The abnormal solvatochromism, high-contrast mechanochromism and internal mechanism of two AIEE-active β-diketones

Liu, Wenjing; Wang, Yongtao; Yang, Jinfeng; Li, Xueming; Wang, Xiaojuan; Ma, Lei

doi:10.1016/j.dyepig.2019.108149

Cited by 21 publications

(4 citation statements)

References 29 publications

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“…The rotating units (Ph groups) of this structure are able to rotate in diluted solutions and, therefore, a nonemissive pathway is the preferential relaxation process. When the aggregation takes place, these molecular motions are blocked by intermolecular interactions and the emission from a radioactive pathway is favored, as confirmed for several small organic molecules and derivatives with the AIE effect. − After these findings, aggregation-induced emission enhancement (AIEE) luminophores were brought to a prominent position among small organic molecules. − The enhancement of light emissions upon aggregation may also afford bathochromic or hypsochromic shifts, thus allowing the color tuning for specific applications.…”

Section: Introductionmentioning

confidence: 90%

Deciphering the Dynamics of Organic Nanoaggregates with AIEE Effect and Excited States: Lipophilic Benzothiadiazole Derivatives as Selective Cell Imaging Probes

Sodre

Guido

Souza³

et al. 2020

J. Org. Chem.

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An aggregation-induced emission enhancement (AIEE) effect in fluorescent lipophilic 2,1,3-benzothiadiazole (BTD) derivatives and their organic nanoaggregates were studied. A set of techniques such as single-crystal X-ray, dynamic light scattering (DLS), electron paramagnetic resonance (EPR), UV−vis, fluorescence, and density functional theory (DFT) calculations have been used to decipher the formation/break (kinetics), properties, and dynamics of the organic nanoaggregates of three BTD small organic molecules. An in-depth study of the excited-state also revealed the preferential relaxation emissive pathways for the BTD derivatives and the dynamics associated with it. The results described herein, for the first time, explain the formation of fluorescent BTD nanoaggregate derivatives and allow for the understanding of their dynamics in solution as well as the ruling forces of both aggregation and break processes along with the involved equilibrium. One of the developed dyes could be used at a nanomolar concentration to selectively stain lipid droplets emitting an intense and bright fluorescence at the red channel. The other two BTDs could also stain lipid droplets at very low concentrations and were visualized preferentially at the blue channel.

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Section: Introductionmentioning

confidence: 90%

Deciphering the Dynamics of Organic Nanoaggregates with AIEE Effect and Excited States: Lipophilic Benzothiadiazole Derivatives as Selective Cell Imaging Probes

Sodre

Guido

Souza³

et al. 2020

J. Org. Chem.

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“…The exothermic peak should be attributed to the phase transition from the yellow-emissive cystalline state to another amorphous state with red emission. [45] Consequently, 2-Pip-ROF will be a viable option for the creation of a new and effective MCL material.…”

Section: Single-crystal Structure Analysismentioning

confidence: 99%

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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“…24,25 In addition, solid state luminescence studies showed that many BDK compounds present mechanochromic properties, their emission wavelength being correlated to their solid structure. [26][27][28][29][30][31][32][33][34][35][36][37] BDK compounds, in solid state, were also applied for the detection of volatile amines because these latter can interact with difluoroboron moiety, lowering their acceptor character, leading to blue shifted emission and increase of fluorescence quantum yields. [38][39][40] The development of synthetic methods producing unsymmetrical β-diketone compounds can give access to push pull chromophores i.e.…”

Section: Introductionmentioning

confidence: 99%

Unsymmetrical boron diketonates containing strong electron-donating groups as mechanochromic fluorescent solids

et al. 2023

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The abnormal solvatochromism, high-contrast mechanochromism and internal mechanism of two AIEE-active β-diketones

Cited by 21 publications

References 29 publications

Deciphering the Dynamics of Organic Nanoaggregates with AIEE Effect and Excited States: Lipophilic Benzothiadiazole Derivatives as Selective Cell Imaging Probes

Deciphering the Dynamics of Organic Nanoaggregates with AIEE Effect and Excited States: Lipophilic Benzothiadiazole Derivatives as Selective Cell Imaging Probes

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

Unsymmetrical boron diketonates containing strong electron-donating groups as mechanochromic fluorescent solids

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