A thiophene-based bisazomethine and its inclusion complex with permethylated β-cyclodextrin: Exploring structural characteristics and computational chemistry models

Resmerita, Ana-Maria; Cojocaru, Corneliu; Damaceanu, Mariana-Dana; Balan-Porcarasu, Mihaela; Shova, Sergiu; El Haitami, Alae; Farcas, Aurica

doi:10.1016/j.dyepig.2024.112472

Dyes and Pigments

2025

DOI: 10.1016/j.dyepig.2024.112472

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A thiophene-based bisazomethine and its inclusion complex with permethylated β-cyclodextrin: Exploring structural characteristics and computational chemistry models

Ana-Maria Resmerita,

Corneliu Cojocaru,

Mariana-Dana Damaceanu

et al.

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Aromatic Co-Polyazomethine Polyrotaxane with Enhanced Solubility Applied as a Hole Carrier in a p–n Heterojunction Diode

Ursu,

Resmerita,

Tigoianu

et al. 2024

ACS Appl. Polym. Mater.

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Conjugated coazomethine 4 and the polyrotaxane 4•TMe-βCD were synthesized by Suzuki coupling of bromine-terminated bis-azomethine 1 and its encapsulated form 1•TMe-βCD with 9,9-dioctylfluorene-2,7-diboronic acid bis(1,3-propanediol) ester 2, followed by the end-capping with 3-bromothiophene 3. FT-IR and 1 H NMR spectroscopies proved the chemical structures of 4 and 4•TMe-βCD. Polyrotaxane formation improves solubility, film-forming ability, adhesivity onto different substrates, and thermal stability. The result of 2,3,6-tri-O-methyl-βcyclodextrin (TMe-βCD) encapsulation was evidenced by higher fluorescence (Φ FL ), phosphorescence (Φ Ph ), lifetime (τ), reversible electrochemical reduction, or better selforganization of 4•TMe-βCD. Doping of 4 and 4•TMe-βCD by exposure to iodine was found to increase the electrical conductivities up to 1 × 10 −7 S•cm −1 . Owing to 4•TMe-βCD has better photophysical properties, the hole-transporting capability was explored for the first time in a hybrid p−n heterojunction diode. The measured current−voltage characteristics of the eGaIn/4• TMe-βCD/ZnO/Al/ZnO diode revealed a rectification ratio of 56 at ±3 V and saturation current of 0.46 mA, highlighting the ambipolar characteristics of 4•TMe-βCD, which poses both p-and n-type doping features. These findings are relevant for a better understanding of the hole-transporting ability of supramolecular semiconductor materials with a wide range of applications in optoelectronics.

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Aromatic Co-Polyazomethine Polyrotaxane with Enhanced Solubility Applied as a Hole Carrier in a p–n Heterojunction Diode

Ursu,

Resmerita,

Tigoianu

et al. 2024

ACS Appl. Polym. Mater.

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show abstract

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A thiophene-based bisazomethine and its inclusion complex with permethylated β-cyclodextrin: Exploring structural characteristics and computational chemistry models

Cited by 1 publication

References 33 publications

Aromatic Co-Polyazomethine Polyrotaxane with Enhanced Solubility Applied as a Hole Carrier in a p–n Heterojunction Diode

Aromatic Co-Polyazomethine Polyrotaxane with Enhanced Solubility Applied as a Hole Carrier in a p–n Heterojunction Diode

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