Synthesis, crystal structure and electronic applications of monocarboxylic acid substituted phthalonitrile derivatives combined with DFT studies

Tunç, Gülenay; Canımkurbey, Betül; Dedeoglu, Burcu; Zorlu, Yunus; Eryılmaz, Serpil; Gürek, Ayşe Gül

doi:10.1016/j.molstruc.2021.130545

Cited by 6 publications

(2 citation statements)

References 60 publications

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“…The hydrolysis of succinimide under alkaline conditions and subsequent lactonization afforded carboxylic acid 12 [22] . Amide trans ‐ 13 was obtained by changing the nucleophile in the ring‐opening reaction to ammonium hydroxide [23] . These methods may be useful for not only accessing various chiral building blocks but also accelerating the manufacture of various biologically active substances.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective and Chemoselective Phosphine Oxide‐catalyzed Aldol Reactions of N‐Unprotected Cyclic Carboxyimides

Yoshiwara

Kotani

Nakajima

2023

Chemistry A European J

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Asymmetric catalytic transformations of N-unprotected cyclic carboxyimides such as succinimides, hydantoins, oxazolidinediones, and glitazones, is a powerful way of directly accessing variety of biologically valuable chiral compounds. Herein, a bis(trichlorosilyl) nucleophilic intermediate formed from cyclic carboxyimides was reacted with aldehydes via (S)-SEGPHOS dioxide (SEGPHOSO), proceeding the aldol reaction in highly enantioselective fashion through a cyclic transition state. Furthermore, N-unprotected carboxyimides were chemoselectively activated, even in the presence of N-alkylated carboxyimides, to undergo stereoselective and chemoselective aldol reactions via in situ silicon tetrachloride activation. The functionalized cyclic carboxyimides is readily derived to the several synthetic units derivatization to various chiral building blocks without unnecessary protection/deprotection steps.

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Section: Resultsmentioning

confidence: 99%

Enantioselective and Chemoselective Phosphine Oxide‐catalyzed Aldol Reactions of N‐Unprotected Cyclic Carboxyimides

Yoshiwara

Kotani

Nakajima

2023

Chemistry A European J

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“…In physics, chemistry, and materials science, density functional theory (DFT) is a computational quantum mechanical modeling tool used to examine the electronic structure (or nuclear structure) of atoms, molecules, and dense phases in a variety of ways [9]. With advances in technique and applications, it is now possible to acquire high-quality predicted attributes such as lattice constants, cohesion/absorption energies, band structures, surface reactivity, thermochemistry, rate constants, and other physical and chemical parameters [10,11]. As a result, the microscopic mechanism can be analyzed by constructing interaction models between different components.…”

Section: Introductionmentioning

confidence: 99%

DFT Calculations and Molecular Docking Study in 6-(2”-Pyrrolidinone-5”-Yl)-(-) Epicatechin Molecule From Flavonoids

BAĞLAN>

Yıldıko

GÖREN>

2023

Eskişehir Teknik Üniversitesi Bilim Ve Teknoloji Dergisi B - Teorik Bilimler

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The 6-311G(d,p) and SDD basis sets have been used to calculate the vibration frequencies, and the DFT/B3LYP approach was used to optimize the structure. The energy gap of the molecule has been calculated using the lowest unoccupied molecular orbital (LUMO) with the highest occupied molecular orbital (HOMO). The stability and charge delocalization of the Title molecule have been investigated using natural bond orbital (NBO) analysis. The dipole moment, polarizability, and first-order hyperpolarizability, as well as the molecular electrostatic potentially (MEP) and thermodynamic features, have been used to compute the nonlinear optical (NLO) behavior of the title molecule. The Schrödinger program was used to conduct molecular docking works to determine information about the interactions between the AChE and BChE enzymes and the chemical. In addition, a molecular docking study was analyzed for compounds PEP with AChE and BChE synthase binding protenins (PDB:4M0E) and (PDB:6SAM) using the Discovery Studio 2021 Client program. Compound AChE showed -7.105 kcal/mol while compounds BChE showed a inding score of -7.784 kcal/mol.

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Cosensitization of a Tetraethylene Glycol‐Substituted Unsymmetrical Zinc Phthalocyanine Sensitized Solar Cells with D131 Auxiliary Dye Exhibited Enhanced Efficiency

Kute,

Ketkar,

Jagushte

et al. 2024

ChemistrySelect

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An asymmetric zinc phthalocyanine dye (ZnPcT3C), bearing three tetraethylene glycol donor groups and one carboxylic acid anchoring group, was synthesized as a photosensitizer dye for dye‐sensitized solar cells (DSSCs). The tetraethylene glycol (TEG), consisting of four ethoxy units, works as an amphiphilic long‐chain donor group that greatly helped in reducing the molecular aggregation. Carboxylic acid group, on the other hand, an acceptor, together with TEG in ZnPcT3C functions as a ‘push–pullʼ system suitable for DSSCs. Absorption spectra of ZnPcT3C in DMSO showed a strong sharp Q band in the infrared region 600–700 nm with (λmax = 682 nm) and a less intense soret band appeared in the region 300–400 nm with λmax = 340 nm. The zinc phthalocyanine (ZnPcT3C) exhibited molar extinction coefficient (ε) of 72,727 L mol−1cm−1. The emission was observed at λem = 695 nm upon excitation at 650 nm and exhibited a fluorescence decay of 2.82 ns. The ZnPcT3C dye sensitised solar cell (c = 1 mM) exhibited the power conversion efficiency (η) of 3.52% in chloroform in I−/I3 electrolyte under simulated 100% brightness. Cosensitization of ZnPcT3C with another auxiliary dye D131 in 1:1 ratio in a cocktail‐type DSSC attained the power conversion efficiency of twice as high as η = 6.27% in an identical condition. A mixture of D131 (λmax = 470 nm) dye with the ZnPcT3C phthalocyanine harvests sunlight across the visible spectra, enabling DSSCs to attain a large photocurrent and photovoltage, enhancing power conversion efficiency.

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Synthesis, crystal structure and electronic applications of monocarboxylic acid substituted phthalonitrile derivatives combined with DFT studies

Cited by 6 publications

References 60 publications

Enantioselective and Chemoselective Phosphine Oxide‐catalyzed Aldol Reactions of N‐Unprotected Cyclic Carboxyimides

Enantioselective and Chemoselective Phosphine Oxide‐catalyzed Aldol Reactions of N‐Unprotected Cyclic Carboxyimides

DFT Calculations and Molecular Docking Study in 6-(2”-Pyrrolidinone-5”-Yl)-(-) Epicatechin Molecule From Flavonoids

Cosensitization of a Tetraethylene Glycol‐Substituted Unsymmetrical Zinc Phthalocyanine Sensitized Solar Cells with D131 Auxiliary Dye Exhibited Enhanced Efficiency

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