Electronic properties of carbazole/biphenylamino functionalized sulfone‐based host materials

Xu, Xiaopei; Huang, Zehua; Liang, Xuefeng; Tang, Xinyuan; Zhao, Yongze; Li, Huifang; He, Ya‐Ling; Zhang, Lisheng

doi:10.1002/poc.4484

Cited by 4 publications

(1 citation statement)

References 51 publications

(63 reference statements)

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“…Carbazoles are N-heterocyclic aromatic compounds that exhibit excellent fluorescence properties and form an important structural element of many compounds used for the manufacture of electronic materials, polymers, or dyes. 1–3 These compounds have high biological and pharmacological activities including anticancer, antimicrobial, antiviral, anti-inflammatory, and antioxidant activities. 4–9 In the literature, some carbazole derivatives have been considered potent anticancer agents owing to their high antiproliferative activities against various cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

Design of N-heterocycle based-phthalonitrile/metal phthalocyanine–silver nanoconjugates for cancer therapies

Öney,

Yenilmez,

Bahar

et al. 2023

Dalton Trans.

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Section: Introductionmentioning

confidence: 99%

Design of N-heterocycle based-phthalonitrile/metal phthalocyanine–silver nanoconjugates for cancer therapies

Öney,

Yenilmez,

Bahar

et al. 2023

Dalton Trans.

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Exploring the Impact of Carbazole Position on Thermally Activated Delayed Fluorescence and Room-Temperature Phosphorescence Properties in Phthalimide–Carbazole Conjugates: A Density-Functional Theory Study

Panaha,

Saini,

Thomas

2024

J. Phys. Chem. C

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Aromatic imide-based thermally activated delayed fluorescence (TADF) emitters have become increasingly popular due to their unique properties such as rigid structures, pronounced thermal stability, strong electron-withdrawing ability, and exceptional photoluminescence characteristics. In this work, the phthalimide unit is integrated with the carbazole donor in different molecular designs (D-π-A, π-A-D, π-A-D 2 , and D-π-A-D) and their TADF and room-temperature phosphorescence (RTP) properties are theoretically investigated. Descriptors such as the energy gap between singlet and triplet excited states (ΔE ST ), spin orbit coupling (SOC), charge transfer (CT) indices, and rate constants of excited state processes were analyzed to study the nature of the excited state. The D-π-A and D-π-A-D molecules possess small ΔE ST , CT-dominated S 1 and T 1 states, relatively low SOC values, and high radiative and reverse intersystem crossing (RISC) rates, while the π-A-D and π-A-D 2 molecules with direct substitution of carbazole on phthalimide core showed large ΔE ST , CT-dominated S 1 state, hybridized and local charge transfer T 1 state, large SOC, high intersystem crossing, and low RISC rates. Careful analysis of energy-level diagram and hole−electron distribution revealed the role of the closely lying T 2 state with the S 1 state in fast upconversion of triplet excitons through a multichannel RISC process in π-A-D 2 -and D-π-A-D-based molecules. Overall, the D-π-A and D-π-A-D molecules possess parameters indicative of TADF emission, and the π-A-D and π-A-D 2 molecules inherit parameters facilitating RTP emission. Additionally, the π-A-D 2 molecules can display TADF emission; on the contrary, the π-A-D molecules display poor TADF propensity.

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Emission in the Biological Window from AIE-Based Carbazole-Substituted Furan-Based Compounds for Organic Light-Emitting Diodes and Random Lasers

Lupinska,

Kotowicz,

Grabarz

et al. 2024

ACS Omega

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The emission quenching observed in devices utilizing luminescent materials such as solid thin films is a prevalent issue. Consequently, searching for new organic luminescent compounds exhibiting aggregation-induced emission (AIE) behavior and characterized by relatively simple and cost-effective synthesis is of crucial interest among applications from optoelectronics and organic lasing branches. Herein, we report the optical properties of three furan-based carbazole-substituted compounds, namely, tBuCBzSO 2 Ph, tBuCBzSPh, and tBuCbzTCF, exhibiting the aforementioned AIE phenomenon. The optical properties of dyes were determined in classical spectroscopic experiments supported by quantum-chemical calculations. The thermal investigations and electrochemical properties of dyes were performed to verify their usefulness in the construction of organic light-emitting diodes (OLEDs). In pursuit of this objective, OLEDs with a different design were fabricated, and their performance was subject to evaluation. In more detail, the different design strategies relying on the utilization of neat-dye films, as well as the preparation of dyedoped poly(9-vinylcarbazole):2-(4-tert-butylphenyl)-5-(4-biphenylyl)-1,3,4-oxadiazole (PVK:PBD) matrices were examined. The analysis that was conducted indicated the superior potential of tBuCBzSPh for optoelectronic applications. Notably, the positive impact of the AIE effect on the emission of the OLEDs and the ability to establish the lasing phenomenon in asymmetric, poly(methyl methacrylate) (PMMA)-doped polymeric slab waveguides were verified. The study showed that the combination of the strong intramolecular charge transfer (ICT) effect with dye aggregation enables the tuning of the emission of the OLED toward the first biological window, making examined dyes promising candidates for biomedical purposes. The same optical region can be attained for laser emission at relatively low pumping conditions, reaching as low as 7.3 kW of optical power for the tBuCBzSO 2 Ph compound.

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Electronic properties of carbazole/biphenylamino functionalized sulfone‐based host materials

Cited by 4 publications

References 51 publications

Design of N-heterocycle based-phthalonitrile/metal phthalocyanine–silver nanoconjugates for cancer therapies

Design of N-heterocycle based-phthalonitrile/metal phthalocyanine–silver nanoconjugates for cancer therapies

Exploring the Impact of Carbazole Position on Thermally Activated Delayed Fluorescence and Room-Temperature Phosphorescence Properties in Phthalimide–Carbazole Conjugates: A Density-Functional Theory Study

Emission in the Biological Window from AIE-Based Carbazole-Substituted Furan-Based Compounds for Organic Light-Emitting Diodes and Random Lasers

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