Experimental and theoretical study of the spectroscopic properties and the preparation of 3-benzyl-2H-pyrano[3,2-c]chromene-2,5(6H)-dione

Moghaddam, Firouz Matloubi; Foroushani, Behzad Koushki

doi:10.1016/j.molstruc.2013.09.041

Cited by 16 publications

(4 citation statements)

References 38 publications

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“…The intensity of these bands can increase owing to conjugation or formation of hydrogen bonds [43]. Moghaddam et al [44] assigned C=O stretching absorption in the region of 1744 cm −1 to 1717 cm −1 for 3-benzyl-2H-pyrano3,2-chromene-2,5(6H)-dione. In 4-hydroxy-1-thiocoumarin, the C=O stretching was found to be present at 1701 cm −1 [43].…”

Section: C=o and C-o Vibrationsmentioning

confidence: 99%

Quantum chemical studies on the molecular structure, spectroscopic and electronic properties of (6-Methoxy-2-oxo-2H-chromen-4-yl)-methyl pyrrolidine-1-carbodithioate

Evecen

Tanak

2016

Materials Science-Poland

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In this paper, the molecular geometry, vibrational frequencies and chemical shifts of (6-Methoxy-2-oxo-2H-chromen-4-yl)methyl pyrrolidine-1-carbodithioate in the ground state have been calculated using the Hartree-Fock and density functional methods with the 6-311++G(d,p) basis set. To investigate the nonlinear optical properties of the title compound, the polarizability and the first hyperpolarizability were calculated. The conformational properties of the molecule have been determined by analyzing molecular energy properties. Using the time dependent density functional theory, electronic absorption spectra have been calculated. Frontier molecular orbitals, natural bond orbitals, natural atomic charges and thermodynamical parameters were also investigated by using the density functional theory calculations.

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Section: C=o and C-o Vibrationsmentioning

confidence: 99%

Quantum chemical studies on the molecular structure, spectroscopic and electronic properties of (6-Methoxy-2-oxo-2H-chromen-4-yl)-methyl pyrrolidine-1-carbodithioate

Evecen

Tanak

2016

Materials Science-Poland

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“…The degree of distortion from ideal tetrahedral geometry is given by the minimum and maximum coordination angles around metal ion. From Table 4 , it is clear that the bond lengths are found to be within the normal ranges obtained from the crystal structure data of few nitrogen-based derivatives like triazines (Al-Assy et al 2013 ; Azahari et al 2014 ; Bonora et al 2013 ; de-Melo et al, 2014 ; Dong et al 2014 ; Girichev et al 2010 ; Kanagathara et al 2013 ; Moghaddamand Foroushani, 2014 ; Yaremenko et al 2008 ). The obtained results are in a good agreement with the experimental results and hence strongly support them.…”

Section: Resultsmentioning

confidence: 56%

“…Whereas, for complexes 2, 3, 4 and 6, the metals are forming complexes with one Atr through the N of ring and N of less bulky chain including Cl and H 2 O as additional ligands to stabilize the metal complexes. The cis angles around the metal ions are variable, range from 74.17 o to 99.34 o , respectively; the trans angles ranging from 130.26 o to 162.53 o , respectively, indicating octahedral to square planar geometry with tetrahedral distortion (Al-Assy et al 2013 ; Azahari et al 2014 ; Bonora et al 2013 ; de-Melo et al 2014 ; Dong et al 2014 ; Girichev et al 2010 ; Kanagathara et al 2013 ; Moghaddamand Foroushani, 2014 ; Yaremenko et al 2008 ). For all complexes, the dihedral coordination around the metal center, involving O, N and Cl atoms is distorted.…”

Section: Resultsmentioning

confidence: 99%

Interactions of atrazine with transition metal ions in aqueous media: experimental and computational approach

Kumar

Upadhyay

et al. 2015

3 Biotech

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Transition metal ions have their own significances and utility. Externally applied pesticides may alter the bioavailability of these metal ions to plants through the coordinating ability of these pesticides with metal ions. In current study a series of metal complexes containing atrazine (Atr) group(s) attached to metal(II) (M) frame, with the formula; [M(Atr)n.xH2O.yCl] (where M = Mn, Fe, Co, Ni, Cu or Zn; n = 1 or 2; x = 1–4; y = 1–2), have been synthesized for the first time to check the interactions of atrazine with transition metal ions. More importantly, all the complexes were synthesized at neutral pH in aqueous medium. The major differences among the FTIR spectra were observed between 3,700–2,800 and 1,800–1,350 cm−1. On the basis of FTIR, CHN and computational study, it was observed that Mn, Ni and Cu formed complexes in 1:2 and Fe, Co and Zn in 1:1. The obtained results were supported by 3D molecular modeling using GAMESS computations as a package of ChemBio3D Ultra14 program. The FTIR spectral analysis and 3D molecular modeling suggests that the Atr can show coordination through the nitrogen (in between two side chains) of ring as well as nitrogen (non steric amine) of side chain with different metal ions.

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“…For instance, F. M. Moghaddam et al 20 reported, synthesis of 3-benzyl-2H-pyrano [3,2c]chromene-2,5(6H)-dione via tandem reaction of 4-hydroxycoumarin with Baylis-Hillman adduct acetate under Et 3 N and studied the experimental and theoretical spectroscopic properties. 21 Therefore, there is no systematic spectroscopic study of coumarine derivatives are available in literature to the best of our knowledge.…”

Section: Introductionmentioning

confidence: 99%

2H-Pyrano[3,2-c]chromene-2,5(6H)-diones: Synthesis, Characterization, Photophysical and Redox Studies for Potential Optoelectronic Applications

et al. 2022

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Herein, we report the preparation of 2H-pyrano[3,2-c]chromene-2,5(6H)-diones 3a-x by reacting 4hydroxycoumarins 1a-b with Baylis-Hillman adducts 2a-w having electron releasing or electron withdrawing groups on benzyl ring of the pyranochromene moiety and study of their photophysical properties. The study of optical and electrochemical properties of the prepared compounds reveals that the electron releasing and electron withdrawing groups has not much impact on ground and excited state electronic behavior on pyranochromene moiety. The density functional theory suggests the highest occupied molecular orbital and lowest unoccupied molecular orbitals spread on coumarin moiety of pyranochromene unit. Further, these compounds are thermally stable (up to 200 o C) and lead to blue or green emission that should facilitate the development of organic light emitting diodes (OLEDs).

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Experimental and theoretical study of the spectroscopic properties and the preparation of 3-benzyl-2H-pyrano[3,2-c]chromene-2,5(6H)-dione

Cited by 16 publications

References 38 publications

Quantum chemical studies on the molecular structure, spectroscopic and electronic properties of (6-Methoxy-2-oxo-2H-chromen-4-yl)-methyl pyrrolidine-1-carbodithioate

Quantum chemical studies on the molecular structure, spectroscopic and electronic properties of (6-Methoxy-2-oxo-2H-chromen-4-yl)-methyl pyrrolidine-1-carbodithioate

Interactions of atrazine with transition metal ions in aqueous media: experimental and computational approach

2H-Pyrano[3,2-c]chromene-2,5(6H)-diones: Synthesis, Characterization, Photophysical and Redox Studies for Potential Optoelectronic Applications

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