Bright solid-state red-emissive BODIPYs: facile synthesis and their high-contrast mechanochromic properties

Duan, Chong; Zhou, Yibin; Shan, Guo‐Gang; Chen, Yuncong; Zhao, Weijun; Yuan, Dandan; Zeng, Lintao; Huang, Xiaobo; Niu, Guangle

doi:10.1039/c8tc06421k

Cited by 89 publications

(55 citation statements)

References 68 publications

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“…2d and S19b †). 46 The MeO-BOD NPs could be disassembled and the instinctive uorescence peak of MeO-BOD could be restored in the presence of FBS (10%) in DW (Fig. S19 †).…”

Section: Cellular Uorescence Imaging and Subcellular Colocalizationmentioning

confidence: 99%

Fine-tuning the electronic structure of heavy-atom-free BODIPY photosensitizers for fluorescence imaging and mitochondria-targeted photodynamic therapy

et al. 2020

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“…2d and S19b †). 46 The MeO-BOD NPs could be disassembled and the instinctive uorescence peak of MeO-BOD could be restored in the presence of FBS (10%) in DW (Fig. S19 †).…”

Section: Cellular Uorescence Imaging and Subcellular Colocalizationmentioning

confidence: 99%

Fine-tuning the electronic structure of heavy-atom-free BODIPY photosensitizers for fluorescence imaging and mitochondria-targeted photodynamic therapy

et al. 2020

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“…27 The distances between the borondipyrrole plane are ~ 3.7 Å. Ph-BDP1 show different molecular packing mode comparing to PCP-BDP1. 51 As shown in Figure S2, Ph-BDP1 molecules are arranged in a zigzag pattern through weak C-H⋅⋅⋅π interactions and no J-dimers were observed in the molecular packing structure. This difference demonstrates that the PCP group plays a key role in tuning the J-aggregation of BODIPY core.…”

Section: Resultsmentioning

confidence: 95%

J-Aggregates of meso- [2.2] Paracyclophanyl-BODIPY Dye for NIR-II Imaging

Liu

Duan

et al. 2020

Preprint

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J-aggregation has been proved to be an efficient strategy for the development of fluorescent imaging agents in the second near-infrared (NIR-II, 1000–1700 nm) window. However, the design of NIR-II fluorescent J-aggregates is challenging due to the lack of suitable J-aggregation dyes. Herein, we report meso-[2.2]paracyclophanyl-3,5-bis-N,N-dimethylaminostyrl BODIPY (PCP-BDP2) as the first example of BODIPY dye with J-aggregation induced NIR-II fluorescence. PCP-BDP2 shows emission maximum at 795 nm in diluted solution and NIR-II emission at 1010 nm in the J-aggregation state. Mechanism studies reveal that the steric and conjugation effect of the PCP group on the BODIPY core plays key roles in the J-aggregation behavior and NIR-II fluorescence tuning. Notably, NIR-II emissive J-aggregates of PCP-BDP2 can be efficiently stabilized in the assembled nanoparticle. Taking advantage of high quantum yield and good photo-/chemo-stability, J-aggregates of PCP-BDP2 show high-resolution and long-term in vivo NIR-II imaging ability. Furthermore, J-aggregates of PCP-BDP2 can be utilized for lymph node imaging and fluorescence-guided surgery in the nude mouse, which demonstrates their potential clinical application. This study not only demonstrates BODIPY dye as a new J-aggregation platform for developing NIR-II imaging agents but also encourages further exploration on J-aggregation induced NIR-II emission of the other conventional organic dyes.

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“…1 . Additionally, two BODIPY dyes, Ph-BDP1 51 and Ph-BDP2 54 , which have the phenyl group on the meso -position of the BODIPY core, were synthesized for comparison.…”

Section: Resultsmentioning

confidence: 99%

“…Notably, recent studies revealed that BODIPY dyes show potential to be employed as J-aggregation scaffolds. Many BODIPY dyes have been reported to be J-aggregated in lipid vesicles 38 – 43 , aqueous solution 44 – 48 , and crystalline state 49 – 51 . Moreover, several examples of BODIPY J-aggregates have been used for biological sensing and imaging.…”

Section: Introductionmentioning

confidence: 99%

J-aggregates of meso-[2.2]paracyclophanyl-BODIPY dye for NIR-II imaging

et al. 2021

Self Cite

View full text Add to dashboard Cite

J-aggregation is an efficient strategy for the development of fluorescent imaging agents in the second near-infrared window. However, the design of the second near-infrared fluorescent J-aggregates is challenging due to the lack of suitable J-aggregation dyes. Herein, we report meso-[2.2]paracyclophanyl-3,5-bis-N,N-dimethylaminostyrl BODIPY (PCP-BDP2) as an example of BODIPY dye with J-aggregation induced the second near-infrared fluorescence. PCP-BDP2 shows an emission maximum at 1010 nm in the J-aggregation state. Mechanism studies reveal that the steric and conjugation effect of the PCP group on the BODIPY play key roles in the J-aggregation behavior and photophysical properties tuning. Notably, PCP-BDP2 J-aggregates can be utilized for lymph node imaging and fluorescence-guided surgery in the nude mouse, which demonstrates their potential clinical application. This study demonstrates BODIPY dye as an alternate J-aggregation platform for developing the second near-infrared imaging agents.

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Bright solid-state red-emissive BODIPYs: facile synthesis and their high-contrast mechanochromic properties

Abstract: We first report several bright solid-state red-emissive BODIPYs with high fluorescence quantum yields for unusual high-contrast mechanohypsochromism.

Cited by 89 publications

References 68 publications

Fine-tuning the electronic structure of heavy-atom-free BODIPY photosensitizers for fluorescence imaging and mitochondria-targeted photodynamic therapy

Fine-tuning the electronic structure of heavy-atom-free BODIPY photosensitizers for fluorescence imaging and mitochondria-targeted photodynamic therapy

J-Aggregates of meso- [2.2] Paracyclophanyl-BODIPY Dye for NIR-II Imaging

J-aggregates of meso-[2.2]paracyclophanyl-BODIPY dye for NIR-II imaging

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