Phenothiazine-based dyes containing imidazole with π-linkers of benzene, furan and thiophene: Synthesis, photophysical, electrochemical and computational investigation

Nhari, Laila M.; El‐Shishtawy, Reda M.; Bouzzine, Si Mohamed; Hamidi, Mohamed; Asiri, Abdullah M.

doi:10.1016/j.molstruc.2021.131959

Cited by 26 publications

(9 citation statements)

References 68 publications

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“…A general framework based on a donor–acceptor system with π-spacers (D−π–A) induces intermolecular charge transfer (ICT) and determines the physicochemical properties of the device’s absorbing layer. − Therefore, designing an appropriate structure is significant for developing efficient and stable DSSCs. Heteroaromatic units such as triphenylamine, − carbazole, − phenoxazine, − phenothiazine, − and imidazole − are successfully used as electron-donating groups in D−π–A compounds. Especially interesting as donor blocks for dyes is the nonplanar phenothiazine conformation, which may inhibit molecular aggregation, lowering PV performance in DSSCs.…”

Section: Introductionmentioning

confidence: 99%

New D−π–D−π–A Systems Based on Phenothiazine Derivatives with Imidazole Structures for Photovoltaics

et al. 2022

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Two new compounds with an N-octyl phenothiazine core substituted at C(7) position via a triple bond with imidazole-containing butyl or dodecyl chains bearing on the opposite side at the C(7) cyanoacrylate moiety were synthesized. Photophysical and electrochemical studies were performed to evaluate the possibility of applying them in the dye-sensitized solar cells (DSSCs). The investigations were supported by density functional theory and time-dependent DFT. The synthesized dyes showed a similar absorption profile ranging from 250 to 600 nm in solvents and a high value of light-harvesting efficiency of about 0.8. It was found that its photoluminescence quantum yield was solvent-dependent, and the highest value (about 50%) was reached in DMF solution. Electrochemical measurements revealed that both compounds showed electron injection ability from the LUMO of the molecule to the TiO 2 conduction band and the possibility of regeneration by an electrolyte. DSSCs sensitized with the phenothiazine derivatives differing in TiO 2 thickness and the type of electrolyte (iodide and cobalt) were prepared. Additionally, transient absorption measurements in solution and solar cells were carried out to study excited-state properties and electron transfer dynamics. The influence of the hydrophobic hydrocarbon chain length of the imidazole unit in these dyes as well as TiO 2 thickness and the type of electrolyte on the device performance was observed. DSSCs sensitized with phenothiazine with dodecyl chains showed higher photocurrent, open-circuit voltage, and finally the power conversion efficiency, regardless of TiO 2 thickness.

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Section: Introductionmentioning

confidence: 99%

New D−π–D−π–A Systems Based on Phenothiazine Derivatives with Imidazole Structures for Photovoltaics

et al. 2022

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“…[61] On the one hand, compound 4 showed red-shifted absorption spectra compared to compound 2, probably owing to extensive conjugation of thienyl group compared to phenyl group. [62][63] In addition, the band gap energy (E gap ) could be calculated from the onset of the absorption spectra, which were estimated as 3.18 eV, 2.97 eV, 3.10 eV, and 2.89 eV for compounds 1-4, respectively. The coplanar structures of C=C moieties are in accordance with the smaller optical band gaps of compounds 2 and 4.…”

Section: Thermal Optical and Electrochemical Propertiesmentioning

confidence: 99%

Development and Characterization of Solution‐Processable Dithieno[3,2‐b : 2’,3’‐d]thiophenes Derivatives with Various End‐capped Groups for Organic Field‐Effect Transistors

Kang

Jang

et al. 2022

ChemPlusChem

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In this paper, four organic materials based on dithieno[3,2b : 2',3'-d]thiophene (DTT) core structure with end-capping groups (phenyl and thienyl) and linker (acetylenic and olefinic) between DTT-core and end-capping groups were synthesized and characterized as solution-processable organic semiconductors (OSCs) for organic field-effect transistors (OFETs). Thermal, optical, and electrochemical properties of the corresponding materials were determined. Next, all DTT-derivatives were coated by solution-shearing method, and the thin-film microstructures and morphologies were investigated. To investigate the electrical performance of four newly synthesized DTTderivatives, bottom-gate/top-contact OFETs were fabricated and characterized in ambient condition. It was found that substitution of acetylenic for olefinic linkers between DTT-cores and end-capping groups enhanced device performance. Especially, the resulting OFETs based on the compound containing phenylacetylene exhibited the highest hole mobility of 0.15 cm 2 /Vs and current on/off ratio of ~10 6 , consistent with film morphology and texture showing long range interconnected crystalline grains and strong diffraction peaks.

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“…56 Signicantly, substituted imidazole derivatives have been of major interest in the production of novel materials for optoelectronic applications. 35 Also, small organic molecules with a highly substituted imidazole moiety as an electron donor with different acceptors have scarcely been published. 57 The majority of the newly produced mechanouorochromic (MFC) materials as ICT dyes with AIEactive features, together with their simple synthetic techniques, have revealed that small organic molecules as AIEactive materials are preferred over large structures.…”

Section: Introductionmentioning

confidence: 99%

“…Significantly, substituted imidazole derivatives have been of major interest in the production of novel materials for optoelectronic applications. 35 Also, small organic molecules with a highly substituted imidazole moiety as an electron donor with different acceptors have scarcely been published. 57 …”

Section: Introductionmentioning

confidence: 99%

“…32 Organic D-p-A systems have remarkable optical and spectral properties due to their highly polarizable structures resulting from efficient ICT from the donor to the acceptor. [33][34][35][36][37][38] Consequently, ICT compounds have been earned substantial research interest owing to their potential application in chemical sensing, [39][40][41][42] nonlinear optical (NLO) materials, [43][44][45][46] optoelectronic devices, 47 dye-sensitized solar cells, [48][49][50][51][52][53] and organic light-emitting diodes (OLEDs) 54,55 with large Stokes shi and dipole moment in the excited state. 56 Signicantly, substituted imidazole derivatives have been of major interest in the production of novel materials for optoelectronic applications.…”

Section: Introductionmentioning

confidence: 99%

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AIE and reversible mechanofluorochromism characteristics of new imidazole-based donor–π–acceptor dyes

et al. 2022

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Phenothiazine-based dyes containing imidazole with π-linkers of benzene, furan and thiophene: Synthesis, photophysical, electrochemical and computational investigation

Cited by 26 publications

References 68 publications

New D−π–D−π–A Systems Based on Phenothiazine Derivatives with Imidazole Structures for Photovoltaics

New D−π–D−π–A Systems Based on Phenothiazine Derivatives with Imidazole Structures for Photovoltaics

Development and Characterization of Solution‐Processable Dithieno[3,2‐b : 2’,3’‐d]thiophenes Derivatives with Various End‐capped Groups for Organic Field‐Effect Transistors

AIE and reversible mechanofluorochromism characteristics of new imidazole-based donor–π–acceptor dyes

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