Expression of anti-Kasha's emission from amino benzothiadiazole and its utilization for fluorescent chemosensors and organic light emitting materials

Peng, Zhixing; Wang, Zaibin; Huang, Ze-Ning; Liu, Shaojie; Lü, Ping; Wang, Yanguang

doi:10.1039/c8tc02416b

Cited by 32 publications

(22 citation statements)

References 46 publications

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“…Unfortunately, examples of anti‐Kasha transitions are still far less common than those obeying Kasha's rule due to the unclear molecular design . On the other hand, the reported systems with anti‐Kasha transitions such as azulenes, acenes, and polyenes are synthesized following traditional molecular design and display mainly planar conjugated structures . Consequently, although these compounds exhibit anti‐Kasha luminescence behavior in the solution state, what happens in aggregates and the solid state is still ambiguous because their emission is mostly quenched in aggregates.…”

Section: Aie and The Research Branchesmentioning

confidence: 99%

Aggregation‐Induced Emission: New Vistas at the Aggregate Level

et al. 2020

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Aggregation‐induced emission (AIE) describes a photophysical phenomenon in which molecular aggregates exhibit stronger emission than the single molecules. Over the course of the last 20 years, AIE research has made great strides in material development, mechanistic study and high‐tech applications. The achievements of AIE research demonstrate that molecular aggregates show many properties and functions that are absent in molecular species. In this review, we summarize the advances in the field of AIE and its related areas. We specifically focus on the new properties of materials attained by molecular aggregates beyond the microscopic molecular level. We hope this review will inspire more research into molecular ensembles at and beyond the meso level and lead to the significant progress in material and biological science.

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Section: Aie and The Research Branchesmentioning

confidence: 99%

Aggregation‐Induced Emission: New Vistas at the Aggregate Level

et al. 2020

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“…Then we tried various functionals including M06, M062X, MPW1B95, PBE33, PBE38, and PBE0 that have different Hartree–Fock hybrid proportions to optimize the structure, and the f values are still nearly equal to zero for the electronic transition from S 1 to S 0 (Table S2, Supporting Information), disclosing that S 1 is indeed a dark state. Instead, the efficient emission of DMF‐BP‐PXZ actually should originate from the radiative relaxation of the higher energy electronic excited state, which doesn't obey Kasha's rule . Next, the second excited state (S 2 ) geometry was further optimized using the MPW1B95 and PBE0 functional.…”

Section: Resultsmentioning

confidence: 99%

Mechanical Insights into Aggregation‐Induced Delayed Fluorescence Materials with Anti‐Kasha Behavior

et al. 2018

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Organic materials with aggregation‐induced delayed fluorescence (AIDF) have exhibited impressive merits for improving electroluminescence efficiency and decreasing efficiency roll‐off of nondoped organic light‐emitting diodes (OLEDs). However, the lack of comprehensive insights into the underlying mechanism may impede further development and application of AIDF materials. Herein, AIDF materials consisting of benzoyl serving as an electron acceptor, and phenoxazine and fluorene derivatives as electron donors are reported. They display greatly enhanced fluorescence with increased delayed component upon aggregate formation. Experimental and theoretical investigations reveal that this AIDF phenomenon can be rationally ascribed to the suppression of internal conversion and the promotion of intersystem crossing in solid. Moreover, the theoretical calculations disclose that the efficient solid‐state delayed fluorescence originates from the higher energy electronic excited state (e.g., S2) rather than the lowest energy‐excited state (S1), demonstrating an anti‐Kasha behavior. The excellent AIDF property allows high exciton utilization and thus superb performance of OLEDs using these new materials as light‐emitting layers.

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“…[4] In the screening of the various donors by surfing the literature, azepane, [5] was selected in this study for its easier structural modification by installing phenyl groups, [6] the magnified absorptivity in comparison with other nitrogen-containing rings, such as aziridine, azetidine, pyrrolidine and piperidine [7] and so far their multiple achievements in thermally activated delayed fluorescence emitter, [8] dye-sensitized solar cell, [9] polymer LEDs [10] and the ultrasensitive fluorescence sensor. [11] Combining with our previous works on benzothiadiazole (BTD) on the development of new fluorescent compounds for optoelectronic materials and fluorescent probes, [12] azepane (AP), iminodubenzyl (IDB) and iminostilbene (ISB) were respectively installed on 5-position of BTD, affording compounds 1, 2 and 3 for the systematical investigation of the fluorescent structure-property relationship (FSPR).…”

Section: Introductionmentioning

confidence: 89%

Preparation and Photoluminescent Properties of Three 5‐Amino Benzothiadiazoles (5‐amBTDs)

Wang

Lü

et al. 2020

Chemistry An Asian Journal

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Three DÀ A compounds were designed and synthesized based on a benzothiadiazole acceptor. Azepane (AP), iminodubenzyl (IDB) and iminostilbene (ISB) were used, respectively, as donors and installed on the 5-position of BTD to afford 1, 2 and 3, respectively. Their photophysical properties in different states (solution, film, crystal, and powder) are systematically investigated. Among them, AIEactive compounds 2 and 3 were found to have good sensitivity toward viscosity and display quite good linear relationship with an increase in viscosity. Compound 2 displayed dual emission in solutions which largely depended on the polarity of the solvent. Meanwhile, compound 2 exhibits a mechanochromic character with disappearance and reappearance of a dual-emissive peak induced by mechanical grinding and solvent fuming. Furthermore, these three compounds can be used in the fabrication of blue OLED devices.

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Expression of anti-Kasha's emission from amino benzothiadiazole and its utilization for fluorescent chemosensors and organic light emitting materials

Abstract: Emission of amino benzothiadiazoles is controllable and might be used for white solution emission, fluorescent chemosensors, and emitting materials in OLEDs.

Cited by 32 publications

References 46 publications

Aggregation‐Induced Emission: New Vistas at the Aggregate Level

Aggregation‐Induced Emission: New Vistas at the Aggregate Level

Mechanical Insights into Aggregation‐Induced Delayed Fluorescence Materials with Anti‐Kasha Behavior

Preparation and Photoluminescent Properties of Three 5‐Amino Benzothiadiazoles (5‐amBTDs)

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