis of brightness and photostability in these systems.

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Section: Brightnessmentioning

confidence: 99%

Photophysical Engineering of Fluorescent Proteins: Accomplishments and Challenges of Physical Chemistry Strategies

Mukherjee

Jimenez

2022

J. Phys. Chem. B

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“…This is a commonly used method to improve the fluorescence efficiency and intensity of coumarin compounds. [32][33][34][35] This difference between the emissive intensities of S1 and S2 may be rationalized when the theoretical calculated electron density around the methoxyl and hydroxyl functionalities, coumarin carbonyl, and corresponding triazole moiety is considered. Figure 4 shows the calculated electron density around the -C7functionalities and the corresponding electron density within the coumarin π-conjugated system and surrounding the triazole ring.…”

Section: Studies Of the Absorption And Emission Properties Of Triazolyl-coumarin Derivatives (S1) And (S2)mentioning

confidence: 99%

Synthesis and application of a fluorescent “turn-off” triazolyl-coumarin-based fluorescent chemosensor for the sensing of Fe3+ ions in aqueous solutions

Mama¹,

Battison²

2020

Arkivoc

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Two coumarin derivatives containing triazole moieties have been synthesized using "click chemistry" protocol and investigated as chemosensors for the detection of metal ions. These compounds displayed a strong preference for Fe 3+ ions with complexation resulting in fluorescent quenching. The detection limit of the preferred chemosensor was determined to be 1.4 µM. The preferred triazole-coumarin compound showed greater selectivity towards Fe 3+ in the presence of competing metal cations. Binding stoichiometry between this triazole-coumarin and Fe 3+ was shown to occur in a 1:1 ratio between the chemosensor and metal cation. The binding site of Fe 3+ to the triazole-coumarin was determined using 1 H NMR, 13 C NMR and molecular modeling studies.

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“…Recent molecular modelling studies of organic molecules illustrate their unique optical properties and confirm them to be suitable candidates for nanophotonics, terahertz photonics and optical image processing [20][21][22][23]. In this study, we investigate the molecular response of D-π-A conjugated organic dye molecules (Disperse Red 1 (DR1) and Disperse Red 73 (DR73)) using Time-Dependent Density Functional Theory (TD-DFT) and compare it with parent azobenzene structure to highlight the effect of substituents.…”

Section: Introductionmentioning

confidence: 97%

Investigating functional performance and substituent effect in modelling molecular structure, UV-visible spectra, and optical properties of D-π-A conjugated organic dye molecules: a DFT and TD-DFT study

Chanana

Batra

2021

J Mol Model

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The molecular structure, UV-Visible spectra, and optical properties of D-π-A conjugated organic dye molecules (Disperse Red 1 (DR1) and Disperse Red 73 (DR73)) were analyzed using Density Functional Theory (DFT) and Time-Dependent Density Functional Theory (TD-DFT) and compared with Azobenzene molecule to study the effect of Donor and Acceptor substituents on the molecular properties. The performance of DFT functionals is investigated using B3LYP hybrid functional and three long-range corrected functionals (CAM-B3LYP, LC-ωPBE, and ωB97XD) in conjunction with 6-31G(d,p) basis set. Using TD-DFT, we calculate the vertical excitation energies and transition dipole moment values for 100 excited states. These values were further utilized to calculate frequency dependent polarizability under Sum-Over-States (SOS) formalism and refractive index of these molecular systems. We observe that B3LYP and CAM-B3LYP perform well in estimating molecular structures while CAM-B3LYP models the UV-Visible spectra of molecules with the least error compared to experimental results. Therefore, CAM-B3LYP is reported to be the most suitable candidate for modelling disperse dye molecules. Large polarizability response is also observed for these molecules (DR1 and DR73) in comparison to parent Azobenzene structure due to charge transfer between donor and acceptor groups. For DR1 and DR73 molecules, α xx component of polarizability dominates in contrast to azobenzene where α zz dominates. The HOMO → LUMO transition during excitation contributes to the peak molecular response in simulated UV-Visible spectra. The high polarizability response of selected D-π-A conjugated molecules in comparison to parent molecule suggests that these molecules are promising candidates for tailor-made photonic and optoelectronic device development.

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Orange-Red Fluorescent (Partially Rigidified) Donor-π-(rigidified)-Acceptor System – Computational Studies

Cited by 6 publications

References 54 publications

Photophysical Engineering of Fluorescent Proteins: Accomplishments and Challenges of Physical Chemistry Strategies

Photophysical Engineering of Fluorescent Proteins: Accomplishments and Challenges of Physical Chemistry Strategies

Synthesis and application of a fluorescent “turn-off” triazolyl-coumarin-based fluorescent chemosensor for the sensing of Fe3+ ions in aqueous solutions

Investigating functional performance and substituent effect in modelling molecular structure, UV-visible spectra, and optical properties of D-π-A conjugated organic dye molecules: a DFT and TD-DFT study

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