Efficient piezochromic luminescence from tetraphenylethene functionalized pyridine-azole derivatives exhibiting aggregation-induced emission

Cui, Yinan; Yin, Yong-Min; Cao, Hong‐Tao; Zhang, Min; Shan, Guo‐Gang; Sun, Haizhu; Wu, Yong; Su, Zhong‐Min

doi:10.1016/j.dyepig.2015.03.024

Cited by 27 publications

(12 citation statements)

References 55 publications

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“…The solid-state emission of crystals of 96 is reversibly tuned from yellow or orange to red by grinding and fuming or heating processes [97]. In the same conditions, molecule 100 reported by Cui et al exhibits a color change from deep blue to turquoise [100]. Molecule 99 reported by Ma et al exhibits remarkable four-colour switching, by combining grinding/solvent-fuming cycles with protonation/deprotonation cycles based on exposure to HCl and NH 3 vapor [99].…”

Section: Tetraphenylethene Derivativesmentioning

confidence: 88%

“…Molecule 95, a highly conjugated -system with four BI units, has a yellowish green Figure 21. Molecular structure of TPE derivatives 87−90 [92], 91−94 [93], 95 [96], 96 [97], 97 and 98 [98], 99 [99], 100 [100] and 101−103 [101] with solid-state PL maxima (λ em ) and photoluminescence quantum yields (Φ PL ). emission at 525 nm [96].…”

Section: Tetraphenylethene Derivativesmentioning

confidence: 99%

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Recent Trends in the Design, Synthesis, Spectroscopic Behavior, and Applications of Benzazole-Based Molecules with Solid-State Luminescence Enhancement Properties

Fery–Forgues

Vanucci-Bacqué

2021

Top Curr Chem (Z)

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Molecules that exhibit solid-state luminescence enhancement, i.e. the rare property to be more strongly emissive in the solid state than in solution, find an increasing number of applications in the fields of optoelectronic and nanophotonic devices, sensors, security papers, imaging and theranostics. Benzazole (BZ) heterocycles are of particular value in this context. The simple enlargement of their πelectron system using a -C=C-Ar, or -N=C-Ar moiety is enough for intrinsic SLE properties to appear. Their association with a variety of polyaromatic motifs leads to SLE-active molecules that frequently display attractive electroluminescent properties and are sensitive to mechanical stimuli. The excitedstate intramolecular proton transfer (ESIPT) process that takes place in some hydroxy derivatives reinforces the SLE effect and allows the development of new sensors based on a protection/deprotection strategy. BZ may also be incorporated into frameworks that are prototypical aggregation-induced enhancement (AIE) luminogens, such as the popular tetraphenylethene (TPE), leading to materials with excellent optical and electroluminescent performance. This review encompasses the various ways to use benzazole units in SLE systems. It underlines the significant progresses recently made in the understanding of the photophysical mechanisms involved. A brief overview of the synthesis shows that BZ units are robust building blocks, easily incorporated into a variety of structures. Generally speaking, we try to show how advantage may be taken from these small heterocycles for the design of increasingly efficient luminescent materials.

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Section: Tetraphenylethene Derivativesmentioning

confidence: 88%

Section: Tetraphenylethene Derivativesmentioning

confidence: 99%

Recent Trends in the Design, Synthesis, Spectroscopic Behavior, and Applications of Benzazole-Based Molecules with Solid-State Luminescence Enhancement Properties

Fery–Forgues

Vanucci-Bacqué

2021

Top Curr Chem (Z)

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“…They constructed the non-doped multilayer devices using these derivatives as emitting layers, which showed good performance. 21 Tang and his co-workers got a series of bifunctional materials with excellent blue light-emitting and holetransporting properties by combining TPE group and carbazole group in the same molecule. 22 Li and his co-workers designed and synthesized a novel series of TPE-based molecules by introducing the hole-dominated triphenylamine (TPA) or methyl-substituted TPA moieties, which exhibited excellent blue light-emitting and hole-transporting properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, aggregation-induced emission, and electroluminescence of a new compound based on tetraphenylethene, carbazole, and dimesitylboron moieties

Dong¹,

Li²,

Shi³

et al. 2016

Tetrahedron

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A novel molecule, 3,6-bis(dimesitylboryl)-9-(4-(1,2,2-triphenylvinyl)phenyl)-9H-carbazole (DTPC), was synthesized by introducing two dimesitylboron groups and one tetraphenylethene group to the 3position, 6-position, and 9-position of carbazole, respectively. The structure of DTPC was fully characterized by proton nuclear magnetic resonance spectroscopy, mass spectrometry, and elemental analysis. The thermal, electrochemical, and photophysical properties of DTPC were studied by thermogravimetry in conjunction with electrochemistry, UVevis absorption spectroscopy and fluorescence spectroscopy. The results reveal that DTPC has excellent aggregation-induced emission properties. The multilayer electroluminescent device fabricated by using DTPC as light-emitting layer emits the blue light (l max 489 nm) with CIE coordinates (0.17, 0.29) and shows good electroluminescent performances with the turn-on voltage of 5.7 V, maximum luminance of 5709 cd/m 2 (at 15 V) and maximum luminance efficiency of 4.31 cd/A

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“…9a, 2-F; 9b, 3-F; 9c, 4-F; 9d, 2,3-F 2 ; 9e, 2,4-F 2 ; 9f, 2,5-F 2 ; 9g, 2,6-F 2 ; 9h, 3,4-F 2 ; 9i, 3,5-F 2 ; 9j, 2,4,6-F 3 ; 9k, 3,4,5-F 3 9l, 2-F; 9m, 3-F 9p, 3-F; 9q, 4-F F F 9n, 3-F; 9o, 4 [11] ), 其固体显示 MCL 特性. 2015 年, 单国刚等 [37] 通过 Suzuki 偶联反应, 合成了 [33] Figure 1 Comparison of some photophysical properties of compounds TPE, 9c and 9q [33] O…”

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Advances in Organofluorine Compounds with Aggregation-Induced Emission

Qin¹,

Liu²,

Nie³

et al. 2020

Chin. J. Org. Chem.

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Aggregation-induced emission (AIE) compounds have attracted much attention due to their important potential applications in biological and chemical sensing, luminescent materials, display and other areas. As an important class of functional molecules, organofluorine compounds have been widely studied in areas such as organic chemitry and materials chemistry. The organofluorine compounds with AIE properties are summarized and classified. The currently reported AIE organofluorine compounds include the fluorinated tetraphenylethene (TPE) derivatives, 9,10-distyrylanthracene (DSA) derivatives, cyanostilbene derivatives, distyrylbenzene derivatives, fluorinated polymers, carborane clusters, room temperature phosphorescent molecules, and some other fluorinated structures. With fluorine atoms in the structures, the stability of the resulting AIE compounds is generally improved, and fluorine atoms often participate in the intermolecular interactions leading to significant changes in the structure of the aggregation state, and hence changes in luminescence properties, for example, emission enhancement, bathochromism or hypsochromism of the emissions, improvement of the emission quantum yield and lifetime. The prospects of the future study are also discussed.

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Efficient piezochromic luminescence from tetraphenylethene functionalized pyridine-azole derivatives exhibiting aggregation-induced emission

Cited by 27 publications

References 55 publications

Recent Trends in the Design, Synthesis, Spectroscopic Behavior, and Applications of Benzazole-Based Molecules with Solid-State Luminescence Enhancement Properties

Recent Trends in the Design, Synthesis, Spectroscopic Behavior, and Applications of Benzazole-Based Molecules with Solid-State Luminescence Enhancement Properties

Synthesis, aggregation-induced emission, and electroluminescence of a new compound based on tetraphenylethene, carbazole, and dimesitylboron moieties

Advances in Organofluorine Compounds with Aggregation-Induced Emission

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