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Effect of N-phenyl substituent on thermal, optical, electrochemical and luminescence properties of 3-aminophthalimide derivatives.

ABSTRACT: The seven N-phthalimide derivatives substituted with the amine group at the 3-C position in the phenylene ring were synthesized. The effect of N-substituent chemical structure was investigated. The thermal, electrochemical and optical studies were performed and supported by the density functional theory calculations (DFT). The electrochemical investigations of the synthesized low-molecular phthalimides revealed the one oxidation and reduction process with the HOMO energy level under - 5.81 eV and energy-band gap below 3 eV. The N-phthalimide derivatives were emitted light in a blue spectral region in solutions (in polar and non-polar) with the quantum yield between 2 and 68%, dependent on the substituent at the nitrogen atom, solvent and concentration. The N-phthalimide derivatives were emissive also in a solid state as a thin film and powder. They were tested as a component of the active layer with PVK:PBD matrix and as an independent active layer in the organic light-emitting diodes. The registered electroluminescence spectra exhibited the maximum emission band in the 469-505 nm range, confirming the possibility of using N-phthalimides with PVK:PBD matrix as the blue emitters.

SUBMITTER: Kotowicz S

PROVIDER: S-EPMC10643544 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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Effect of N-phenyl substituent on thermal, optical, electrochemical and luminescence properties of 3-aminophthalimide derivatives.

Kotowicz Sonia S Małecki Jan Grzegorz JG Cytarska Joanna J Baranowska-Łączkowska Angelika A Siwy Mariola M Łączkowski Krzysztof Z KZ Szalkowski Marcin M Maćkowski Sebastian S Schab-Balcerzak Ewa E

Scientific reports 20231113 1

The seven N-phthalimide derivatives substituted with the amine group at the 3-C position in the phenylene ring were synthesized. The effect of N-substituent chemical structure was investigated. The thermal, electrochemical and optical studies were performed and supported by the density functional theory calculations (DFT). The electrochemical investigations of the synthesized low-molecular phthalimides revealed the one oxidation and reduction process with the HOMO energy level under - 5.81 eV an ...[more]

PMID: 37957205

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Project description:We designed and synthesized unsubstituted 4,4'-bibenzo[c]thiophene 4,4'-BBT and its silyl-substituted derivatives 1,1'-Si-4,4'-BBT and 1,1',3,3'-Si-4,4'-BBT with one or two tert-butyldimethylsilyl groups on each thiophene ring, as new π-building blocks in emitters, photosensitizers and semiconductors for organic optoelectronic devices. The characterization of 4,4'-BBT, 1,1'-Si-4,4'-BBT and 1,1',3,3'-Si-4,4'-BBT was successfully determined by FTIR, 1H and 13C NMR measurements, high-resolution mass spectrometry (HRMS) analysis, photoabsorption and fluorescence spectroscopy, cyclic voltammetry (CV) and density functional theory (DFT) calculations. Moreover, a single-crystal X-ray structural analysis was successfully made for 1,1'-Si-4,4'-BBT and 1,1',3,3'-Si-4,4'-BBT. The photoabsorption and fluorescence maxima (λ abs max and λ fl max) of the three 4,4'-bibenzo[c]thiophene derivatives in toluene exhibit bathochromic shifts in the order of 4,4'-BBT (359 nm and 410 nm) < 1,1'-Si-4,4'-BBT (366 nm and 420 nm) < 1,1',3,3'-Si-4,4'-BBT (371 nm and 451 nm). The HOMO and LUMO energy levels rise in the order of 4,4'-BBT (-5.55 eV and -2.39 eV) < 1,1'-Si-4,4'-BBT (-5.45 eV and -2.34 eV) < 1,1',3,3'-Si-4,4'-BBT (-5.34 eV and -2.30 eV), but the rise of the HOMO energy level is larger than that of the LUMO energy level, resulting in the bathochromic shift of the photoabsorption band from 4,4'-BBT to 1,1',3,3'-Si-4,4'-BBT. The fluorescence quantum yields (Φ fl) of 4,4'-BBT, 1,1'-Si-4,4'-BBT and 1,1',3,3'-Si-4,4'-BBT in toluene are 0.41, 0.41 and 0.36, respectively. It is worth mentioning that in the solid state 1,1'-Si-4,4'-BBT and 1,1',3,3'-Si-4,4'-BBT show relatively high Φ fl-solid values of 0.22 and 0.25, respectively, whereas 4,4'-BBT exhibits poor solid-state fluorescence properties (Φ fl-solid < 0.02). This work provides an efficient synthetic method for the 4,4'-bibenzo[c]thiophene derivatives and their photophysical properties in the solution and solid state, electrochemical properties and X-ray crystal structures.

Dataset Information

Effect of N-phenyl substituent on thermal, optical, electrochemical and luminescence properties of 3-aminophthalimide derivatives.

Publications

Effect of N-phenyl substituent on thermal, optical, electrochemical and luminescence properties of 3-aminophthalimide derivatives.

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