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Novel butterfly-shaped AIE-active pyrrolopyrrole aza-BODIPYs: synthesis, bioimaging and diamine/polyamine detection

文献类型： 外文期刊

作者： Li, Wenting 1 ; Wang, Lingyun 1 ; Zhang, Chufeng 1 ; Ran, Xueguang 2 ; Tang, Hao 1 ; Cao, Derong 1 ;

作者机构： 1.South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, 381 Wushan Rd, Guangzhou 510641, Peoples R China

2.Guangdong Acad Agr Sci, State Key Lab Livestock & Poultry Breeding, Key Lab Anim Nutr & Feed Sci South China, Minist Agr,Inst Anim Sci, Guangzhou 510641, Peoples R China

期刊名称：JOURNAL OF MATERIALS CHEMISTRY C （ 影响因子：8.067； 五年影响因子：7.642 ）

ISSN： 2050-7526

年卷期： 2022 年 10 卷 14 期

页码：

收录情况： SCI

摘要： Constructing novel near-infrared (NIR) fluorophores with an aggregation-induced emission (AIE) character is of particular interest but remains challenging. In this work, we linked two propeller-shaped alkoxyl-substituted tetraphenylethylene (TPE) to the short axis of a pyrrolopyrrole aza-BODIPY (PPAB) core by a phenylene spacer to form three novel NIR dyes (PPAB-TPE1-PPAB-TPE3). Due to the butterfly-shaped conformation and non-planar molecular structure, three dyes exhibited typical AIE characteristics with up to 390-fold fluorescence enhancement in the aggregated state. The structural effects on their photophysical properties and solvatochromic behavior via experimental and theoretical approaches were studied. The results indicated that attaching an AIE rotor along the short axis of PPAB is an efficient and facile strategy to construct AIE-active NIR dyes. Taking PPAB-TPE1 as an example, the resulting nanoparticles encapsulated by an amphiphilic copolymer F-127 had a small size and NIR emission, which showed potential application to bioimaging in HeLa cells. Moreover, PPAB-TPE1 showed sensitive and selective detection of diamine/polyamine with an over 210 nm hypsochromic shift in the absorption maximum and ratiometric fluorescence "turn on" process. The limit of detection was up to 0.053 mu M. Visual putrescine gas detection with colorimetric and ratiometric fluorescent modes was also demonstrated.

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