Luminogenic materials constructed from tetraphenylethene building blocks: Synthesis, aggregation-induced emission, two-photon absorption, light refraction, and explosive detection

Hu, Rongrong; Maldonado, José‐Luis; Rodríguez, Mario; Deng, Chunmei; Jim, Cathy Ka Wai; Lam, Jacky W. Y.; Yuen, Matthew Ming Fai; Ramos‐Ortíz, Gabriel; Tang, Ben Zhong

doi:10.1039/c1jm13556b

Cited by 226 publications

(122 citation statements)

References 60 publications

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“…In our D-TPE-A compounds, the degree of aggregation enhancement in the TPA cross section of DPA-TPE-CHO (1.1 times) is slightly smaller than that of the TPE-TPE-TPE molecule (about 2.8 times). 16 It is observed in our series of compounds as well as in the precedent literature 16 that the aggregation enhancement in TPA will become larger with longer effective π-electron conjugation, either by conjugately introducing donor/acceptor groups into monomers or by polymerization. One possible explanation of this phenomenon is suggested by Drobizhev et al 19 that the labile π-electron system enables charge density to be easily redistributed upon application of an external electric field.…”

Section: Resultsmentioning

confidence: 80%

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Aggregation Enhancement on Two-Photon Optical Properties of AIE-Active D-TPE-A Molecules

Zhang

Tang

et al. 2014

J. Phys. Chem. C

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We present an aggregation enhancement in two-photon-excited fluorescence (TPEF) of about 2 orders of magnitude in a series of novel noncentrosymmetric D-π-A molecules. Detailed analysis shows that their TPEF is enhanced concomitantly with both fluorescence quantum efficiency and two-photon absorptivity. These D-π-A molecules use tetraphenylethylene (TPE) as the π-bridge, giving them aggregation-induced emission characteristics. These branched or butterfly-configured molecules demonstrate two-photon absorption (TPA) transition bands similar to those in their linear absorption. The molecular TPA cross sections in the aggregation environment reach around 50−130 GM, and peak within the available wavelength range of a Ti:Sapphire femtosecond oscillator, which makes the molecules quite favorable for bioimaging applications. We observe that two-photon absorptivity increases progressively with the addition of more donor and acceptor moieties on the TPE backbone, which is presumably attributed to the improved conjugation length and enhanced intramolecular charge transfer, and hence better delocalization of π-electrons.

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Section: Resultsmentioning

confidence: 80%

“…14,15 The fluorescence quantum efficiencies of our D-TPE-A compounds are slightly lower than those of the π-TPE-π monomers with the same TPE core. 16 This reduction in quantum efficiencies in our D-π-A structures is presumably caused by the ICT effect between donors and acceptors. 6,17 3.2.…”

Section: Resultsmentioning

confidence: 98%

Aggregation Enhancement on Two-Photon Optical Properties of AIE-Active D-TPE-A Molecules

Zhang

Tang

et al. 2014

J. Phys. Chem. C

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“…[21] Compounds 2 and 3 were synthesized according to the literature method. [22][23][24] 1,3,3-Trimethylindolino-7'-bromobenzopyrylospiran (1 a Synthesis of 1-(4-vinylphenyl)-l,2,2-triphenylethylene (4) 4-(1,2,2-Triphenylvinyl)benzaldehyde (3) (3.6 g, 10 mmol) and methyltriphenylphosphonium bromide (4.3 g, 12 mmol) were dissolved in THF (15 mL) and THF (25 mL) solution containing potassium tertbutoxide (1.68 g, 15 mmol) was slowly added dropwise at 0 8C under a N 2 atmosphere. The reaction went on for 10 h. Then the reaction mixture was quenched with the addition of a saturated aqueous solution of sodium chloride (10 mL).…”

Section: Synthesis and Characterizationsmentioning

confidence: 98%

Reversible Multistimuli‐Response Fluorescent Switch Based on Tetraphenylethene–Spiropyran Molecules

Qian

et al. 2014

Chemistry A European J

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Two tetraphenylethene (TPE)-functionalized spiropyran (SP) molecules with very similar structure were designed and synthesized. The two molecules exhibit aggregation-induced emission (AIE) properties, as well as multistimuli-responsive color-changing properties, such as photochromism and acidchromism. The investigation of their different photochromic and acidchromic characteristics and dual-response fluorescent switch during isomerization indicated that the different link position between TPE and SP will significantly affect the extended π-conjugated system, resulting in completely different photochromic and acidchromic properties.

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“…8 In performance contents were than the P1 in for explosiv respectively. 9 pathways in t the Stern-Vo ..-f.…”

Section: Explosivementioning

confidence: 94%

Luminescent AIE materials for high-performance sensing applications

Leung

Tang²

2014

SPIE Proceedings

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Luminescent materials have been widely applied in chemo-and bio-sensing applications because these luminescent materials offer high signal-to-background ratio, superior sensitivity and broad dynamic ranges in various detections. Conventional luminogens suffer from aggregation-caused quenching (ACQ) effect due to strong π-π stacking interaction upon aggregate formation of the luminogens with analytes. Such ACQ effect limits the scope of practical sensing applications.Luminogens with aggregation-induced emission (AIE) characteristics enjoy high emission efficiency in solid or aggregated state while they are non-emissive in solution. AIE luminogens (AIEgens) tackle the lethal problem of ACQ materials in the sensing applications. Siloles and tetraphenylethene (TPE) are archetypal AIE cores and possess advantages of facile synthesis and readily functionalization.AIEgens have been utilized to develop various fluorescent chemosensors. For example, hyperbranched AIE polymers with different topologies can be worked as turn-off explosive sensor with high sensitivity. The explosive detections can be done in solid film, which facilitates practical usage. The AIEgens can also be used as sensors for volatile organic compounds and metal ions through alternating fluorescence on/off mechanisms.Besides chemosensor, the AIEgens have been applied in the fields of biology. Water-soluble AIEgens have been developed for quantifying nucleic acids and proteins. They can serve as bioprobes for real-time monitoring and studying the kinetic of protein conformational changes, making them promising for diagnostic and therapeutic applications. These demonstrations significantly expand the scope of analysis applications of AIEgens and offer new strategies to the design of new fluorescent chemo-and bio-sensors.

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Luminogenic materials constructed from tetraphenylethene building blocks: Synthesis, aggregation-induced emission, two-photon absorption, light refraction, and explosive detection

Cited by 226 publications

References 60 publications

Aggregation Enhancement on Two-Photon Optical Properties of AIE-Active D-TPE-A Molecules

Aggregation Enhancement on Two-Photon Optical Properties of AIE-Active D-TPE-A Molecules

Reversible Multistimuli‐Response Fluorescent Switch Based on Tetraphenylethene–Spiropyran Molecules

Luminescent AIE materials for high-performance sensing applications

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