2‐[(4‐Aminobutyl)ferrocenylmethylidene]‐5,6‐dimethoxy‐1‐indanone derivatives: Synthesis, characterization, and investigation of electro‐optical properties

A ferrocenyl‐based, chromophore‐containing 1‐indanone derivative was synthesized through crotonic condensation between 4‐chlorobutylferrocenecarboxaldehyde and 5,6‐dimethoxy‐1‐indanone followed by the nucleophilic substitution of chlorine atom of the obtained dyad with different aromatic and aliphat...

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Bibliographic Details
Published in:Applied organometallic chemistry 2020-06, Vol.34 (6), p.n/a
Main Authors: Rahimpour, Keshvar, Shafagh‐Azar, Ali, Abbasi, Hassan, Mohammad‐Gholizadeh, Amir, Hezarkhani, Zeinab, Teimuri‐Mofrad, Reza
Format: Article
Language:English
Subjects:
1‐indanone
Absorption spectra
Aliphatic amines
Chemical synthesis
Chemistry
Chlorine
Chromophores
crotonic condensation
Density functional theory
Diffusion rate
electroactive material
Electrochemical analysis
ferrocene
Optical properties
Quantum chemistry
Vapor phases
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Summary:A ferrocenyl‐based, chromophore‐containing 1‐indanone derivative was synthesized through crotonic condensation between 4‐chlorobutylferrocenecarboxaldehyde and 5,6‐dimethoxy‐1‐indanone followed by the nucleophilic substitution of chlorine atom of the obtained dyad with different aromatic and aliphatic amines. The electrochemical and optical properties of the synthesized compounds were investigated to explore the relationship between their structures and optical and electrochemical properties. The bandgaps determined from optical absorption spectra ranged from 2.05 to 2.15 eV. The important electrochemical parameters, including the peak potential separation, peak current ratios, and the dependence of peak currents on the scan rate, were studied. Results showed an electrochemically reversible redox system with diffusion‐controlled redox process for the synthesized compounds. The study of quantum chemistry was performed on the synthesized compounds using the density functional theory approach. The B3LYP method and 6‐311 G(d) basis set were used for optimizing the structures in the gas phase. The theoretical and experimental results show that these compounds can be considered as candidates to be used in optical applications. Synthesis of new ferrocenyl based chromophore containing1H‐inden‐1‐one core. Investigation of optical properties of these chromophoresusing Uv‐vis spectroscopy. Investigation of its electrochemical behavior via CVmethod. Electrochemically reversible redox system with diffusion controlledredox process were observed.
ISSN:0268-2605
1099-0739
DOI:10.1002/aoc.5633