Red/NIR‐Emissive Benzo[d]imidazole‐Cored AIEgens: Facile Molecular Design for Wavelength Extending and In Vivo Tumor Metabolic Imaging

Aggregation‐induced emission (AIE) luminogens (AIEgens) with red/near‐infrared (NIR) emissions are appealing for applications in optoelectronics and biomedical engineering owing to their intrinsic advantages of efficient solid‐state emission, low background, and deep tissue penetration. In this cont...

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Published in:Advanced materials (Weinheim) 2018-12, Vol.30 (50), p.e1805220-n/a
Main Authors: Ni, Jen‐Shyang, Zhang, Pengfei, Jiang, Tao, Chen, Yuncong, Su, Huifang, Wang, Dong, Yu, Zhen‐Qiang, Kwok, Ryan T. K., Zhao, Zujin, Lam, Jacky W. Y., Tang, Ben Zhong
Format: Article
Language:English
Subjects:
Acetonitrile
aggregation‐induced emission
Biomedical engineering
Biomedical materials
Chemical synthesis
click reaction
Conjugation
Cyclohexane
donor–acceptor
Emission
Fluorescence
Imidazole
in vivo metabolic labeling
Materials science
Metabolism
Molecular structure
near‐infrared
Optoelectronics
Organic chemistry
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Summary:Aggregation‐induced emission (AIE) luminogens (AIEgens) with red/near‐infrared (NIR) emissions are appealing for applications in optoelectronics and biomedical engineering owing to their intrinsic advantages of efficient solid‐state emission, low background, and deep tissue penetration. In this context, an AIEgen with long‐wavelength emission is synthesized by introducing tetraphenylethene (TPE) to the periphery of electron‐deficient spiro‐benzo[d]imidazole‐2,1′‐cyclohexane (BI). The resulting AIEgen, abbreviated as 2TPE‐BI, adopts a donor–acceptor structure and shows bathochromic absorption and emission with a larger Stokes shift of 157 nm in acetonitrile than that based on benzo[c][1,2,5]thiadiazole. It also exhibits a high solid‐state fluorescence quantum yield of 56.6%. By further insertion of thiophene to its molecular structure generates 2TPE‐2T‐BI with higher conjugation and NIR emission. 2TPE‐2T‐BI can be fabricated into AIE dots for in vivo metabolic labeling through bio‐orthogonal click chemistry. These results open a new approach for facile construction of long‐wavelength emissive AIEgens based on the BI core. A new strategy for designing red/near‐infrared aggregation‐induced‐emission luminogens by introducing the electron‐deficient and antipacking spiro‐cyclohexyl‐substituted benzo[d]imidazole core is promoted. The further application to in vivo special expression on the surface of tumor tissue is achieved through the combination of metabolic glycoengineering and bio‐orthogonal copper‐free click chemistry.
ISSN:0935-9648
1521-4095
DOI:10.1002/adma.201805220