Fluorescent pH sensor constructed from a heteroatom-containing luminogen with tunable AIE and ICT characteristics

Fluorescent pH sensor constructed from a heteroatom-containing luminogen with tunable AIE and ICT characteristics
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DOI:
10.1039/c3sc50648g
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发表时间:
2013-07
期刊:
影响因子:
8.4
通讯作者:
Zhiyong Yang;Wei Qin;J. Lam;Sijie Chen;H. Sung;Ian D. Williams;B. Tang
Zhiyong Yang;Wei Qin;J. Lam;Sijie Chen;H. Sung;Ian D. Williams;B. Tang
中科院分区:
化学1区
文献类型:
--
作者:
Zhiyong Yang;Wei Qin;J. Lam;Sijie Chen;H. Sung;Ian D. Williams;B. Tang

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设计并合成了一种含杂原子的有机荧光剂1-(4-吡啶基)-1-苯基-2-(9-咔唑基)乙烯(CP 3E)。CP 3E的咔唑和吡啶单元之间存在给体-受体相互作用,引起分子内电荷转移(ICT)效应。而它在溶液中发射微弱,它成为一个强大的发射体在聚集状态,证明了聚集诱导发射(AIE)的现象。它的发射可以通过重复的质子化和去质子化在蓝态和暗态之间可逆地切换。这种行为使其能够在溶液和固体状态下作为荧光pH传感器工作,并作为检测酸性和碱性有机蒸气的化学传感器。NMR光谱,单晶X-射线衍射和计算分析表明,在质子化和去质子化后的CP 3E的吡啶基单元和分子构象的电子亲合性的变化是负责这样的传感过程。
A heteroatom-containing organic fluorophore 1-(4-pyridinyl)-1-phenyl-2-(9-carbazolyl)ethene (CP3E) was designed and synthesized. CP3E exhibits the effect of intramolecular charge transfer (ICT) caused by the donor–acceptor interaction between its carbazole and pyridine units. Whereas it emits faintly in solution, it becomes a strong emitter in the aggregated state, demonstrating the phenomenon of aggregation-induced emission (AIE). Its emission can be reversibly switched between blue and dark states by repeated protonation and deprotonation. Such behaviour enables it to work as a fluorescent pH sensor in both solution and the solid state and as a chemosensor for detecting acidic and basic organic vapors. Analyses by NMR spectroscopy, single-crystal X-ray diffraction and computational calculations suggest that the change in electron affinity of the pyridinyl unit and molecular conformation of CP3E upon protonation and deprotonation is responsible for such sensing processes.