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2‐[(4‐Aminobutyl)ferrocenylmethylidene]‐5,6‐dimethoxy‐1‐indanone derivatives: Synthesis, characterization, and investigation of electro‐optical properties
Author(s) -
Rahimpour Keshvar,
ShafaghAzar Ali,
Abbasi Hassan,
MohammadGholizadeh Amir,
Hezarkhani Zeinab,
TeimuriMofrad Reza
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5633
Subject(s) - chemistry , electrochemistry , redox , nucleophilic substitution , chromophore , density functional theory , condensation , absorption spectroscopy , diffusion , nucleophile , photochemistry , computational chemistry , organic chemistry , electrode , catalysis , thermodynamics , physics , quantum mechanics
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.