Finely regulated benzothiadiazole derivatives: Aggregation-induced emission (AIE), hypso- or bathochromic mechanofluorochromic behaviors, and multilevel information encryption applications

Deng, Diandian; Zou, Yixin; Chen, Zhao; Liu, Shanting; Yang, Yue; Pu, Shouzhi

doi:10.1016/j.dyepig.2022.111051

Cited by 12 publications

(7 citation statements)

References 50 publications

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“…[25][26] The emission intensity of 2-Pyr-ROF was roughly 20 times that of DMSO (Figures 2c and 2d), demonstrating a spectacular AIE phenomena. [27] Similarly, the experimental results confirmed that 2-Pip-ROF also showed an obvious AIE phenomenon. Meanwhile, as shown in Figure 2e, 2-Pip-ROF displayed slightly different AIE behavior.…”

Section: Photoluminescence (Pl) In the Aggregated Statesupporting

confidence: 58%

“…The emission peak of 2‐Pyr‐ROF redshifted from 590 nm to 650 nm when the water percentage was increased to 99 %( Φ F =2.7 %), indicating the creation of J ‐aggregates and the rapid enhancement of the rigidity [25–26] . The emission intensity of 2‐Pyr‐ROF was roughly 20 times that of DMSO (Figures 2c and 2d), demonstrating a spectacular AIE phenomena [27] . Similarly, the experimental results confirmed that 2‐Pip‐ROF also showed an obvious AIE phenomenon.…”

Section: Resultsmentioning

confidence: 94%

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Effects of a Larger N‐Heterocyclic Ring in Rofecoxib Analogues on AIE Activity and Multifunctional Applications

Liu,

Yao,

et al. 2024

Eur J Org Chem

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Two analogues of rofecoxib, 2‐Pyr‐ROF and 2‐Pip‐ROF, were designed according to the strategy of heterocyclic ring enlargement and facilely synthesized in a facile manner by Knoevenagel reactions. The first compound, 2‐Pyr‐ROF, had low quantum yields (QY) of 3.0% in the solid states. After replacing the pyrrolidinyl with piperidinyl, the resulting 2‐Pip‐ROF had a significantly increased QY, with a value of 28%. The root‐mean‐square deviation (RMSD) values between S0 and S1 of 2‐Pyr‐ROF and 2‐Pip‐ROF in tetrahydrofuran were 0.51, 0.35 Å, respectively. As compared with 2‐Pyr‐ROF, compound 2‐Pip‐ROF exhibits a smaller RMSD, which indicates a lower non‐radiative transition rate. A single‐crystal X‐ray diffraction study and Hirshfeld surfaces analysis revealed that 2‐Pip‐ROF had a more nonplanar molecule structure and a weaker π‐π interaction, which might result in a higher fluorescence intensity and QY. Owing to its better aggregation‐induced emission (AIE) behavior, compound 2‐Pip‐ROF showed more multi‐functional applications, including mechanochromism, acidochromism, and lipid droplets imaging ability. These results imply that the strategy of heterocyclic ring enlargement provides a new paradigm for the design of new luminogens with AIE properties.

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Section: Photoluminescence (Pl) In the Aggregated Statesupporting

confidence: 58%

Section: Resultsmentioning

confidence: 94%

Effects of a Larger N‐Heterocyclic Ring in Rofecoxib Analogues on AIE Activity and Multifunctional Applications

Liu,

Yao,

et al. 2024

Eur J Org Chem

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“…In the past decade, the rapid development of the stimuliresponsive fluorescent materials with the obvious changes of fluorescent emission wavelength or luminescence color had received a great deal of interests in the fields of optical rewritable storage papers, [1] organic light-emitting diodes, [2] fluorescent sensors, [3] and photoswitches. [4] At present, the mechanofluorochromic (MFC) materials as one of the stimuliresponsive fluorescent materials had been widely reported, [5][6][7][8] for example, the derivatives of benzo [d]imidazole, [9] dicyanovinyl, [10] bisarylic methanone, [11] [1]Benzothieno [3,2b] [1]benzothiophene, [12] isoquinoline, [13] indolo [3,2b]carbazole, [14] and micelle-hydrogel composites [15] etc. It was remarkable that these materials had aggregation-induced emission (AIE) behaviors.…”

Section: Introductionmentioning

confidence: 99%

Reversible Red‐/Blue‐Shifted Mechanofluorochromic Properties of Indole‐Based Difluoroboron Compounds with Aggregation‐Induced Emission

Xu,

Zhang,

Tian

et al. 2024

ChemistrySelect

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To further explore the relationship between structure and property of the mechanofluorochromic materials, two indole‐based aggregation‐induced emission compounds (I−Ph−BF2 and I−PhNp−BF2) with BF2‐core were designed and synthesized. They displayed intramolecular charge transfer characteristics and dissimilar reversible mechanofluorochromic behaviors (red‐shift for I−Ph−BF2 and blue‐shift for I−PhNp−BF2). Based the powder X‐ray diffraction patterns and quantum chemical calculation results, it was responsible for the blue‐shift mechanofluorochromic behavior of I−PhNp−BF2 that the reduced molecular polarity of the excited state and the undermined partially ordered structure. In contrast, the phase change between an ordered arrangement state and a disordered amorphous state of I−Ph−BF2 solid powder, as well as the appropriate molecular polarity, brought out red‐shift mechanofluorochromic effect. It provided a foundation for further exploration of the mechanofluorochromic property.

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“…2 of 18 state of molecules, a problem of the utmost importance for many scientific fields or technological applications. [4,7,8] Among the many areas taking advantage of AIEgens, we can mention optoelectronics with OLEDs, [9,10] stimuli-responsive materials, [11][12][13] anticounterfeiting or encryption, [12,14] sensing, [15][16][17] and biology or medicine, fields in which the use of AIEgens has enabled spectacular advances. [18][19][20][21][22][23] Indeed, AIEs are used in the fields of imaging, [24,25] elucidation of biological processes, [26][27][28] innovative therapies such as photodynamic therapy (PDT), [29][30][31] photothermal therapy (PTT), [32,33] sonodynamic therapy enhancement, [34] cocktail therapy [35] and theranostics.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Tetraphenylethene AIEgen-Based Push-Pull Chromophores for Photothermal Applications: Do the Cycloaddition – Retroelectrocyclization Click Reaction Could Make any Molecule Photothermally Active?

Roger¹,

Bretonnière²,

Trolez³

et al. 2023

Preprint

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Three new tetraphenylethene (TPE) push-pull chromophores exhibiting strong intramolecular charge transfer (ICT) are described. They were obtained via [2+2] cycloaddition - retroelectrocyclization (CA-RE) click reactions on an electron-rich alkyne-tetrafunctionalized TPE (TPE-alkyne) using both 1,1,2,2-tetracyanoethene (TCNE), 7,7,8,8-tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) as electron-deficient alkene. Only the starting TPE-alkyne displayed a significant AIE behavior, whereas for TPE-TCNE,a faint effect was observed and for TPE-TCNQ and TPE-F4-TCNQ, no fluorescence was observed in any conditions. The main ICT bands that dominate the UV-Visible absorption spectra underwent a pronounced red-shift beyond the near-infrared (NIR) region for TPE-F4-TCNQ. Based on TD-DFT calculations, it was shown that the ICT character shown by the compounds exclusively originated from the clicked moieties independently of the nature of the central molecular platform. Photothermal (PT) studies conducted on both TPE-TCNQ and TPE-F4-TCNQ in the solid state revealed excellent properties, especially for TPE-F4-TCNQ. These results indicated that CA-RE reaction of TCNQ or F4-TCNQ with donor-substituted are promising candidates for PT applications.

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Finely regulated benzothiadiazole derivatives: Aggregation-induced emission (AIE), hypso- or bathochromic mechanofluorochromic behaviors, and multilevel information encryption applications

Cited by 12 publications

References 50 publications

Effects of a Larger N‐Heterocyclic Ring in Rofecoxib Analogues on AIE Activity and Multifunctional Applications

Effects of a Larger N‐Heterocyclic Ring in Rofecoxib Analogues on AIE Activity and Multifunctional Applications

Reversible Red‐/Blue‐Shifted Mechanofluorochromic Properties of Indole‐Based Difluoroboron Compounds with Aggregation‐Induced Emission

Synthesis and Characterization of Tetraphenylethene AIEgen-Based Push-Pull Chromophores for Photothermal Applications: Do the Cycloaddition – Retroelectrocyclization Click Reaction Could Make any Molecule Photothermally Active?

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