Novel π-extended polycyclic chromenopyridines: Synthesis, DFT, electrochemical, and thermogravimetric evaluation

[Display omitted] •Novel π-extended polycyclic chromenopyridines were synthesized via cascade reaction of 3-cyanochromone with different active methylene reagents.•The DFT and electrochemical evaluations revealed a decreased energy gap of chromenopyridine derivatives compared to 3-cyanochromone prec...

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Published in:Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2023-01, Vol.434, p.114222, Article 114222
Main Authors: El-Sawi, Aya Atef, Hassan Habib, Ibrahim, Elmorsy, Mohamed Ramadan, Ullah, Asmat, El-Attar, Rehab Omar, Abdel-Rahman, Abdel-Rahman Hassan, El-Desoky, El-Sayed Ibrahim, Ahmed Abozeid, Mohamed
Format: Article
Language:English
Subjects:
Chromenopyridine, DFT
Cyclic voltammetry
LUMO
Organic electronics
Polycyclic aromatic hydrocarbons (PAHs)
Thermogravimetry, HOMO
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Summary:[Display omitted] •Novel π-extended polycyclic chromenopyridines were synthesized via cascade reaction of 3-cyanochromone with different active methylene reagents.•The DFT and electrochemical evaluations revealed a decreased energy gap of chromenopyridine derivatives compared to 3-cyanochromone precursor.•Thermogravimetric analysis showed high thermal stabilities of chromenopyridines.•The synthesized chromenopyridine would be a promising scaffold for different organic electronic applications. Polycyclic aromatic hydrocarbons (PAHs) doped with heteroatoms such as thiophene, carbazole, and boron-dipyrromethene (BODIPY) have attracted increased attention because of their excellent optoelectronic properties in addition to the robust skeletons required for the construction of efficient organic electronics. Herein, novel π-extended polycyclic chromenopyridines 3a-d, 5, and 7 were synthesized via base-catalyzed cascade reaction of 3-cyano-7,8-benzochromone 1 with acetonitrile derivatives 2a-d, ethyl chloroacetate 4, and phenylpyrazolone 6 in very good to excellent yields. Density functional theory (DFT) calculation and electrochemical evaluation of compounds 3a-d, 5, and 7 revealed a decreased energy gap (Eg) compared to the precursor 3-cyanochromone 1 indicating their superior semiconducting and light-harvesting abilities. In addition, the observed thermal stability of chromenopyridines 3a-d, 5, and 7 with maximum weight loss at temperatures between 301.72 and 557.28 °C qualified them for wide organic electronic applications.
ISSN:1010-6030
1873-2666
DOI:10.1016/j.jphotochem.2022.114222