Achieving very bright mechanoluminescence from purely organic luminophores with aggregation-induced emission by crystal design

Xu, Bingjia; Li, Wenlang; He, Jiajun; Wu, Shudong; Zhu, Qiangzhong; Yang, Zhiyong; Wu, Yuan‐Chun; Zhang, Yi; Jin, Can; Lu, Po‐Yen; Chi, Zhenguo; Liu, Siwei; Xu, Jiarui; Bryce, Martin R.

doi:10.1039/c6sc01325b

Cited by 132 publications

(70 citation statements)

References 38 publications

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“…However, the weak ML‐active TPA‐ph, TPA‐ p F, and ML‐inactive TPA‐ o F also have high lattice stabilities and still kept sharp diffraction peaks even after grinding heavily according to their PXRD spectra. In previous literatures, in some sense the higher the crystal lattice stability, the better the ML property . Higher crystal rigidity but worse ML property, the unusual phenomenon in this TPA‐based system has not been reported yet, and intrigued us to explore the deep relationship between crystal rigidity and ML performance.…”

Section: Resultsmentioning

confidence: 84%

Halogen‐Containing TPA‐Based Luminogens: Different Molecular Packing and Different Mechanoluminescence

Wang

Yao

et al. 2019

Advanced Optical Materials

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Organic mechanoluminescence (ML) materials have attracted much attention for their various application prospects in luminescent devices. However, the pace of their development has been greatly limited by the unclear inherent mechanism. Herein, halogen atoms are systematically introduced into ML for the first time to deeply explore the light‐emitting process and internal mechanism. Thus, a series of triphenylamine (TPA) derivatives is obtained with diverse ML properties, including TPA‐oF, TPA‐mF, TPA‐pF, TPA‐oCl, TPA‐mCl, TPA‐pCl, TPA‐oBr, TPA‐mBr, TPA‐pBr, and TPA‐ph. Among them, with the introduced chlorine and bromine atoms in the para‐position of the phenyl ring in TPA‐ph, the resultant TPA‐pCl and TPA‐pBr demonstrate bright ML; whereas the introduced fluorine atom in TPA‐pF drastically reduces the ML performance. Careful analysis of their optical properties and crystal structures coupled with theoretical calculations confirms that different halogen atoms in the TPA derivatives can really lead to diverse intermolecular interactions, and the strong intermolecular interactions are actually beneficial for the ML effect by reducing energy loss through nonradiative relaxation channels under a stimulus of mechanical force; however, unsatisfying ML performance is observed in the crystal with an overtight molecular packing, on account of the unbreakable crystals with high rigidity.

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Section: Resultsmentioning

confidence: 84%

Halogen‐Containing TPA‐Based Luminogens: Different Molecular Packing and Different Mechanoluminescence

Wang

Yao

et al. 2019

Advanced Optical Materials

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“…In 2016, Chi and team designed and synthesized very bright mechanoluminescent materials ( 6 a – e ) from purely organic luminophores with AIE features by taking the example of the above‐mentioned ML‐AIE materials 3 , 4 , and 5 . To use the new insights to ensure the ML emission mechanism utilizing AIE characteristics, the authors combined the concepts of prominent piezoelectric properties for molecular excitation with AIE phenomena for strong emission.…”

Section: Ml‐aie Materialsmentioning

confidence: 99%

Organic Mechanoluminescence with Aggregation‐Induced Emission

Ubba

Yang

et al. 2018

Chemistry An Asian Journal

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Mechanoluminescence (ML) involves the emission of light from various organic and inorganic materials upon mechanical stimulus. In this review, we contemplate the advances of metal-free, purely organic ML compounds with aggregation-induced emission (AIE), which give strong emission upon mechanical force. We show the new ML-AIE based materials can be used explore the basic of ML properties with structure-property relationships and molecular interactions. The flourishing idea of ML-AIE may help to find the characteristic and elusive component of ML as it partners with AIE, which upgrades the emission property in solids or aggregates. Recent advances in ML-AIE information could increase the wide scope of research in this expanding area, as these materials have promising applications in different optoelectronic areas.

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“…The synthesis of 35TPEBODP is shown in Scheme . It was prepared using microwave heating via the Knövenagel condensation of PhBODP and 4‐(1,2,2‐triphenylvinyl)benzaldehyde, which was facilely synthesized following modified procedures described in the literature, and its structural characterization was consistent with that given in the literature …”

Section: Resultsmentioning

confidence: 99%

Synthesis, photoluminescence, and electroluminescence characterization of double tetraphenylethene‐tethered BODIPY luminogens

Yang

Lee

Chen

2019

J Chinese Chemical Soc

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Three double tetraphenylethene (TPE)‐tethered 4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indance (BODIPY) fluorophores, 35TPEBODP, 88TPEBODP, and 26TPEBODP, have been synthesized and characterized. The green 35TPEBODP with deep red fluorescence shows serious thermal decomposition in the purification process of sublimation, which prohibits its test for an organic light‐emitting diode (OLED) fabricated by the vacuum–thermal evaporation process. The tethered TPE is attached to BODIPY at three different positions, resulting in different photoluminescence (emission wavelength and quantum yield) and electroluminescence (EL). Different from TPE‐tethered BODIPY fluorophores reported in literature, none of the BODIPY fluorophores studied here exhibits aggregation‐induced emission (AIE), aggregation‐induced enhanced emission (AIEE), or twisted intramolecular charge transfer (TICT) characteristics. Although solution (10−5 M THF) photoluminescence quantum yields (ϕs) are relatively high at 78%, 68%, and 86% for 35TPEBODP, 88TPEBODP, and 26TPEBODP, respectively, which are all higher than 41% of PhBODP (a non‐TPE‐tethered BODIPY), the ϕ is significantly decreased to 1–6% in 5 wt% dopant polystyrene thin film or as a solid powder, except for 13% of 26TPEBODP. Therefore, due to the low ϕ of dopant thin film or solid powder, either dopant or nondopant OLEDs exhibit inferior external quantum efficiency (EQE) and intensity of EL. The best OLED in this study is the 26TPEBODP device, and its EQE reaches 1.3%, and the highest EL intensity is approximately 1,600 cd/m2.

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Achieving very bright mechanoluminescence from purely organic luminophores with aggregation-induced emission by crystal design

Abstract: An effective strategy for the molecular design of AIE-ML materials is demonstrated based on tetraphenylethene with formyl substituents.

Cited by 132 publications

References 38 publications

Halogen‐Containing TPA‐Based Luminogens: Different Molecular Packing and Different Mechanoluminescence

Halogen‐Containing TPA‐Based Luminogens: Different Molecular Packing and Different Mechanoluminescence

Organic Mechanoluminescence with Aggregation‐Induced Emission

Synthesis, photoluminescence, and electroluminescence characterization of double tetraphenylethene‐tethered BODIPY luminogens

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