Heating and mechanical force-induced “turn on” fluorescence of cyanostilbene derivative with H-type stacking

Zhang, Yujian; Sun, Jingwei; Lv, Xiaojing; Ouyang, Mi; Cao, Feng; Pan, Guoxiang; Pan, Lina; Fan, Guangbo; Yu, Weiwei; He, Chao; Zheng, Sishi; Zhang, Feng; Wang, Wei; Zhang, Cheng

doi:10.1039/c3ce41221k

Cited by 49 publications

(27 citation statements)

References 31 publications

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“…As depicted in Figure S8, with the increase in pressure, the lifetime of the crystals clearly increased, similar to that observed under mechanical grinding. The molecular structure of pCN‐TPA was rather similar to that of ( Z )‐2‐(4′‐(diphenyl amino)‐[1,1′‐biphenyl]‐4‐yl)‐3‐(4‐methoxy‐phenyl)acrylonitrile ( α ‐CN‐TPA, Chart S1),13 which had a terminal cyano group in place of the methoxyl group. In the crystalline state, the α ‐CN‐TPA molecules with H‐aggregation adopted good coplanarity along the cyanostilbene moieties, which revealed a long lifetime (20.8 ns) due to the formation of the excimer.…”

Section: Resultsmentioning

confidence: 94%

“…The desired luminophore pCN-TPA was prepared by Suzuki coupling and Knoevenagel reaction according to the routes given in Scheme S1. Details of the synthetic procedures, 1 H NMR, 13 C NMR, and mass spectra are described in the experiment section. The UV/Vis and the PL spectra of pCN-TPA in various polar solvents are provided in the Supporting Information ( Figure S1 and S2).…”

Section: Resultsmentioning

confidence: 99%

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Multicolored‐Fluorescence Switching of ICT‐Type Organic Solids with Clear Color Difference: Mechanically Controlled Excited State

Zhang

Wang

Zhuang

et al. 2014

Chemistry A European J

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197

106

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A donor-acceptor-type fluorophore containing a twisted diphenylacrylonitrile and triphenylamine has been developed by using the Suzuki reaction. The system indicates typical intramolecular charge-transfer properties. Upon mechanical grinding or hydrostatic pressure, the fluorophore reveals a multicolored fluorescence switching. Interestingly, a fluorescence color transition from green to red was clearly observed, and the change of photoluminescent (PL) wavelength gets close to 111 nm. The mechanisms of high-contrast mechanochromic behavior are fully investigated by techniques including powder XRD, PL lifetime, high-pressure PL lifetime, and Raman spectra analysis. The tremendous PL wavelength shift is attributed to gradual transition of excited states from the local excited state to the charge-transfer state.

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Multicolored‐Fluorescence Switching of ICT‐Type Organic Solids with Clear Color Difference: Mechanically Controlled Excited State

Zhang

Wang

Zhuang

et al. 2014

Chemistry A European J

Self Cite

197

106

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“…Several other MRL materials showing on–off switching of photoluminescence have been reported. Zhang et al investigated arylamine derivatives showing the turn‐on behavior in response to mechanical stimuli . These compounds show little luminescence in the initial crystalline powder.…”

Section: Mechanically Induced On–off Switchingmentioning

confidence: 99%

Mechanoresponsive Luminescent Molecular Assemblies: An Emerging Class of Materials

et al. 2015

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Abstract:The possibility to change the morphology of organic and organometallic materials through mechanical stimulation is emerging as a general and powerful concept for the design of functional materials. In particular the photophysical properties, such as photoluminescence color, quantum yield and emission lifetime of organic and organometallic fluorophores can significantly depend on the molecular packing, enabling the development of molecular materials with mechanoresponsive luminescence characteristics. Indeed, an increasing number of studies have shown in recent years that mechanical force can be utilized to change the molecular arrangement, and thereby the optical response, of luminescent molecular assemblies of π-conjugated organic or organometallic molecules. This report reviews the development of such mechanoresponsive luminescent (MRL) molecular assemblies consisting of organic or organometallic molecules and summarizes emerging trends in this research field.After a brief introduction of mechanoresponsive luminescence observed in molecular assemblies, the concept of "luminescent molecular domino" is introduced, before molecular materials that show turn-on/off of photoluminescence in response to mechanical stimulation are reviewed. Mechanically stimulated multi-color changes and water-soluble MRL materials are also highlighted and approaches that combine the concept of MRL molecular assemblies with other materials types are presented in the last part of this progress report.

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“…Most TPA-dye-based donor-acceptor (D-A) structures show intramolecular CT and are sensitive to conformation (Zhang et al, 2015(Zhang et al, , 2013. However, the photophysical properties of form A and form B have no big difference even with distinct molecular conformations (Á = 3 nm).…”

Section: Figurementioning

confidence: 99%

Solvatochromism and mechanochromism observed in a triphenylamine derivative

Guo

Zhang

Zhu

et al. 2019

Acta Crystallogr Sect B

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A donor–π–acceptor fluorescent dye, 4‐[N,N‐di(4‐phenyl)amino]benzaldehyde 4‐chlorobenzoyl hydrazone (TPA‐CBH), based on a triphenylamine derivative (TPA) and 4‐chlorobenzoyl hydrazine (CBH) was designed and synthesized. The optical properties of this luminogen were investigated in solutions as well as in the solid states. In the intramolecular charge‐transfer (CT) mechanism, TPA‐CBH exhibits solvatochromism when dissolved in various polar solvents. Aggregation‐induced emission was observed with the changes of tetrahydrofuran/water ratios. In the solid state, mechanochromic fluorescence is observed when the samples are stressed under different conditions. Based on structural analyses and theoretical calculations, it is found that intra‐ and intermolecular CT processes play a key role in the diversity of fluorescent properties.

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Heating and mechanical force-induced “turn on” fluorescence of cyanostilbene derivative with H-type stacking

Cited by 49 publications

References 31 publications

Multicolored‐Fluorescence Switching of ICT‐Type Organic Solids with Clear Color Difference: Mechanically Controlled Excited State

Multicolored‐Fluorescence Switching of ICT‐Type Organic Solids with Clear Color Difference: Mechanically Controlled Excited State

Mechanoresponsive Luminescent Molecular Assemblies: An Emerging Class of Materials

Solvatochromism and mechanochromism observed in a triphenylamine derivative

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