Mechanochromic and thermochromic fluorescent properties of cyanostilbene derivatives

Zhang, Yujian; Zhuang, Guilin; Ouyang, Mi; Hu, Bin; Song, Qingbao; Sun, Jingwei; Zhang, Cheng; Gu, Cheng; Xu, Yixin; Ma, Yan

doi:10.1016/j.dyepig.2013.03.017

Cited by 77 publications

(31 citation statements)

References 32 publications

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“…In contrast, the PXRD of the ground solid exhibits weak and board signals. The reduction in the diffraction peaks intensity and/or number demonstrates a morphological transition from the crystalline to amorphous [54,55]. Similar observations are also found in C1 and C2 (Fig.…”

Section: Piezochromic Behaviorsupporting

confidence: 82%

Efficient piezochromic luminescence from tetraphenylethene functionalized pyridine-azole derivatives exhibiting aggregation-induced emission

et al. 2015

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Section: Piezochromic Behaviorsupporting

confidence: 82%

Efficient piezochromic luminescence from tetraphenylethene functionalized pyridine-azole derivatives exhibiting aggregation-induced emission

et al. 2015

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“…Not only the cyano-functionalized probes, but other functional groups containing probes have also been reported to have good AIEE active properties in different solvent mixtures, such as carbazole [42], diphenylamine [43], tetraphenylethene [44], hexaphenylsilole [45], and naphthalimide [46]. On the other hand, cyano-stilbene-based probes are also well known for their good mechanofluorochromic [47], thermochromic [48], and piezochromic [49] behaviors in their condensed state. As both the probes, AIE-1 and AIE-2, contain donor and acceptor units in their molecular structure, the emission enhancement of AIE-2 can be attributed to the formation of aggregates with a stabilized ICT effect in high water fractions [50].…”

Section: Aggregation Study By Uv-vis and Fluorescence Spectroscopymentioning

confidence: 99%

ICT and AIE Characteristics Two Cyano-Functionalized Probes and Their Photophysical Properties, DFT Calculations, Cytotoxicity, and Cell Imaging Applications

et al. 2020

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Two probes, AIE-1 and AIE-2, were synthesized to investigate the effect of substitutional functional group on aggregation (aggregation-caused quenching (ACQ) or aggregation-induced emission (AIE)) and intramolecular charge transfer (ICT) behavior as well as on the cell imaging aspect. The yellow-color non-substituted probe AIE-1 showed weak charge-transfer absorption and an emission band at 377 nm and 432 nm, whereas the yellowish-orange color substituted probe AIE-2 showed a strong charge-transfer absorption and an emission band at 424 nm and 477 nm in THF solvent. The UV-Vis studies of AIE-1 and AIE-2 in THF and THF with different water fractions showed huge absorption changes in AIE-2 with high water fractions due to its strong aggregation behavior, but no such noticeable absorption changes were observed for AIE-1. Interestingly, the fluorescence intensity of AIE-1 at 432 nm gradually decreased with increasing water fractions and became almost non-emissive at 90% water. However, the monomer-type emission of AIE-2 at 477 nm was shifted to 584 nm with a 6-fold increase in fluorescence intensity in THF-H2O (1:9, v/v) solvent mixtures due to the restriction of intramolecular rotation on aggregation in high water fractions. This result indicates that the probe AIE-1 shows ACQ and probe AIE-2 shows AIE behaviors in THF-H2O solvent mixtures. Furthermore, the emission spectra of AIE-1 and AIE-2 were carried out in different solvent and with different concentrations to see the solvent- or concentration-dependent aggregation behavior. Scanning electron microscope (SEM) and dynamic light scattering (DLS) experiments were also conducted to assess the morphology and particle size of two probes before and after aggregation. Both of the probes, AIE-1 and AIE-2, showed less toxicity on HeLa cells and were suitable for cell imaging studies. Density functional theory (DFT) calculation was also carried out to confirm the ICT process from an electron-rich indole moiety to an electron-deficient cyano-phenyl ring of AIE-1 or AIE-2.

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“…Trans-aminostilbenes are a class of p-donor-acceptor (D-A) systems that have been investigated as fluorescent probes [1][2][3][4][5][6], cell imaging dyes [7][8][9], and the active materials in a variety of optoelectronic devices such as organic light-emitting diodes [10,11], dye-sensitized solar cells [12][13][14], nonlinear optics [15][16][17][18][19][20], and molecular switches [21,22]. These applications are all associated with the electronically excited states, in which the lowest singlet excited state (S 1 ) possesses a significant degree of charge separation as a result of intramolecular charge-transfer (ICT) from the amino to the stilbene moiety upon photoexcitation.…”

Section: Introductionmentioning

confidence: 99%

Fate of photoexcited trans-aminostilbenes

Yang

Lin

2015

Journal of Photochemistry and Photobiology A: Chemistry

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Mechanochromic and thermochromic fluorescent properties of cyanostilbene derivatives

Cited by 77 publications

References 32 publications

Efficient piezochromic luminescence from tetraphenylethene functionalized pyridine-azole derivatives exhibiting aggregation-induced emission

Efficient piezochromic luminescence from tetraphenylethene functionalized pyridine-azole derivatives exhibiting aggregation-induced emission

ICT and AIE Characteristics Two Cyano-Functionalized Probes and Their Photophysical Properties, DFT Calculations, Cytotoxicity, and Cell Imaging Applications

Fate of photoexcited trans-aminostilbenes

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