Tripodal Organic Cages with Unconventional CH···O Interactions for Perchlorate Remediation in Water

Jayanta Samanta; Miao Tang; Mingshi Zhang; Russell P Hughes; Richard J Staples; Chenfeng Ke

doi:10.1021/jacs.3c06379

Tripodal Organic Cages with Unconventional CH···O Interactions for Perchlorate Remediation in Water

J Am Chem Soc. 2023 Oct 11;145(40):21723-21728. doi: 10.1021/jacs.3c06379. Epub 2023 Sep 28.

Authors

Jayanta Samanta^{1

2}, Miao Tang¹, Mingshi Zhang¹, Russell P Hughes¹, Richard J Staples³, Chenfeng Ke¹

Affiliations

¹ Department of Chemistry, Dartmouth College, 41 College Street, Hanover, New Hampshire 03755, United States.
² Department of Chemistry, College of Engineering and Technology, SRM Institute of Science and Technology, Kattankulathur 603203, India.
³ Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824, United States.

PMID: 37769032
DOI: 10.1021/jacs.3c06379

Abstract

Perchlorate anions used in industry are harmful pollutants in groundwater. Therefore, selectively binding perchlorate provides solutions for environmental remediation. Here, we synthesized a series of tripodal organic cages with highly preorganized C_sp3-H bonds that exhibit selectively binding to perchlorate in organic solvents and water. These cages demonstrated binding affinities to perchlorate of 10⁵-10⁶ M^-1 at room temperature, along with high selectivity over competing anions, such as iodide and nitrate. Through single crystal structure analysis and density functional theory calculations, we identified unconventional C_sp3-H···O interactions as the primary driving force for perchlorate binding. Additionally, we successfully incorporated this cage into a 3D-printable polymer network, showcasing its efficacy in removing perchlorate from water.