Metallocalix[4]arene Polymers for Gravimetric Detection of N-Nitrosodialkylamines
- Ru-Qiang LuRu-Qiang LuDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United StatesMore by Ru-Qiang Lu
- ,
- Weize YuanWeize YuanDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United StatesMore by Weize Yuan
- ,
- Robert G. CroyRobert G. CroyDepartment of Biological Engineering and Center for Environmental Health Sciences, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United StatesMore by Robert G. Croy
- ,
- John M. EssigmannJohn M. EssigmannDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United StatesDepartment of Biological Engineering and Center for Environmental Health Sciences, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United StatesMore by John M. Essigmann
- , and
- Timothy M. Swager*Timothy M. Swager*[email protected]Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United StatesDepartment of Biological Engineering and Center for Environmental Health Sciences, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United StatesMore by Timothy M. Swager
Abstract
N-Nitrosamines are found in food, drugs, air, water, and soil. They pose a significant risk to human health because of their carcinogenicity; consequently, materials that can be used to selectively and sensitively detect nitrosamines are needed. In this work, we designed and synthesized two polymers bearing calix[4]arene or 4-tert-butylcalix[4]arene tungsten–imido complexes (PCalixH and PCalixtBu) as N-nitrosodimethylamine (NDMA) receptors. The interaction between metallocalix[4]arene monomers/polymers and NDMA was confirmed by 1H NMR and IR spectroscopy. Single-crystal X-ray analysis further revealed that the host–guest interaction is based on binding of the terminal oxygen of NDMA to tungsten within the calixarene cavity. Gravimetric detection of NDMA was performed on a quartz crystal microbalance (QCM) in air. Both polymers show responses to NDMA, with PCalixtBu exhibiting a low theoretical limit of detection of 5 ppb for NDMA. The sensor also shows high selectivity toward NDMA and moderate humidity tolerance. This work provides a sensitive sensor for detection of NDMA and also offers a class of new, selective, and efficient NDMA receptors for the future design of NDMA sensors and NDMA extraction materials.
Cited By
This article is cited by 9 publications.
- Tianhao Jia, Nianyou Pan, Xiangmin Song, Yongchao Gao, Zhixiang Zhang, Hanhong Xu, Chen Zhao. Preparation and Characterization of Insecticide/Calix[4]arene Complexes and Their Enhanced Insecticidal Activities against Plutella xylostella. Journal of Agricultural and Food Chemistry 2023, 71 (14) , 5576-5584. https://doi.org/10.1021/acs.jafc.3c00657
- Marko Trampuž, Mateja Žnidarič, Fabrice Gallou, Zdenko Časar. Does the Red Shift in UV–Vis Spectra Really Provide a Sensing Option for Detection of N-Nitrosamines Using Metalloporphyrins?. ACS Omega 2023, 8 (1) , 1154-1167. https://doi.org/10.1021/acsomega.2c06615
- Ru-Qiang Lu, Weize Yuan, Haosheng Feng, Shao-Xiong Lennon Luo, You-Chi Mason Wu, Samuel I. Etkind, Mohanraja Kumar, Timothy M. Swager. Porous Polymers Containing Metallocalix[4]arene for the Extraction of Tobacco-Specific Nitrosamines. Chemistry of Materials 2022, 34 (23) , 10623-10630. https://doi.org/10.1021/acs.chemmater.2c02713
- Timothy M. Swager. Molecular Shape and Polar Order in Columnar Liquid Crystals. Accounts of Chemical Research 2022, 55 (20) , 3010-3019. https://doi.org/10.1021/acs.accounts.2c00452
- Benjamin Z. Zydlewski, Hsin-Che Lu, Hugo Celio, Delia J. Milliron. Site-Selective Ion Intercalation Controls Spectral Response in Electrochromic Hexagonal Tungsten Oxide Nanocrystals. The Journal of Physical Chemistry C 2022, 126 (34) , 14537-14546. https://doi.org/10.1021/acs.jpcc.2c02865
- Kai-Chi Chang, Chan-Yu Chen, Chin-Yun Hsu, Li-Wei Lee, Wen-Sheng Chung. A highly selective chromogenic and fluorogenic chemodosimeter for dual detection of Cu 2+ based on a redox-active calix[4]arene with isoxazolylchloroanthracene. The Analyst 2022, 147 (22) , 5105-5112. https://doi.org/10.1039/D2AN01201D
- Saúl Vallejos, Miriam Trigo-López, Ana Arnaiz, Álvaro Miguel, Asunción Muñoz, Aránzazu Mendía, José Miguel García. From Classical to Advanced Use of Polymers in Food and Beverage Applications. Polymers 2022, 14 (22) , 4954. https://doi.org/10.3390/polym14224954
- Samuel I. Etkind, Shun Ichii, Nathan A. Romero, Timothy M. Swager. Thiapillar[6]arene: Synthesis, Functionalization, and Properties. Synlett 2022, 33 (15) , 1532-1538. https://doi.org/10.1055/s-0040-1719932
- Xinyu Gao, Chuangyu Wei, Xiyou Li, Yanli Chen. Preparation of iron porphyrin/calix[8]arene/graphene ternary composites based on molecular recognition function and their dopamine electrochemical sensing properties. SCIENTIA SINICA Chimica 2022, 52 (8) , 1408-1416. https://doi.org/10.1360/SSC-2022-0038