Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens

Qi, Ji; Duan, Xingchen; Cai, Yuanjing; Jia, Shaorui; Chen, Chao; Zhao, Zheng; Liu, Ying; Peng, Hui‐Qing; Kwok, Ryan T. K.; Lam, Jacky W. Y.; Ding, Dan; Tang, Ben Zhong

doi:10.1039/d0sc03423a

Cited by 33 publications

(20 citation statements)

References 57 publications

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“…The thieno[3,4‐ b ]pyrazine core is a relevant and versatile acceptor moiety in the synthesis of D−A−D molecules: i ) its electron deficiency and poor aromaticity impart a high ICT character to the dye excited state, resulting in a deeply red‐shifted absorption and emission bands; ii ) importantly, judicious functionalization of the acceptor core enables additional tuning of the dye photophysical properties [10] . While these unique features have enabled the preparation of efficient organic NIR luminophores, the use of thieno[3,4‐ b ]pyrazine in the development of NIR emitters with AIE properties has remained poorly investigated [11] …”

Section: Introductionmentioning

confidence: 99%

Donor‐Acceptor‐Donor Thienopyrazine‐Based Dyes as NIR‐Emitting AIEgens

et al. 2021

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Organic Near‐Infrared luminophores have found broad application as functional materials, but the development of efficient NIR emitters is still a challenging goal. Here we report on a new class of thieno[3,4‐b]pyrazine‐based NIR emitting materials with Aggregation Induced Emission (AIE) properties. The dyes feature a donor–acceptor–donor (D−A−D) structure, with a thienopyrazine acceptor core connected to two triarylamine donor groups bearing a tetraphenylethylene (TPE) moiety. Fast and efficient synthesis allowed the modular preparation of three dyes of tunable absorption and emission profiles. These constructs were extensively characterized by spectroscopic studies in different solvents, which revealed intense light‐harvesting ability and emissions in the deep‐red and NIR region with large Stokes shift values. Remarkably, the dyes exhibited AIE properties, retaining emissive ability in the aggregate state, thus emerging as attractive materials for their potential application in the development of luminescent devices.

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Section: Introductionmentioning

confidence: 99%

Donor‐Acceptor‐Donor Thienopyrazine‐Based Dyes as NIR‐Emitting AIEgens

et al. 2021

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“…In 2010, Shimizu and Hiyama expressed an essential requirement to obtain red fluorophores with PLQY over 30 % from neat solids and fulfilled it in 2012 for first time with the observed emission with a maximum over 700 nm (702 nm) and PLQY over 30 % (33 %) at the same time [11] . Although, since then, the impressive values of NIR emission have been reported for polycrystalline powders (for example, 735 nm/11 %), [9b] water dispersions of nanoparticles (for example, 685 nm/20.7 %), [12] and neat films (for example, 756 nm/17 % [13] or 750 nm/21 %), [14] the >700 nm/>30 % limit still remains a challenge [15] . There are generally two ways to tune the position of emission maxima.…”

Section: Introductionmentioning

confidence: 99%

Green‐, Red‐, and Infrared‐Emitting Polymorphs of Sterically Hindered Push–Pull Substituted Stilbenes

Pauk

Luňák

Růžička

et al. 2020

Chemistry A European J

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The synthesis, XRD single‐crystal structure, powder XRD, and solid‐state fluorescence of two new DPA‐DPS‐EWG derivatives (DPA=diphenylamino, DPS=2,5‐diphenyl‐stilbene, EWG=electron‐withdrawing group, that is, carbaldehyde or dicyanovinylene, DCV) are described. Absorption and fluorescence maxima in solvents of various polarity show bathochromic shifts with respect to the parent DPA‐stilbene‐EWGs. The electronic coupling in dimers and potential twist elasticity of monomers were studied by density functional theory. Both polymorphs of the CHO derivative emit green fluorescence (527 and 550 nm) of moderate intensity (10 % and 5 %) in polycrystalline powder form. Moderate (5 %) red (672 nm) monomer‐like emission was also observed for the first polymorph of the DCV derivative, whereas more intense (32 %) infrared (733 nm) emission of the second polymorph was ascribed to the excimer fluorescence.

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“…The lifetime ( τ ) increased from TPA‐TQ1 NPs to TPA‐TQ3 NPs, which was in the same trend as PLQY (Figure 3 f). The fluorescence properties were closely related to the radiative and non‐radiative decay rates ( k r and k nr ) [57–59] . According to the equations: τ =1/( k r + k nr ), Φ F = k r /( k r + k nr ), the k r / k nr values of TPA‐TQ1‐3 NPs were calculated to be 0.136/9.57×10 8 , 0.215/5.31×10 8 and 0.287/3.93×10 8 s −1 (Table S1), respectively.…”

Section: Resultsmentioning

confidence: 99%

Boosting Photoacoustic Effect via Intramolecular Motions Amplifying Thermal‐to‐Acoustic Conversion Efficiency for Adaptive Image‐Guided Cancer Surgery

et al. 2021

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Photoacoustic (PA) imaging emerges as a promising technique for biomedical applications. The development of new strategies to boost PA conversion without depressing other properties (e.g., fluorescence) is highly desirable for multifunctional imaging but difficult to realize. Here, we report a new phenomenon that active intramolecular motions could promote PA signal by specifically increasing thermal‐to‐acoustic conversion efficiency. The compound with intense intramolecular motion exhibits amplified PA signal by elevating thermal‐to‐acoustic conversion, and the fluorescence also increases due to aggregation‐induced emission signature. The simultaneously high PA and fluorescence brightness of TPA‐TQ3 NPs enable precise image‐guided surgery. The preoperative fluorescence and PA imaging are capable of locating orthotopic breast tumor in a high‐contrast manner, and the intraoperative fluorescence imaging delineates tiny residual tumors. This study highlights a new design guideline of intramolecular motion amplifying PA effect.

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Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens

Abstract: AIEgens are exploited to simultaneously extend the conjugation, boost the brightness, and increase the solubility of organic near-infrared fluorophores, representing a new strategy for developing high-performance emitters for biomedical imaging.

Cited by 33 publications

References 57 publications

Donor‐Acceptor‐Donor Thienopyrazine‐Based Dyes as NIR‐Emitting AIEgens

Donor‐Acceptor‐Donor Thienopyrazine‐Based Dyes as NIR‐Emitting AIEgens

Green‐, Red‐, and Infrared‐Emitting Polymorphs of Sterically Hindered Push–Pull Substituted Stilbenes

Boosting Photoacoustic Effect via Intramolecular Motions Amplifying Thermal‐to‐Acoustic Conversion Efficiency for Adaptive Image‐Guided Cancer Surgery

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