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Aggregation caused quenching to aggregation induced emission transformation: a precise tuning based on BN-doped polycyclic aromatic hydrocarbons toward subcellular organelle specific imaging
Chemical Science ( IF 7.6 ) Pub Date : 2022-02-11 , DOI: 10.1039/d2sc00380e Huanan Huang 1 , Lingxiu Liu 2 , Jianguo Wang 2 , Ying Zhou 1 , Huanan Hu 1 , Xinglin Ye 1 , Guochang Liu 1 , Zhixiong Xu 1 , Han Xu 1 , Wen Yang 1 , Yawei Wang 1 , You Peng 1 , Pinghua Yang 1 , Jianqi Sun 1 , Ping Yan 1 , Xiaohua Cao 1 , Ben Zhong Tang 3
Chemical Science ( IF 7.6 ) Pub Date : 2022-02-11 , DOI: 10.1039/d2sc00380e Huanan Huang 1 , Lingxiu Liu 2 , Jianguo Wang 2 , Ying Zhou 1 , Huanan Hu 1 , Xinglin Ye 1 , Guochang Liu 1 , Zhixiong Xu 1 , Han Xu 1 , Wen Yang 1 , Yawei Wang 1 , You Peng 1 , Pinghua Yang 1 , Jianqi Sun 1 , Ping Yan 1 , Xiaohua Cao 1 , Ben Zhong Tang 3
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Polycyclic aromatic hydrocarbons (PAHs) with boron–nitrogen (BN) moieties have attracted tremendous interest due to their intriguing electronic and optoelectronic properties. However, most of the BN-fused π-systems reported to date are difficult to modify and exhibit traditional aggregation-caused quenching (ACQ) characteristics. This phenomenon greatly limits their scope of application. Thus, continuing efforts to seek novel, structurally distinct and functionally diverse structures are highly desirable. Herein, we proposed a one-stone-two-birds strategy including simultaneous exploration of reactivity and tuning of the optical and electronic properties for BN-containing π-skeletons through flexible regioselective functionalization engineering. In this way, three novel functionalized BN luminogens (DPA-BN-BFT, MeO-DPA-BN-BFT and DMA-DPA-BN-BFT) with similar structures were obtained. Intriguingly, DPA-BN-BFT, MeO-DPA-BN-BFT and DMA-DPA-BN-BFT exhibit completely different emission behaviors. Fluorogens DPA-BN-BFT and MeO-DPA-BN-BFT exhibit a typical ACQ effect; in sharp contrast, DMA-DPA-BN-BFT possesses a prominent aggregation induced emission (AIE) effect. To the best of our knowledge, this is the first report to integrate ACQ and AIE properties into one BN aromatic backbone with subtle modified structures. Comprehensive analysis of the crystal structure and theoretical calculations reveal that relatively large twisting angles, multiple intermolecular interactions and tight crystal packing modes endow DMA-DPA-BN-BFT with strong AIE behavior. More importantly, cell imaging demonstrated that luminescent materials DPA-BN-BFT and DMA-DPA-BN-BFT can highly selectively and sensitively detect lipid droplets (LDs) in living MCF-7 cells. Overall, this work provides a new viewpoint of the rational design and synthesis of advanced BN–polycyclic aromatics with AIE features and triggers the discovery of new functions and properties of azaborine chemistry.
中文翻译：
聚集引起猝灭到聚集诱导发射转变：基于BN掺杂的多环芳烃对亚细胞细胞器特异性成像的精确调整
具有硼-氮（BN）部分的多环芳烃（PAHs）由于其有趣的电子和光电特性而引起了极大的兴趣。然而，迄今为止报道的大多数 BN 融合 π 系统难以修改并表现出传统的聚集引起的猝灭 (ACQ) 特性。这种现象极大地限制了它们的应用范围。因此，继续努力寻找新颖的、结构独特的和功能多样的结构是非常可取的。在这里，我们提出了一种一石二鸟的策略，包括通过灵活的区域选择性功能化工程同时探索反应性以及调整含 BN π 骨架的光学和电子特性。这样，三种新型功能化 BN 发光体（DPA-BN-BFT, MeO-DPA-BN-BFT和DMA-DPA-BN-BFT ) 具有相似的结构。有趣的是，DPA-BN-BFT、MeO-DPA-BN-BFT和DMA-DPA-BN-BFT表现出完全不同的发射行为。荧光剂 DPA-BN-BFT和MeO-DPA-BN-BFT表现出典型的 ACQ 效应；形成鲜明对比的是，DMA-DPA-BN-BFT具有显着的聚集诱导发射（AIE）效应。据我们所知，这是第一份将 ACQ 和 AIE 特性整合到一个具有细微修饰结构的 BN 芳族骨架中的报告。对晶体结构和理论计算的综合分析表明，较大的扭转角、多种分子间相互作用和紧密的晶体堆积模式赋予了DMA-DPA-BN-BFT较强的AIE行为。更重要的是，细胞成像表明发光材料DPA-BN-BFT和DMA-DPA-BN-BFT可以高度选择性和灵敏地检测活 MCF-7 细胞中的脂滴 (LD)。总体而言，这项工作为合理设计和合成具有 AIE 特征的先进 BN-多环芳烃提供了新的视角，并引发了氮杂硼烷化学新功能和新性质的发现。
更新日期：2022-02-11
中文翻译：
聚集引起猝灭到聚集诱导发射转变：基于BN掺杂的多环芳烃对亚细胞细胞器特异性成像的精确调整
具有硼-氮（BN）部分的多环芳烃（PAHs）由于其有趣的电子和光电特性而引起了极大的兴趣。然而，迄今为止报道的大多数 BN 融合 π 系统难以修改并表现出传统的聚集引起的猝灭 (ACQ) 特性。这种现象极大地限制了它们的应用范围。因此，继续努力寻找新颖的、结构独特的和功能多样的结构是非常可取的。在这里，我们提出了一种一石二鸟的策略，包括通过灵活的区域选择性功能化工程同时探索反应性以及调整含 BN π 骨架的光学和电子特性。这样，三种新型功能化 BN 发光体（DPA-BN-BFT, MeO-DPA-BN-BFT和DMA-DPA-BN-BFT ) 具有相似的结构。有趣的是，DPA-BN-BFT、MeO-DPA-BN-BFT和DMA-DPA-BN-BFT表现出完全不同的发射行为。荧光剂 DPA-BN-BFT和MeO-DPA-BN-BFT表现出典型的 ACQ 效应；形成鲜明对比的是，DMA-DPA-BN-BFT具有显着的聚集诱导发射（AIE）效应。据我们所知，这是第一份将 ACQ 和 AIE 特性整合到一个具有细微修饰结构的 BN 芳族骨架中的报告。对晶体结构和理论计算的综合分析表明，较大的扭转角、多种分子间相互作用和紧密的晶体堆积模式赋予了DMA-DPA-BN-BFT较强的AIE行为。更重要的是，细胞成像表明发光材料DPA-BN-BFT和DMA-DPA-BN-BFT可以高度选择性和灵敏地检测活 MCF-7 细胞中的脂滴 (LD)。总体而言，这项工作为合理设计和合成具有 AIE 特征的先进 BN-多环芳烃提供了新的视角，并引发了氮杂硼烷化学新功能和新性质的发现。
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