Efficient synthesis of pillar[5]quinone for rapid identification of aromatic nitro explosives
- 1Academy of Interdisciplinary Studies on Intelligent Molecules, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University Tianjin 300387 P. R. China
- 2College of Aerospace Science and Engineering, National University of Defense Technology Changsha 410073 P. R. China
Abstract
An efficient synthesis of pillar[5]quinone (Q5) is reported for the rapid identification of aromatic nitro explosives. A record-high synthetic yield of 96% on a gram scale for Q5 can be achieved via a two-step reaction process involving the demethylation of pillar[5]arene to hydroxypillar[5]arene, followed by oxidation with Oxone to form Q5. In addition, by modifying amino silicon spheres with Q5 to prepare a stationary phase material (Q5-Sil) for high-performance liquid chromatography (HPLC), efficient separation of eight typical aromatic nitro-explosives was achieved using a single column. The underlying mechanism of the separation of aromatic nitro-explosives in the Q5-Sil-packed column resulted from dipole–dipole interactions, hydrophobic effects, and steric factors between Q5 and analytes. This work achieved the quantitative synthesis of Q5, established a novel method of macrocyclic modification of chromatographic column stationary phase materials, and provided a mixed mechanism for the HPLC-based separation of aromatic nitro-explosives, expanding the interdisciplinary applications of macrocyclic supramolecular chemistry in the field of analytical separation science.
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BibTeX
@article{zhang2026efficient,
title = {{Efficient synthesis of pillar[5]quinone for rapid identification of aromatic nitro explosives}},
author = {Yue-Yi Zhang and Lu Wang and Jiabin Wu and Si-Tong Fan and Xin-Yu Che and Yu-Han Wang and Zhi-Yuan Zhang and Yao-Hua Liu and Xing Zhou and Yue Liu and Chunju Li},
journal = {RSC advances},
year = {2026},
month = oct,
doi = {10.1039/d6ra06389f},
url = {https://europepmc.org/article/PMC/PMC13656025},
note = {CC BY},
}
RIS
TY - JOUR
TI - Efficient synthesis of pillar[5]quinone for rapid identification of aromatic nitro explosives
AU - Yue-Yi Zhang
AU - Lu Wang
AU - Jiabin Wu
AU - Si-Tong Fan
AU - Xin-Yu Che
AU - Yu-Han Wang
AU - Zhi-Yuan Zhang
AU - Yao-Hua Liu
AU - Xing Zhou
AU - Yue Liu
AU - Chunju Li
PY - 2026
DA - 2026/10/12
JO - RSC advances
DO - 10.1039/d6ra06389f
UR - https://europepmc.org/article/PMC/PMC13656025
AB - An efficient synthesis of pillar[5]quinone (Q5) is reported for the rapid identification of aromatic nitro explosives. A record-high synthetic yield of 96% on a gram scale for Q5 can be achieved via a two-step reaction process involving the demethylation of pillar[5]arene to hydroxypillar[5]arene, followed by oxidation with Oxone to form Q5. In addition, by modifying amino silicon spheres with Q5 to prepare a stationary phase material (Q5-Sil) for high-performance liquid chromatography (HPLC), efficient separation of eight typical aromatic nitro-explosives was achieved using a single column. The underlying mechanism of the separation of aromatic nitro-explosives in the Q5-Sil-packed column resulted from dipole–dipole interactions, hydrophobic effects, and steric factors between Q5 and analytes. This work achieved the quantitative synthesis of Q5, established a novel method of macrocyclic modification of chromatographic column stationary phase materials, and provided a mixed mechanism for the HPLC-based separation of aromatic nitro-explosives, expanding the interdisciplinary applications of macrocyclic supramolecular chemistry in the field of analytical separation science.
SN - 2046-2069
ER -