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Red/NIR‐Emissive Benzo[d]imidazole‐Cored AIEgens: Facile Molecular Design for Wavelength Extending and In Vivo Tumor Metabolic Imaging
Advanced Materials ( IF 29.4 ) Pub Date : 2018-10-15 , DOI: 10.1002/adma.201805220
Jen‐Shyang Ni 1 , Pengfei Zhang 1, 2, 3 , Tao Jiang 3 , Yuncong Chen 1, 2 , Huifang Su 1, 2 , Dong Wang 4 , Zhen‐Qiang Yu 4 , Ryan T. K. Kwok 1, 2 , Zujin Zhao 5 , Jacky W. Y. Lam 1, 2 , Ben Zhong Tang 1, 2, 5
Affiliation  

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.

中文翻译:

红色/近红外发射苯并[d]咪唑类AIEgens:用于波长扩展和体内肿瘤代谢成像的简便分子设计

具有聚集红色/近红外(NIR)辐射的聚集诱导发射(AIEgens)发光体(AIEgens)由于其有效的固态发射,低背景和深层组织渗透的固有优势而吸引了其在光电子和生物医学工程中的应用。在这种情况下,通过在缺乏电子的-苯并[ d ]咪唑-2,1'-环己烷(BI)的周围引入四苯乙烯(TPE)来合成具有长波长发射的AIEgen 。所得的AIEgen(缩写为2TPE-BI)采用供体-受体结构,并显示出红移吸收和发射,乙腈中的斯托克斯位移比基于苯并[ a]的更大,斯托克斯位移为157 nm。] [1,2,5]噻二唑。它还具有56.6%的高固态荧光量子产率。通过进一步将噻吩插入其分子结构,可产生具有更高共轭和近红外发射的2TPE-2T-BI。可以将2TPE-2T-BI制成AIE点,以通过生物正交点击化学进行体内代谢标记。这些结果为基于BI核的长波发射AIEgen的简便构建开辟了一种新方法。
更新日期:2018-10-15
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