Synthesis, spectroscopic, SC-XRD/DFT and non-linear optical (NLO) properties of chromene derivatives

Arif, Noor; Shafiq, Zahid; Noureen, Sajida; Khalid, Muhammad; Ashraf, Asfa; Yaqub, Muhammad; Irshad, Shabana; Khan, Muhammad Usman; Arshad, Muhammad Nadeem; Braga, Ataualpa Albert Carmo; Ragab, Ahmed H.; Al-Mhyawi, Saedah R.

doi:10.1039/d2ra07134g

Cited by 6 publications

(3 citation statements)

References 78 publications

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“…FMO analysis is an effective way to investigate electronic transitions, chemical stability, and reactivity of a molecule. − The HOMO (highest occupied molecular orbital) and the LUMO (lowest unoccupied molecular orbital) of a system have a significant impact on the optical and electrical properties of molecules by using the HOMO–LUMO band gap. − LUMO expresses the capacity to accept electrons, whereas HOMO depicts the potential to donate electrons. , Molecules showing large ICT usually offer the best NLO response. , …”

Section: Resultsmentioning

confidence: 99%

Quantum Chemical Exploration of A−π₁–D₁–π₂–D₂-Type Compounds for the Exploration of Chemical Reactivity, Optoelectronic, and Third-order Nonlinear Optical Properties

Mustafa,

Shafiq,

Shaikh

et al. 2023

ACS Omega

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Organic compounds exhibit significant nonlinear optical (NLO) properties and can be utilized in various areas like optical parameters, fiber optics, and optical communication. Herein, a series of chromophores (DBTD1–DBTD6) with an A−π1–D1–π2–D2 framework was derived from a prepared compound (DBTR) by varying the structure of π-spacer and terminal acceptor. The DBTR and its investigated compounds were optimized at the M06/6-311G(d,p) level of theory. Frontier molecular orbitals (FMOs), nonlinear optical (NLO) properties, global reactivity parameters (GRPs), natural bonding orbital (NBO), transition density matrix (TDM), molecular electrostatic potential (MEP), and natural population analysis (NPA) were accomplished at the abovementioned level to describe the NLO findings. DBTD6 has the lowermost band gap (2.131 eV) among all of the derived compounds. The decreasing order of highest occupied molecular orbital–lowest unoccupied molecular orbital (HOMO–LUMO) energy gap values was DBTR > DBTD1 > DBTD2 > DBTD3 > DBTD4 > DBTD5 > DBTD6. The NBO analysis was carried out to describe noncovalent interactions such as conjugative interactions and electron delocalization. From all of the examined substances, DBTD5 showed the highest λmax value at 593.425 nm (in the gaseous phase) and 630.578 nm (in chloroform solvent). Moreover, the βtot and ⟨γ⟩ amplitudes of DBTD5 were noticed to be relatively greater at 1.140 × 10–27 and 1.331 × 10–32 esu, respectively. So, these outcomes disclosed that DBTD5 depicted the highest linear and nonlinear properties in comparison to the other designed compounds, which underlines that it could make a significant contribution to hi-tech NLO devices.

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Section: Resultsmentioning

confidence: 99%

Quantum Chemical Exploration of A−π₁–D₁–π₂–D₂-Type Compounds for the Exploration of Chemical Reactivity, Optoelectronic, and Third-order Nonlinear Optical Properties

Mustafa,

Shafiq,

Shaikh

et al. 2023

ACS Omega

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“…NBO calculations indicate that the host/guest complex is stabilized through interactions among the carbon molecules and the transfer of charge between occupied and unoccupied orbitals within the complex. Notably, the highest hyperconjugative E (2) energy is observed during these intermolecular interactions, underscoring their significance in potential medicinal and biological applications [33]…”

Section: Nbo Analysismentioning

confidence: 99%

A Quantum Chemical Investigation on Structural, Spectroscopic and Nonlinear Optical properties of an Organic Molecule Serotonin

et al. 2024

Int. Res. J. multidiscip. Technovation

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Serotonin, a neurotransmitter known for promoting feelings of happiness and optimism, was the subject of theoretical studies conducted using Gaussian software. In these experiments, the 6-311++G/B3LYP basis set was employed. The finite-field-based B3LYP/6-311++G (d,p) approach was used to compute the first-order hyper polarizability and associated properties of this chemical system. Additionally, a Natural Bond Orbital (NBO) analysis was conducted to assess the molecule's stability, taking into account hyper conjugative interactions and charge delocalization. Additionally, HOMO-LUMO energy levels were computed to assess whether a chemical exhibits electrophilic or nucleophilic characteristic. TD-DFT simulations were conducted to examine the electrical and optical characteristics of the material, including absorption wavelengths and excitation energy. Subsequently, the chemical compound's electrophilic or nucleophilic nature was determined by calculating the molecular electrostatic potential (MEP).

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“…Pyrimidine fused quinoline derivatives have a wide range of medicinal properties, including antibacterial, antifungal, anticancer, analgesic, antimalarial, antitumor, anti-inflammatory, antiviral, and antioxidant effects 17 – 19 . Also, chromene derivatives have diverse pharmacological properties, such as anticancer 20 , antimicrobials 21 , antivirals 22 , anticoagulants 23 , and anti-inflammatory activities 24 . Therefore, it is crucial for the pharmaceutical industry to develop synthetic methods for chromene derivatives.…”

Section: Introductionmentioning

confidence: 99%

Advances in the greener synthesis of chromopyrimidine derivatives by a multicomponent tandem oxidation process

Ghamari Kargar,

Bagherzade

2023

Sci Rep

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A hydrophilic cobalt/copper heterogeneous bimetallic catalyst named mTEG-CS-Co/Cu-Schiff-base/IL was successfully synthesized from chitosan polysaccharide. The new catalyst was investigated and confirmed using various techniques including FT-IR, FE-SEM, EDX-EDS, XRD, TEM, TGA, AFM, NMR and ICP. The catalyst exhibited powerful catalyst activity for the tandem one pot oxidative chromopyrimidine reaction from benzyl alcohols under mild conditions, utilizing air as a clean source in a green protocol. The catalyst was compatible with a wide range of benzyl alcohols, and aldehydes formed in situ, and bis-aldehydes synthesized were condensed with urea/4‑hydroxycumarin to provide favorable products in good yields for all derivatives (14 new derivatives). The presence of tri-ethylene glycol and imidazolium moieties with hydrophilic properties on the mTEG-CS-Co/Cu-Schiff-base/IL nanohybrid provides dispersion of the nanohybrid particles in water, leading to higher catalytic performance. Furthermore, the reaction exhibited several other notable features, including low catalyst loading, the ability to be recycled for up to 6 stages, high atom economy, a simple work procedure, short reaction time, utilization of an environmentally friendly nanohybrid, and the replacement of volatile and organic solvents with water solvent.

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Synthesis, spectroscopic, SC-XRD/DFT and non-linear optical (NLO) properties of chromene derivatives

Abstract: Efficient synthesis of novel coumarin-based pyrano-chromene derivatives.

Cited by 6 publications

References 78 publications

Quantum Chemical Exploration of A−π₁–D₁–π₂–D₂-Type Compounds for the Exploration of Chemical Reactivity, Optoelectronic, and Third-order Nonlinear Optical Properties

Quantum Chemical Exploration of A−π₁–D₁–π₂–D₂-Type Compounds for the Exploration of Chemical Reactivity, Optoelectronic, and Third-order Nonlinear Optical Properties

A Quantum Chemical Investigation on Structural, Spectroscopic and Nonlinear Optical properties of an Organic Molecule Serotonin

Advances in the greener synthesis of chromopyrimidine derivatives by a multicomponent tandem oxidation process

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Synthesis, spectroscopic, SC-XRD/DFT and non-linear optical (NLO) properties of chromene derivatives

Abstract: Efficient synthesis of novel coumarin-based pyrano-chromene derivatives.

Cited by 6 publications

References 78 publications

Quantum Chemical Exploration of A−π1–D1–π2–D2-Type Compounds for the Exploration of Chemical Reactivity, Optoelectronic, and Third-order Nonlinear Optical Properties

Quantum Chemical Exploration of A−π1–D1–π2–D2-Type Compounds for the Exploration of Chemical Reactivity, Optoelectronic, and Third-order Nonlinear Optical Properties

A Quantum Chemical Investigation on Structural, Spectroscopic and Nonlinear Optical properties of an Organic Molecule Serotonin

Advances in the greener synthesis of chromopyrimidine derivatives by a multicomponent tandem oxidation process

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Quantum Chemical Exploration of A−π₁–D₁–π₂–D₂-Type Compounds for the Exploration of Chemical Reactivity, Optoelectronic, and Third-order Nonlinear Optical Properties

Quantum Chemical Exploration of A−π₁–D₁–π₂–D₂-Type Compounds for the Exploration of Chemical Reactivity, Optoelectronic, and Third-order Nonlinear Optical Properties