Aggregation-induced emission (AIE)-active phenanthrenequinone hydrazone-based dyes with reversible mechanofluochromism

Yan, Xufeng; Zhu, Pengcheng; Yang, Li; Yuan, Shuang; Lan, Haichuang; Xiao, Shuzhang

doi:10.1016/j.mtcomm.2019.100565

Cited by 6 publications

(3 citation statements)

References 49 publications

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“…Precursors in Scheme 1 were prepared according to literature procedure. 46 The precursors (6.7 mmol) and triethylamine (48.3 mmol, 6.7 mL) were dissolved in anhydrous dichloromethane (30.0 mL) and stirred at ice bath for 10 min under an atmosphere of argon. Then boron triuoride etherate (73.8 mmol, 9.1 mL) was added, and the resultant mixture was stirred at room temperature overnight.…”

Section: Synthesismentioning

confidence: 99%

Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence

et al. 2019

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Section: Synthesismentioning

confidence: 99%

Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence

et al. 2019

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“…24 A special type of AIE, crystallization-induced emission enhancement (CIEE), has been observed in a hydrazone-based emitter. 25 In such cases, the luminophore is weakly emissive in the amorphous state but becomes highly emissive in the crystalline state, which could be utilized as stimuli-responsive (e.g., piezo or temperature) fluorescent materials.…”

Section: Introductionmentioning

confidence: 99%

Microcrystal Electron Diffraction Elucidates Water-Specific Polymorphism-Induced Emission Enhancement of Bis-arylacylhydrazone

Cho

Kim

et al. 2021

ACS Appl. Mater. Interfaces

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Aggregation-induced emission (AIE) phenomena have gained intense interest over the last decades because of its importance in solid-state emission. However, the elucidation of a working mechanism is difficult owing to the limited characterization methods on solid-state molecules, further complicated if dynamic structural changes occur. Here, a series of bis-arylacylhydrazones (BAHs) were synthesized, for which their AIE properties are only turned on by the reversible adsorption of water molecules. We used microcrystal electron diffraction (MicroED) to determine the molecular structures of two BAHs directly from bulk powders (without attempting to grow crystals) prepared in the absence or presence of water adsorption. This study reveals the unambiguous characterization of the dependence of crystal packing on the specific cocrystallization with hydrates. The structural analysis demonstrates that water molecules form strong hydrogen bonds with three neighboring BAH-1, resulting in the almost complete planarization and restriction of the intramolecular rotation of the molecule. MicroED plays an important role in providing a decisive clue for the reversible polymorphism changes induced by the adsorption of water molecules, regulating emissive properties.

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“…In 2019, Yan and coworkers developed two novel solid‐emissive BODIHY systems, 57 and 58 (Figure 17A), which use phenanthrenequinone hydrazone derivatives as ligands. [ 72 ] The precursors were prepared according to modified literature procedures [ 73 ] followed by treatment with BF 3 ·Et 2 O to produce dyes 57 and 58 as red solids in yields of 95% and 90%, respectively.…”

Section: Phenanthrenequinone‐based Bodihy Systemsmentioning

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)-active phenanthrenequinone hydrazone-based dyes with reversible mechanofluochromism

Cited by 6 publications

References 49 publications

Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence

Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence

Microcrystal Electron Diffraction Elucidates Water-Specific Polymorphism-Induced Emission Enhancement of Bis-arylacylhydrazone

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

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