The solvatochromism and aggregation-induced enhanced emission based on triphenylamine-propenone

Liang, Zuoqin; Wang, Xiaomei; Dai, Guoliang; Ye, Changqing; Zhou, Yuyang; Tao, Xutang

doi:10.1039/c5nj01072a

Cited by 41 publications

(27 citation statements)

References 36 publications

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“…The significant ICT in the excited state could be the probable factor for moderate Stokes shift for the compounds in solutions and ESIPT process for compound II in solid state. High fluorescence quantum efficiency in solution is a common characteristic of the donor–acceptor type of chromophores . Red shifts of emission spectra with fluorescence quenching in the solid state are the most common limitations of the reported donor–acceptor system, these were overcome by present compounds I and III .…”

Section: Resultsmentioning

confidence: 98%

π–π Interactions: Influence on Molecular Packing and Solid‐State Emission of ESIPT and non‐ESIPT Motifs

et al. 2016

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Novel, triphenylamino benzothiazole-based excited-state intramolecular protont ransfer (ESIPT) and non-ESIPT fluorophores were prepared by Suzuki coupling reactions. Their photophysical properties in solution,a queous suspension,a nd in the solids tate were systematically investigated. High fluorescenceq uantum efficiencies (F sol % 95 %; F solid % 88 %), moderate Stokes shifts ( % 8000 cm À1 ), microenvironment-sensitive and molecular-framework-dependent emission are the striking features of the protocol described here. Solid-state emission was modulated and interpreteda s ac rossover effect of p-p interactions using single-crystal Xray analyses. The nonplanar/twisted framework of the system helps to avoid noncovalenti nteractions, facilitating the suppression of fluorescenceq uenching in the solid state with high quantum efficiency over 88 %.[a] Dr.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.

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Section: Resultsmentioning

confidence: 98%

π–π Interactions: Influence on Molecular Packing and Solid‐State Emission of ESIPT and non‐ESIPT Motifs

et al. 2016

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“…TPA-CBH, which consists of electron-donating TPA, electron-accepting chlorobenzene and a conjugated chain, is a typical D--A molecule with clear intramolecular CT properties . Photophysics of the D--A conjugation in solutions are dramatically dependent on the solvent polarity (Liang et al, 2015;Yang et al, 2013;Zhang et al, 2015), so the absorption and emission properties of TPA-CBH were investigated in various solvents. There are no significant changes in the absorption spectra ( Fig.…”

Section: Resultsmentioning

confidence: 99%

“…In contrast with conventional fluorescent molecules which suffer from aggregation caused quenching (ACQ), the AIE-active molecules are highly fluorescent in the aggregation process. MCF materials are a class of 'smart' materials with variable fluorescent properties that change in response to external force stimuli (Chi et al, 2012), such as organic solvent vapour, pressure and heat, etc Zhang et al, 2015Zhang et al, , 2017Liang et al, 2015;Li et al, 2017;. The MCF property in AIE active materials was first reported by Yoon et al (2010).…”

Section: Introductionmentioning

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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“…A decrease in solvent polarity resulting in a slight blue shift of the emission center ( Fig. S1 of the supporting information) is indicative of ICT contribution to emission (Liang et al, 2015). Ethanolic solutions of 1a, 1b and 1c have very low fluorescence [ Fig.…”

Section: Photophysical Properties Of Compounds 1a-1cmentioning

confidence: 99%

Stimuli-responsive aggregation-induced fluorescence in a series of biphenyl-based Knoevenagel products: effects of substituent active methylene groups on π–π interactions

Sarma

Patir

Sarmah

et al. 2019

Acta Crystallogr B Struct Sci Cryst Eng Mater

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A series of three biphenyl‐based Knoevenagel products (denoted 1a, 1b, 1c) with active methylene groups has been synthesized. Compounds 1a and 1b show strong solid‐state fluorescence, whereas 1c displays low emission. Effects of substituent groups in condensed phase packing of the molecules have been investigated and correlated with their photophysical properties. Interestingly, compound 1a exhibits mechanofluorochromism with emission color changes from yellow to green (wavelength shift of 40 nm) after mechanical grinding. Furthermore, fluorescence of 1a and 1b is turned off under alkaline conditions, making them potential candidates for aggregation‐enhanced emission‐based pH sensors.

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The solvatochromism and aggregation-induced enhanced emission based on triphenylamine-propenone

Abstract: The weak intermolecular interactions and the suppression of the intramolecular charge transfer result in the efficient aggregation-induced enhanced emission characteristic of PhO-TPA and PyO-TPA.

Cited by 41 publications

References 36 publications

π–π Interactions: Influence on Molecular Packing and Solid‐State Emission of ESIPT and non‐ESIPT Motifs

π–π Interactions: Influence on Molecular Packing and Solid‐State Emission of ESIPT and non‐ESIPT Motifs

Solvatochromism and mechanochromism observed in a triphenylamine derivative

Stimuli-responsive aggregation-induced fluorescence in a series of biphenyl-based Knoevenagel products: effects of substituent active methylene groups on π–π interactions

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