Sensing Techniques for Organochlorides through Intermolecular Interaction with Bicyclic Amidines

Park, Jong-Won; Jang, Lee-Woon; Jensen, Erik C.; Stockton, Amanda; Kim, Jungkyu

doi:10.3390/bios11110413

Title: Sensing Techniques for Organochlorides through Intermolecular Interaction with Bicyclic Amidines

Abstract

Toxic organochloride molecules are widely used in industry for various purposes. With their high volatility, the direct detection of organochlorides in environmental samples is challenging. Here, a new organochloride detection mechanism using 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) is introduced to simplify a sensing method with higher detection sensitivity. Three types of organochloride compounds-trichloroethylene (TCE), dichloromethane (DCM), and dichlorodiphenyltrichloroethane (DDT)—were targeted to understand DCM conjugation chemistry by using nuclear magnetic resonance (NMR) and liquid chromatography with a mass spectrometer (LC-MS). 13C-NMR spectra and LC-MS data indicated that DBN can be labeled on these organochloride compounds by chlorine–nitrogen interaction. Furthermore, to demonstrate the organochloride sensing capability, the labeling yield and limit of detection were determined by a colorimetric assay as well as micellar electrokinetic chromatography (MEKC). The interaction with DBN was most appreciable for TCE, among other organochlorides. TCE was detected at picomolar levels, which is two orders of magnitude lower than the maximum contaminant level set by the United States Environmental Protection Agency. MEKC, in conjunction with this DBN-labeling method, enables us to develop a field-deployable sensing platform for detecting toxic organochlorides with high sensitivity.

Authors:

; Jang, Lee-Woon; Jensen, Erik C.; Stockton, Amanda;

Publication Date:: 2021-10-23

Sponsoring Org.:: USDOE

OSTI Identifier:: 1827216

Grant/Contract Number:: SC0009553-1

Resource Type:: Published Article

Journal Name:: Biosensors

Additional Journal Information:: Journal Name: Biosensors Journal Volume: 11 Journal Issue: 11; Journal ID: ISSN 2079-6374

Publisher:: MDPI AG

Country of Publication:: Switzerland

Language:: English

Citation Formats


                    Park, Jong-Won, Jang, Lee-Woon, Jensen, Erik C., Stockton, Amanda, and Kim, Jungkyu. Sensing Techniques for Organochlorides through Intermolecular Interaction with Bicyclic Amidines.  Switzerland: N. p., 2021. 
Web.  doi:10.3390/bios11110413.

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                    Park, Jong-Won, Jang, Lee-Woon, Jensen, Erik C., Stockton, Amanda, & Kim, Jungkyu. Sensing Techniques for Organochlorides through Intermolecular Interaction with Bicyclic Amidines.  Switzerland.  https://doi.org/10.3390/bios11110413

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                    Park, Jong-Won, Jang, Lee-Woon, Jensen, Erik C., Stockton, Amanda, and Kim, Jungkyu. Sat .  
"Sensing Techniques for Organochlorides through Intermolecular Interaction with Bicyclic Amidines".  Switzerland.  https://doi.org/10.3390/bios11110413.

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@article{osti_1827216,

  title        = {Sensing Techniques for Organochlorides through Intermolecular Interaction with Bicyclic Amidines},

  author       = {Park, Jong-Won and Jang, Lee-Woon and Jensen, Erik C. and Stockton, Amanda and Kim, Jungkyu},

  abstractNote = {Toxic organochloride molecules are widely used in industry for various purposes. With their high volatility, the direct detection of organochlorides in environmental samples is challenging. Here, a new organochloride detection mechanism using 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) is introduced to simplify a sensing method with higher detection sensitivity. Three types of organochloride compounds-trichloroethylene (TCE), dichloromethane (DCM), and dichlorodiphenyltrichloroethane (DDT)—were targeted to understand DCM conjugation chemistry by using nuclear magnetic resonance (NMR) and liquid chromatography with a mass spectrometer (LC-MS). 13C-NMR spectra and LC-MS data indicated that DBN can be labeled on these organochloride compounds by chlorine–nitrogen interaction. Furthermore, to demonstrate the organochloride sensing capability, the labeling yield and limit of detection were determined by a colorimetric assay as well as micellar electrokinetic chromatography (MEKC). The interaction with DBN was most appreciable for TCE, among other organochlorides. TCE was detected at picomolar levels, which is two orders of magnitude lower than the maximum contaminant level set by the United States Environmental Protection Agency. MEKC, in conjunction with this DBN-labeling method, enables us to develop a field-deployable sensing platform for detecting toxic organochlorides with high sensitivity.},

  doi          = {10.3390/bios11110413},

  journal      = {Biosensors},

  number       = 11,

  volume       = 11,

  place        = {Switzerland},

  year         = {2021},

  month        = {10}

}

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Title: Sensing Techniques for Organochlorides through Intermolecular Interaction with Bicyclic Amidines

Abstract

Citation Formats

Evanescent Fiber-Optic Chemical Sensor for Monitoring Volatile Organic Compounds in Water journal, July 1997

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Facile fabrication of polyaniline coated titania nanotube arrays as fiber coatings for solid phase microextraction coupled to high performance liquid chromatography for sensitive determination of UV filters in environmental water samples journal, January 2017

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Qualitative By-Product Identification of Plasma-Assisted TCE Abatement by Mass Spectrometry and Fourier-Transform Infrared Spectroscopy journal, August 2011

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Organochlorine pesticides (OCPs) in South Asian region: A review journal, April 2014

Biogenic Nanopalladium Based Remediation of Chlorinated Hydrocarbons in Marine Environments journal, December 2013

Effects of pyrolysis temperature on soybean stover- and peanut shell-derived biochar properties and TCE adsorption in water journal, August 2012

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journal, February 2015

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journal, July 2014

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journal, May 2013

Potential role of organochlorine pesticides in the pathogenesis of neurodevelopmental, neurodegenerative, and neurobehavioral disorders: A review
journal, January 2016

Developmental Exposure to Environmental Toxicants
journal, October 2015

Synthesis and electro-optical properties of new conjugated hybrid polymers based on furan and fluorene units
journal, February 2013

Recent developments in the detailed characterization of polymers by multidimensional chromatography
journal, June 2012

Biosensor Technology for Pesticides—A review
journal, January 2015

A Field Trial of TCE Phytoremediation by Genetically Modified Poplars Expressing Cytochrome P450 2E1
journal, May 2017

Artificial Neural Networks for the Automated Detection of Trichloroethylene by Passive Fourier Transform Infrared Spectrometry
journal, March 2000

Nitrogen-chlorine donor-acceptor interactions dominate the structure of crystalline cyanuric chloride
journal, August 1992

Two amidine derivatives studied by 1H, 13C, 14N, 15N NMR and GIAO-CHF calculations
journal, January 1999

Qualitative By-Product Identification of Plasma-Assisted TCE Abatement by Mass Spectrometry and Fourier-Transform Infrared Spectroscopy
journal, August 2011

Trichloroethylene sensing in water based on SERS with multifunctional Au/TiO ₂ core–shell nanocomposites
journal, January 2015

Experimental and Theoretical Thermodynamic Study of Distillable Ionic Liquid 1,5-Diazabicyclo[4.3.0]non-5-enium Acetate
journal, September 2016

Soft ionization mass spectroscopy: Insights into the polymerization mechanism
journal, January 2013

Development of a Screening Approach to Interpret Human Biomonitoring Data on Volatile Organic Compounds: Reverse Dosimetry on Biomonitoring Data for Trichloroethylene: Development of a Screening Approach to Interpret Human Biomonitoring Data
journal, October 2007

Macroporous Carbon Supported Zerovalent Iron for Remediation of Trichloroethylene
journal, December 2016

Phytoremediation of Organic Contaminants in Soil and Groundwater
journal, September 2008

Predicting Cellulose Solvating Capabilities of Acid-Base Conjugate Ionic Liquids
journal, September 2013

Effects of environmental organochlorine pesticides on human breast cancer: Putative involvement on invasive cell ability: Organochlorine Effects on Human Breast Cancer
journal, August 2013

A review on environmental monitoring of water organic pollutants identified by EU guidelines
journal, February 2018

Formation of organochlorine by-products in bleached laundry
journal, February 2013

On the origin of some controversial ions ( m/z 59, 60, 77, and 119) in the thermospray reagent plasma from ammonium acetate
journal, March 1994

Organochlorine pesticides (OCPs) in South Asian region: A review
journal, April 2014

Biogenic Nanopalladium Based Remediation of Chlorinated Hydrocarbons in Marine Environments
journal, December 2013

Effects of pyrolysis temperature on soybean stover- and peanut shell-derived biochar properties and TCE adsorption in water
journal, August 2012

Concentration of Trichloroethylene in Breast Milk and Household Water from Nogales, Arizona
journal, August 2012

Sustainability of cellulose dissolution and regeneration in 1,5-diazabicyclo[4.3.0]non-5-enium acetate: a batch simulation of the IONCELL-F process
journal, January 2015

Environmental Remediation of Chlorinated Hydrocarbons Using Biopolymer Stabilized Iron Loaded Halloysite Nanotubes
journal, October 2017

Halogen bonding interaction of chloromethane with several nitrogen donating molecules: addressing the nature of the chlorine surface σ-hole
journal, January 2014

LC-MS/MS analysis of permethylated N-glycans facilitating isomeric characterization
journal, October 2016

Gas chromatography/atmospheric pressure chemical ionization/mass spectrometry for the analysis of organochlorine pesticides and polychlorinated biphenyls in human serum
journal, July 2016

Electromagnetic Induction of Zerovalent Iron (ZVI) Powder and Nanoscale Zerovalent Iron (NZVI) Particles Enhances Dechlorination of Trichloroethylene in Contaminated Groundwater and Soil: Proof of Concept
journal, December 2015

A fully automated microfluidic micellar electrokinetic chromatography analyzer for organic compound detection
journal, January 2016

Microfabricated Gas Chromatograph for the Selective Determination of Trichloroethylene Vapor at Sub-Parts-Per-Billion Concentrations in Complex Mixtures
journal, August 2011

TCE Dechlorination Rates, Pathways, and Efficiency of Nanoscale Iron Particles with Different Properties
journal, March 2005

Capillary Electrophoresis
journal, December 2015

Investigating the Underappreciated Hydrolytic Instability of 1,8-Diazabicyclo[5.4.0]undec-7-ene and Related Unsaturated Nitrogenous Bases
journal, July 2019

A robust and modular synthesis of ynamides
journal, January 2015