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A conjugated BODIPY–triphenylamine multi-aldoxime: Sonogashira coupling, ratiometric chemodosimeter and rapid detection of hypochlorite with two-photon excited fluorescence†
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2018-03-17 00:00:00 , DOI: 10.1039/c8nj00368h Chao Xu 1, 2, 3, 4 , Ying Qian 1, 2, 3, 4 , Zheng-qing Qi 2, 3, 4, 5 , Chang-gui Lu 2, 3, 4, 5 , Yi-ping Cui 2, 3, 4, 5
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2018-03-17 00:00:00 , DOI: 10.1039/c8nj00368h Chao Xu 1, 2, 3, 4 , Ying Qian 1, 2, 3, 4 , Zheng-qing Qi 2, 3, 4, 5 , Chang-gui Lu 2, 3, 4, 5 , Yi-ping Cui 2, 3, 4, 5
Affiliation
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A conjugated BODIPY–triphenylamine multi-aldoxime (BTN) was designed and synthesized by the Sonogashira coupling reaction. The chemodosimeter showed a red emission (670 nm), fast response (within seconds), high selectivity and good sensitivity towards hypochlorite based on the redox reaction of four aldoximes. BTN possessed two original absorption peaks at 366 nm and 588 nm, respectively, corresponding to fluorescence emissions at 440 nm and 660 nm, which exhibited a ratiometric change in the presence of hypochlorite. With the addition of hypochlorite, the redox reaction of aldoxime led to the termination of isomerization of the C![[double bond, length as m-dash]](https://www.rsc.org/images/entities/char_e001.gif)
N bond, the fluorescence intensity at 660 nm gradually changed from weak to strong, accompanied by a slight 10 nm red-shift; in contrast, the fluorescence intensity began to decrease at 440 nm. Moreover, as the two-photon excited fluorescent NaOCl probe, BTN afforded an enhanced signal response for hypochlorite at 686 nm under two-photon excitation (λTPEFex = 800 nm). Meanwhile, successful imaging of living cells was carried out for BTN towards hypochlorite in A-549 cells. The results demonstrated that BTN had potential application prospects and was promising for practical application in biological systems and environmental systems.
中文翻译：
结合的BODIPY-三苯胺多醛肟：Sonogashira偶联，化学计量比和通过双光子激发荧光快速检测次氯酸盐†
通过Sonogashira偶联反应设计并合成了一种共轭的BODIPY-三苯胺多醛肟（BTN）。基于四种醛肟的氧化还原反应，化学光度计显示红色发射（670 nm），快速响应（数秒内），高选择性和对次氯酸盐的良好敏感性。BTN分别在366 nm和588 nm处具有两个原始吸收峰，分别对应于440 nm和660 nm处的荧光发射，在次氯酸盐存在下显示出比例变化。随着次氯酸盐的添加，醛肟的氧化还原反应导致C的异构化终止。通过N键，660 nm处的荧光强度逐渐从弱变为强，伴随着轻微的10 nm红移; 相反，荧光强度在440nm处开始降低。此外，由于双光子激发荧光的NaOCl探针，BTN，得到次氯酸盐在686纳米下双光子激发（增强的信号响应λ TPEF EX = 800纳米）。同时，成功地对A-549细胞中的次氯酸盐对BTN的活细胞进行了成像。结果表明，BTN具有潜在的应用前景，并有望在生物系统和环境系统中的实际应用。
更新日期：2018-03-17
N bond, the fluorescence intensity at 660 nm gradually changed from weak to strong, accompanied by a slight 10 nm red-shift; in contrast, the fluorescence intensity began to decrease at 440 nm. Moreover, as the two-photon excited fluorescent NaOCl probe, BTN afforded an enhanced signal response for hypochlorite at 686 nm under two-photon excitation (λTPEFex = 800 nm). Meanwhile, successful imaging of living cells was carried out for BTN towards hypochlorite in A-549 cells. The results demonstrated that BTN had potential application prospects and was promising for practical application in biological systems and environmental systems.
中文翻译：
结合的BODIPY-三苯胺多醛肟：Sonogashira偶联，化学计量比和通过双光子激发荧光快速检测次氯酸盐†
通过Sonogashira偶联反应设计并合成了一种共轭的BODIPY-三苯胺多醛肟（BTN）。基于四种醛肟的氧化还原反应，化学光度计显示红色发射（670 nm），快速响应（数秒内），高选择性和对次氯酸盐的良好敏感性。BTN分别在366 nm和588 nm处具有两个原始吸收峰，分别对应于440 nm和660 nm处的荧光发射，在次氯酸盐存在下显示出比例变化。随着次氯酸盐的添加，醛肟的氧化还原反应导致C的异构化终止。
通过N键，660 nm处的荧光强度逐渐从弱变为强，伴随着轻微的10 nm红移; 相反，荧光强度在440nm处开始降低。此外，由于双光子激发荧光的NaOCl探针，BTN，得到次氯酸盐在686纳米下双光子激发（增强的信号响应λ TPEF EX = 800纳米）。同时，成功地对A-549细胞中的次氯酸盐对BTN的活细胞进行了成像。结果表明，BTN具有潜在的应用前景，并有望在生物系统和环境系统中的实际应用。
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