Synthesis, spectroscopic investigation and computational study of 3-(1-(((methoxycarbonyl)oxy)imino)ethyl)-2H-chromen-2-one

Krishnan, Kannan Gokula; Sivakumar, R.; Thanikachalam, Venugopal; Saleem, H.; Doss, Mohan

doi:10.1016/j.saa.2015.02.021

Cited by 43 publications

(7 citation statements)

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“…The stabilization energy as well as the conjugative interactions were calculated using the second-order perturbation theory. 41 The stabilization energy E (2) associated with the delocalization from i → j for each donor ( i ) and acceptor ( j ) is determined as follows: where the donor orbital occupancy is represented by q i , the off-diagonal elements are shown by F i,j , and the diagonal NBO Fock matrix elements are represented by E i and E j . Intensive interactions between the electron donor and acceptor moieties depend on higher stabilization energy E (2) values.…”

Section: Results and Discussionmentioning

confidence: 99%

“…The stabilization energy as well as the conjugative interactions were calculated using the secondorder perturbation theory. 41 The stabilization energy E (2) associated with the delocalization from i → j for each donor (i) and acceptor (j) is determined as follows:…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Therefore, we executed an NBO analysis to evaluate the inter- and intramolecular transitions, such as hydrogen bonding, conjugative interactions, and delocalization of CC10R and CC10D1 – CC10D8 , which result in system stabilization, as tabulated in Tables S20–S28. The stabilization energy as well as the conjugative interactions were calculated using the second-order perturbation theory . The stabilization energy E (2) associated with the delocalization from i → j for each donor ( i ) and acceptor ( j ) is determined as follows: where the donor orbital occupancy is represented by q i , the off-diagonal elements are shown by F i,j , and the diagonal NBO Fock matrix elements are represented by E i and E j .…”

Section: Results and Discussionmentioning

confidence: 99%

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Influence of End-Capped Modifications in the Nonlinear Optical Amplitude of Nonfullerene-Based Chromophores with a D−π–A Architecture: A DFT/TDDFT Study

et al. 2022

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Nonlinear optical (NLO) materials have several uses in many fields such as solid physics, biology, medicine, nuclear physics, and material research. Therefore, a series of nonfullerene-based derivatives ( CC10D1 – CC10D8 ) with a D−π–A configuration was planned for the NLO investigation using CC10R as the reference molecule with structural alternations at acceptor moieties. Natural bonding orbital (NBO), UV–vis spectra, frontier molecular orbitals (FMOs), global reactivity parameters (GRPs), transition density matrix (TDM), and density of states (DOS) were analyzed using the M06/6-311G(d,p) functional in chloroform solvent to understand the NLO responses of CC10R and CC10D1 – CC10D8 . The highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) band gaps of CC10D1 – CC10D6 were illustrated to be lower than that of CC10R , with the larger bathochromic shift (726.408–782.674 nm) resulting in a significant NLO response. Along with the band gap, the FMO method also identified an efficient interfacial charge transfer from D to A moieties via a π-bridge, which was further supported by the DOS and TDM map. Moreover, NBO calculations demonstrated that extended hyperconjugation and strong internal molecular interactions were important in their stabilization. The dipole moment (μ), linear polarizability ⟨α⟩, hyperpolarizability (β total ), and second-order hyperpolarizability (γ total. ) were studied for CC10R and CC10D1 – CC10D8 . Among all of the derivatives, CC10D2 was proven to be the most appropriate candidate because of its suitable NLO behavior such as being well-supported by a reduced band gap (2.093 eV) and having a suitable maximum absorption wavelength (782.674 nm). Therefore, CC10D2 was reported to have a greater value of first hyperpolarizability (208 659.330 a.u.) compared with other derivatives and CC10R . For the second hyperpolarizability, a greater value was obtained for CC10R (5.855 × 10 7 a.u.), and its derivatives showed results comparable to that of the parent chromophore for γ total . This theoretical framework reveals that structural customization with different acceptor units plays a significant role in obtaining attractive NLO materials for optoelectronic applications.

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Section: Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

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Influence of End-Capped Modifications in the Nonlinear Optical Amplitude of Nonfullerene-Based Chromophores with a D−π–A Architecture: A DFT/TDDFT Study

et al. 2022

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“…The NBO analysis for ETPMP and TFMOS was performed by using the M06 level in combination with a 6-31G (d,p) basis set. The important parameter in this study is known as stabilization energy, which can be determined by the following eq via using second-order perturbation theory. − E false( 2 false) = q i ( F i , j ) 2 ε j − ε i Here, E (2) is the stabilization energy for the given crystal chromophore; the subscripts i and j represent donor and acceptor moieties, respectively; q i represents the donor orbital occupancy, and ε j – ε i and F i,j act for diagonal and off-diagonal NBO Fock matrix elements, respectively. The representative values for ETPMP and TFMOS are tabulated in .…”

Section: Computational Studymentioning

confidence: 99%

Synthesis, Characterizations, Hirshfeld Surface Analysis, DFT, and NLO Study of a Schiff Base Derived from Trifluoromethyl Amine

Tahir,

Ashfaq,

Munawar

et al. 2024

ACS Omega

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We synthesized an imine-based (Schiff base) crystalline organic chromophore, i.e., (E)-2-ethoxy-6-(((3-(trifluoromethyl)phenyl)imino)methyl)phenol (ETPMP), and explored its nonlinear optical (NLO) properties. The crystalline structure of ETPMP was determined by the XRD technique and equated with the associated structures utilizing a Cambridge Structural Database search. The supramolecular assembly of ETPMP was investigated regarding intermolecular interactions and short contacts by Hirshfeld surface analysis. Void analysis was performed to check the mechanical response of the crystal. Supramolecular assembly was further inspected by interaction energy calculations that were performed with the B3LYP/6-31G(d,p) functional. Besides this, the NLO properties of ETPMP and other already reported crystal TFMOS were explored utilizing the M06/6-31G(d,p) functional of the DFT approach. An excellent agreement was observed between XRD and DFT results of geometric parameters of the above-mentioned crystals. Narrow band gap along with bathochromic shift (3.489 eV and 317.225 nm, respectively) were investigated in TFMOS than that of ETPMP. Owing to these unique properties, TFMOS possesses higher linear (⟨a⟩ = 3.835 × 10 −23 esu) and nonlinear (γ tot. = 1.346 × 10 −34 esu) response as compared to ETPMP. The outcomes explicitly show the higher nonlinearity in TFMOS, highlighting its importance in potential NLO applications.

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“…Theoretically, the first-order hyperpolarizability of the title compound is of 6.38 times magnitude of urea. When it is compared to the related compounds in the literature, the calculated value of β tot of the title compound is bigger than that of 9-methoxy-2Hfuro[3,2-g]chromen-2-one (β tot = 4.8988 × 10 −30 esu calculated with B3LYP/6-311++G(d,p) method) [65] and 3-(1-(((methoxycarbonyl)oxy)imino)ethyl)-2H-chromen-2-one (β tot = 1.403 × 10 −30 esu calculated with B3LYP/6-311++G(d,p) method) [66]. These results indicate that the title compound is a good candidate of NLO material.…”

Section: Nonlinear Optical Effectsmentioning

confidence: 99%

Molecular and Electronic Analysis of (7-Chloro-2-oxo-2H-chromen-4-yl)-methyl diethylcarbamodithioate by DFT and HF Calculations

Evecen

Tanak

2019

Acta Phys. Pol. A

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The molecular geometry and vibrational frequencies of (7-chloro-2-oxo-2H-chromen-4-yl)-methyl diethylcarbamodithioate in the ground state have been calculated by using the Hartree-Fock and density functional theory methods (B3LYP and B3PW91) with 6-311++G(d,p) basis set. The results of the optimized molecular structure are presented and compared with the experimental X-ray data. The calculated vibrational frequencies are used to determine the types of molecular motions associated with each of the experimental bands observed. To investigate the nonlinear optics properties of the title compound, the polarizability and the first hyperpolarizability are calculated using the density functional B3LYP method. The predicted nonlinear optical properties of the title compound are greater than ones of urea. To determine conformational flexibility, molecular energy profile of the title compound is obtained by B3LYP calculations with respect to selected degree of torsional freedom, which is varied from −180 • to +180 • in steps of 10 •. Besides, molecular electrostatic potential, natural bond orbitals, natural atomic charges, frontier molecular orbitals, and several thermodynamic properties are performed by the density functional theory methods.

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Synthesis, spectroscopic investigation and computational study of 3-(1-(((methoxycarbonyl)oxy)imino)ethyl)-2H-chromen-2-one

Cited by 43 publications

References 50 publications

Influence of End-Capped Modifications in the Nonlinear Optical Amplitude of Nonfullerene-Based Chromophores with a D−π–A Architecture: A DFT/TDDFT Study

Influence of End-Capped Modifications in the Nonlinear Optical Amplitude of Nonfullerene-Based Chromophores with a D−π–A Architecture: A DFT/TDDFT Study

Synthesis, Characterizations, Hirshfeld Surface Analysis, DFT, and NLO Study of a Schiff Base Derived from Trifluoromethyl Amine

Molecular and Electronic Analysis of (7-Chloro-2-oxo-2H-chromen-4-yl)-methyl diethylcarbamodithioate by DFT and HF Calculations

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