AIE-active boron complexes based on benzothiazole–hydrazone chelates

Duan, Wenzeng; Liu, Qingsong; Huo, Yanmin; Cui, Jichun; Gong, Shuwen; Liu, Zhipeng

doi:10.1039/c8ob00755a

Cited by 25 publications

(9 citation statements)

References 37 publications

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“…Inspired by the AIE-active BOIDPY analogs based on pyridine-hydrazone ligands, a group of new AIE-active monoboron ( 28 ) and bisboron ( 29 ) difluoride complexes was developed by adopting benzo[ d ]thiazole-hydrozone as the chelates (Duan et al, 2018). Similar to compound 27a , these complexes showed weak emission ( Φ f < 1%) and large Stokes shifts (up to 7,400 cm −1 ) in a diluted solution and AIEE in the aggregation state.…”

Section: Bodipy Analogs With Aiementioning

confidence: 99%

Recent Progress of BODIPY Dyes With Aggregation-Induced Emission

et al. 2019

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With the development of organic optoelectronic materials and bioimaging technology, to exploit organic luminescent materials with high luminescent efficiency in aggregation-state has become a research hotspot. BODIPYs have become one of the research objects of this kind of material because of their obvious advantages. This review focuses on the design and synthesis of AIE-type BODIPYs, the mechanism of AIE properties and their applications in recent years. Through classification, analysis, and summary, this review aims to explore the structure-activity relationship of AIE-type BODIPYs and to provide ideas for the further design and potential applications of AIE-active fluorescent materials.

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Section: Bodipy Analogs With Aiementioning

confidence: 99%

Recent Progress of BODIPY Dyes With Aggregation-Induced Emission

et al. 2019

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“…Inspired by the use of heterocyclic-based hydrazones, which are known to be useful building blocks for the generation of new luminescent complexes, [63] Duan et al synthesized mono-and binuclear boron complexes based on benzothiazole-hydrazone chelates (Figure 12A). [64] Compounds 37-40 were synthesized via a three-step procedure starting from 2-benzothiazoleacetonitrile and the corresponding diazonium salt to form the appropriate benzothiazole-hydrazone ligand. Next, the ligands were subjected to adapted literature procedures [32,37] to form BODIHYs 37 and 38 in yields of 65% and 22%, respectively.…”

Section: Benzothiazole-based Bodihy Derivativesmentioning

confidence: 99%

Boron difluoride hydrazone (BODIHY) complexes: A new class of fluorescent molecular rotors

Bismillah

Aprahamian

2023

J of Physical Organic Chem

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Fluorescent dyes exhibiting luminescence in the solid state are crucial for the development of efficient solid-state lighting devices. Most fluorophores though do not emit in the solid state, mainly as a result of intermolecular interactions that cause emission quenching. Boron difluoride hydrazone (BODIHY) dyes are peculiar in this sense as their emission is drastically enhanced when transferred from solution to the solid state. The BODIHY dyes are easy to synthesize and derivatize, have tunable absorption and emission profiles and large Stokes shifts, which are all desirable characteristics from solid-state emitters. Here, we summarize the discovery and development of BODIHY dyes including the tuning of their photophysical properties through structure-property analyses.

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“…Aggregation‐induced emission (AIE) describes the behavior of organic molecules that exhibit dim or no emission in dilute solutions but significantly enhanced luminescence in aggregates or in the solid state, which has been widely accepted to be an efficient strategy exploiting the reduction of rotovibrational relaxation pathways. [ 6 ] In recent years, a number of AIE‐active organic BF 2 complexes have been achieved, [ 7 , 8 , 9 , 10 , 11 ] and their applications as aggregate‐state emitters for OLEDs, stimuli‐response switches, and in other fields have also been demonstrated. [ 12 ] Despite tremendous efforts over the last decade, the design and application of the AIE‐active BF 2 complexes is still facing significant challenges.…”

Section: Introductionmentioning

confidence: 99%

AIE‐Active Difluoroboron Complexes with N,O‐Bidentate Ligands: Rapid Construction by Copper‐Catalyzed C−H Activation

et al. 2021

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The development of organic materials with high solid-state luminescence efficiency is highly desirable because of their fundamental importance and applicability in optoelectronics. Herein, a rapid construction of novel BF 2 complexes with N,O-bidentate ligands by using Cu(BF 4 ) 2 •6H 2 O as a catalyst and BF 2 source is disclosed, which avoids the need for pre-composing the N,O-bidentate ligands and features a broad substrate scope and a high tolerance level for sensitive functional groups. Moreover, molecular oxygen is employed as the terminal oxidant in this transformation. A library of 36 compounds as a new class of BF 2 complexes with remarkable photophysical properties is delivered in good to excellent yields, showing a substituent-dependency on the photophysical properties, derived from the -* character of the photoexcited state. In addition, aggregation-induced emission (AIE) is observed and quantified for the brightest exemplars. The excited state properties are fully investigated in solids and in THF/H 2 O mixtures. Hence, a new series of photofunctional materials with variable photophysical properties is reported, with potential applications for sensing, bioimaging, and optoelectronics.

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AIE-active boron complexes based on benzothiazole–hydrazone chelates

Cited by 25 publications

References 37 publications

Recent Progress of BODIPY Dyes With Aggregation-Induced Emission

Recent Progress of BODIPY Dyes With Aggregation-Induced Emission

Boron difluoride hydrazone (BODIHY) complexes: A new class of fluorescent molecular rotors

AIE‐Active Difluoroboron Complexes with N,O‐Bidentate Ligands: Rapid Construction by Copper‐Catalyzed C−H Activation

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