Evidence for Aggregation-Induced Emission from Free Rotation Restriction of Double Bond at Excited State

Xiong, Jia-Bin; Yuan, Ying-Xue; Wang, Lian; Sun, Jianhua; Qiao, Weiguo; Zhang, Hongchao; Duan, Miao; Han, Hongwei; Zhang, Song; Zheng, Yan‐Song

doi:10.1021/acs.orglett.7b03662

Cited by 111 publications

(65 citation statements)

References 32 publications

(38 reference statements)

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“…[1][2][3][4][5][6][7][8] The recently discovered aggregation-inducede mission (AIE) has become one of top research frontiers in chemistry and materials due to great potential in solid emitter andc hemo/biological sensors. [9][10][11][12][13] Up to now,al arge number of sensors based on AIEgens have been developed. [14][15][16][17][18][19][20] Some of them show valuablea pplication prospecti nm onitoring,a nalysis, imaging of ions.…”

mentioning

confidence: 99%

Selective Fluorescence Turn‐On Sensing of Phosphate Anion in Water by Tetraphenylethylene Dimethylformamidine

Yuan

Wang

Zheng

2019

Chemistry An Asian Journal

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A tetraphenylethylene (TPE) derivative bearing two dimethylformamidine units was synthesized. The dihydrogen chloride salt of this TPE derivative was soluble in water and showed almost no emission. By addition of phosphate anions, the dihydrogen chloride salt could be transformed into the monohydrogen chloride salt, which was barely soluble and emitted strong fluorescence through aggregation‐induced emission (AIE), while many other anions could not bring about a fluorescence enhancement. Meanwhile, the dihydrogen chloride salt and monohydrogen chloride salt could be reversible transformed by addition of acid and base alternately in the presence of phosphate anion, which led to fluorescence turn‐on and turn‐off. Therefore, the TPE dimethylformamidine holds potential for selectively sensing phosphate anions in water and use as fluorescence pH switch. This study provided a new approach to AIEgen sensors by using formamidine groups.

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confidence: 99%

Selective Fluorescence Turn‐On Sensing of Phosphate Anion in Water by Tetraphenylethylene Dimethylformamidine

Yuan

Wang

Zheng

2019

Chemistry An Asian Journal

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“…Xiong et al observed an interesting phenomenon of TPE derivatives, as shown in Figure 4a. [44] When the phenyl groups of TPE were connected by short rigid tethers, the resultant TPE tetracycle emitted strong fluorescencei ns olution. Through an elaborate chemical design, they found that cis-TPE bicycles (1, 2, and 5) emitted strong green, yellow,a nd green emissions, respectively,w hereas gem-TPE bicycle( 3, 4, and 6) did not ex-hibit fluorescencei nT HF solution under the irradiation of aU V lamp (l = 365 nm;F igure 4b).…”

Section: Rir Versus Z/e Isomerizationmechanism For Tpe Derivativesmentioning

confidence: 99%

“…C) Representation of double-bond rotationint he excitedstate. Reproduced with permission from Ref [44]…”

mentioning

confidence: 99%

Recent Advances in the Z/E Isomers of Tetraphenylethene Derivatives: Stereoselective Synthesis, AIE Mechanism, Photophysical Properties, and Application as Chemical Probes

Xie

2019

Chemistry An Asian Journal

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Focused research on the Z/E isomerso ft etraphenylethene (TPE) derivatives is scarce in comparison with the thousands of luminogens with AIE properties (AIEgens) that have been synthesized based on the TPE moiety.T he similar chemical and physical properties of the Z/E isomersm ake them difficult to separate by using conventional chromatographic techniques.H owever,t hey can be isolated by introducing polar groupsa nd the pure isomers exhibit very different photophysical properties, mechanochromism, and host-guestc oordination,a sw ell as assisting in deciphering the AIE mechanism. In this Minireview, we present an overview of the disagreement regarding the AIE mechanism between the restriction of intramolecular vibration and photoinduced Z/E isomerization. Then, we discuss the development of (Z)-/(E)-TPE derivatives, their use in host-guest detection, and their mechanoluminescence properties, with a focus on their photophysical characteristics. Finally,w ee xplore the stereoselective synthesis of pure (Z)-/(E)-TPE derivatives.

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“…Although the intramolecular rotation is generally related to the rotation of a single bond, Xiong et al 41 proved the rotation of a double bond at the excited state will result in the fluorescence quenching of AIEgens in solution. They synthesized a series of TPE macrocycles to observe their fluorescence in tetrahydrofuran solution, because the TPE has simple molecular structure but splendid AIE characteristics.…”

Section: Restriction Of Intramolecular Motionmentioning

confidence: 99%

A new approach to developing diagnostics and therapeutics: Aggregation‐induced emission‐based fluorescence turn‐on

Guo

Song

et al. 2019

Medicinal Research Reviews

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Fluorescence imaging is a promising visualization tool and possesses the advantages of in situ response and facile operation; thus, it is widely exploited for bioassays. However, traditional fluorophores suffer from concentration limits because they are always quenched when they aggregate, which impedes applications, especially for trace analysis and real‐time monitoring. Recently, novel molecules with aggregation‐induced emission (AIE) characteristics were developed to solve the problems encountered when using traditional organic dyes, because these new molecules exhibit weak or even no fluorescence when they are in free movement states but emit intensely upon the restriction of intramolecular motions. Inspired by the excellent performances of AIE molecules, a substantial number of AIE‐based probes have been designed, synthesized, and applied to various fields to fulfill diverse detection tasks. According to numerous experiments, AIE probes are more practical than traditional fluorescent probes, especially when used in bioassays. To bridge bioimaging and materials engineering, this review provides a comprehensive understanding of the development of AIE bioprobes. It begins with a summary of mechanisms of the AIE phenomenon. Then, the strategies to realize accurate detection using AIE probes are discussed. In addition, typical examples of AIE‐active materials applied in diagnosis, treatment, and nanocarrier tracking are presented. In addition, some challenges are put forward to inspire more ideas in the promising field of AIE‐active materials.

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Evidence for Aggregation-Induced Emission from Free Rotation Restriction of Double Bond at Excited State

Abstract: This paper reports that cis-TPE dicycles emit strong fluorescence, while the gem dicycles show almost no emission in solution, demonstrating that the free rotation restriction of the double bond at the excited state is the key factor for AIE effects.

Cited by 111 publications

References 32 publications

Selective Fluorescence Turn‐On Sensing of Phosphate Anion in Water by Tetraphenylethylene Dimethylformamidine

Selective Fluorescence Turn‐On Sensing of Phosphate Anion in Water by Tetraphenylethylene Dimethylformamidine

Recent Advances in the Z/E Isomers of Tetraphenylethene Derivatives: Stereoselective Synthesis, AIE Mechanism, Photophysical Properties, and Application as Chemical Probes

A new approach to developing diagnostics and therapeutics: Aggregation‐induced emission‐based fluorescence turn‐on

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