Achieving ACQ-AIE modulation using isostructural organic fluorophores

Pratihar, Swatilekha; Bhattacharyya, Ayan; Prasad, Edamana

doi:10.1016/j.jphotochem.2020.112458

“…Prasad et al. regulated the structure of isomers to realize the ACQ‐to‐AIE transformation, owing to the absence of interplay between the excited states . These insightful strategies inspire new ideas for regulating solid‐state fluorescence.…”

Section: Figurementioning

confidence: 99%

ACQ‐to‐AIE Transformation: Tuning Molecular Packing by Regioisomerization for Two‐Photon NIR Bioimaging

Li

¹

,

Liu

²

,

Ni

³

et al. 2020

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The traditional design strategies for highly bright solid‐state luminescent materials rely on weakening the intermolecular π–π interactions, which may limit diversity when developing new materials. Herein, we propose a strategy of tuning the molecular packing mode by regioisomerization to regulate the solid‐state fluorescence. TBP‐e‐TPA with a molecular rotor in the end position of a planar core adopts a long‐range cofacial packing mode, which in the solid state is almost non‐emissive. By shifting molecular rotors to the bay position, the resultant TBP‐b‐TPA possesses a discrete cross packing mode, giving a quantum yield of 15.6±0.2 %. These results demonstrate the relationship between the solid‐state fluorescence efficiency and the molecule's packing mode. Thanks to the good photophysical properties, TBP‐b‐TPA nanoparticles were used for two‐photon deep brain imaging. This molecular design philosophy provides a new way of designing highly bright solid‐state fluorophores.

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“…The same strategy was utilized by Xu’s group to achieve ACQ-to-AIE conversion through changing the substituted position of a benzanthrone moiety from the meta-position to the ortho -position on the perylenetetracarboxylic diimide core ( Long et al, 2021 ). Similarly, Prasad’s group also realized ACQ-to-AIE transformation by changing a cyano group from the para -position to the meta-position on the same phenyl group ( Pratihar et al, 2020 ). Despite the great examples above, the successful cases of the regioisomerization of small units are still rare ( Pratihar et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

“…Similarly, Prasad’s group also realized ACQ-to-AIE transformation by changing a cyano group from the para -position to the meta-position on the same phenyl group ( Pratihar et al, 2020 ). Despite the great examples above, the successful cases of the regioisomerization of small units are still rare ( Pratihar et al, 2020 ). Therefore, it is still necessary to develop more examples of ACQ-to-AIE conversion to guide the design of novel AIEgen materials.…”

Section: Introductionmentioning

confidence: 99%

“…Modification of the existing AIE scaffolds is the most popular strategy for constructing new AIEgens (Mei et al, 2015). In addition to this strategy, transforming ACQ molecules into AIE-active materials also provides a direct way to design highly bright AIEgens due to the rich source of ACQ (Yuan et al, 2010;Zong et al, 2016;Liu et al, 2017;Lu et al, 2019;Li Y. et al, 2020;Pratihar et al, 2020;Wang et al, 2020;Huang et al, 2021;Long et al, 2021;Zhang et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Precise Molecular Design of a Pair of New Regioisomerized Fluorophores With Opposite Fluorescent Properties

Wang

¹

,

Li

²

,

Chen

³

et al. 2022

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Aggregation-induced emission (AIE) has attracted much attention in the past 2 decades. To develop novel AIE-active materials, ACQ-to-AIE transformation via regioisomerization is one of the most straightforward method. However, most of the reported ACQ-to-AIE transformations are achieved by migrating bulky units. In this work, a facile conversion was realized by migrating a small pyrrolidinyl group from para- to ortho-position on the rofecoxib scaffold. As a result, a pair of new isomers named MOX2 and MOX4 exhibited AIE behavior and ACQ activity, respectively. Moreover, MOX2 also showed solvatochromic, mechanochromic, and acidochromic properties with reversible multi-stimulus behavior. Single crystal X-ray analysis of MOX2 revealed that the molecular conformation and its packing mode were responsible for the AIE emission behavior. Further investigation indicated that MOX2 showed high lipid droplets staining selectivity. Taken together, the current work not only provides a new design philosophy for achieving ACQ-to-AIE conversion by migrating a small pyrrolidinyl group but also presents a promising candidate MOX2 for potential applications such as in security ink, optical recording and biological applications.

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“…Prasad et al regulated the structure of isomers to realize the ACQ-to-AIE transformation, owing to the absence of interplay between the excited states. [11] These insightful strategies inspire new ideas for regulating solidstate fluorescence. However, the molecular packing mode remains vague, posing a challenge for further understanding the solid-state fluorescence property.…”

mentioning

confidence: 99%

ACQ‐to‐AIE Transformation: Tuning Molecular Packing by Regioisomerization for Two‐Photon NIR Bioimaging

Li

¹

,

Liu

²

,

Ni

³

et al. 2020

View full text Add to dashboard Cite

The traditional design strategies for highly bright solid‐state luminescent materials rely on weakening the intermolecular π–π interactions, which may limit diversity when developing new materials. Herein, we propose a strategy of tuning the molecular packing mode by regioisomerization to regulate the solid‐state fluorescence. TBP‐e‐TPA with a molecular rotor in the end position of a planar core adopts a long‐range cofacial packing mode, which in the solid state is almost non‐emissive. By shifting molecular rotors to the bay position, the resultant TBP‐b‐TPA possesses a discrete cross packing mode, giving a quantum yield of 15.6±0.2 %. These results demonstrate the relationship between the solid‐state fluorescence efficiency and the molecule's packing mode. Thanks to the good photophysical properties, TBP‐b‐TPA nanoparticles were used for two‐photon deep brain imaging. This molecular design philosophy provides a new way of designing highly bright solid‐state fluorophores.

show abstract

Achieving ACQ-AIE modulation using isostructural organic fluorophores

Cited by 31 publications

References 53 publications

ACQ‐to‐AIE Transformation: Tuning Molecular Packing by Regioisomerization for Two‐Photon NIR Bioimaging

ACQ‐to‐AIE Transformation: Tuning Molecular Packing by Regioisomerization for Two‐Photon NIR Bioimaging

Precise Molecular Design of a Pair of New Regioisomerized Fluorophores With Opposite Fluorescent Properties

ACQ‐to‐AIE Transformation: Tuning Molecular Packing by Regioisomerization for Two‐Photon NIR Bioimaging

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