TY - JOUR
T1 - New Heteropolycyclic Structures for Fluoride Anion Sensing by Naked-Eye Visualization
AU - Zhu, Lei
AU - Wen, Ying
AU - Liu, Haoran
AU - Zeng, Zebing
AU - Zhao, Jingzhe
AU - Jiang, Jianhui
AU - Miao, Shaobin
N1 - Funding Information:
The authors would like to acknowledge the financial support by the National Natural Science Foundation of China (NSFC-21271070) and the Department of Chemistry and Physics at Augusta University.
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/2/28
Y1 - 2018/2/28
N2 - Fluoride anion (F−) plays an important and fundamental role in chemical, biological, pathological, and environmental processes. It is highly desired to develop new methods for facial and efficient F− detection. Herein we present the synthesis and characterization of two effective fluoride ion probes and their selective F− sensing by naked-eye visualization. A N-heteroannelated anthraquinone derivative, compound I, was prepared by a cyclocondensation reaction of 1,2-diaminoanthraquinone with 1,6-bis(triisopropylsilyl)-hexa-l,5-diyne-3,4-dione. Compound I was treated with malononitrile in the presence of Lehnert reagent to afford an HCl adduct, compound II, and an aza-polycyclic aromatic compound III. All three compounds were characterized crystallographically and were studied photochemically. Similarly, 2,3-diamino-1,4-anthraquinone reacted with 1,6-bis(triisopropylsilyl)-hexa-l,5-diyne-3,4-dione to afford compound IV, which reacted with malononitrile in the presence of Lehnert reagent to yield compound V. Compounds III and V are sensitive and selective probes for the detection of F− with significant color changes. The detection by naked eye visualization is rapid and facile, showing both compounds are potential probes for fluoride ion sensing.
AB - Fluoride anion (F−) plays an important and fundamental role in chemical, biological, pathological, and environmental processes. It is highly desired to develop new methods for facial and efficient F− detection. Herein we present the synthesis and characterization of two effective fluoride ion probes and their selective F− sensing by naked-eye visualization. A N-heteroannelated anthraquinone derivative, compound I, was prepared by a cyclocondensation reaction of 1,2-diaminoanthraquinone with 1,6-bis(triisopropylsilyl)-hexa-l,5-diyne-3,4-dione. Compound I was treated with malononitrile in the presence of Lehnert reagent to afford an HCl adduct, compound II, and an aza-polycyclic aromatic compound III. All three compounds were characterized crystallographically and were studied photochemically. Similarly, 2,3-diamino-1,4-anthraquinone reacted with 1,6-bis(triisopropylsilyl)-hexa-l,5-diyne-3,4-dione to afford compound IV, which reacted with malononitrile in the presence of Lehnert reagent to yield compound V. Compounds III and V are sensitive and selective probes for the detection of F− with significant color changes. The detection by naked eye visualization is rapid and facile, showing both compounds are potential probes for fluoride ion sensing.
KW - Anthraquinone derivative
KW - Fluoride anion probe
KW - Fused-ring systems
KW - Heterocycles
KW - Naked-eye sensing
KW - X-ray diffraction
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U2 - 10.1002/slct.201702864
DO - 10.1002/slct.201702864
M3 - Article
AN - SCOPUS:85042643331
SN - 2365-6549
VL - 3
SP - 2336
EP - 2342
JO - ChemistrySelect
JF - ChemistrySelect
IS - 8
ER -