Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter September 29, 2018

Synthesis of “three-legged” tri-dentate podand ligands incorporating long-chain aliphatic moieties, for water remediators, and for isolating metal ions in non-aqueous solution

Justin Pothoof, Michal Ruprecht, Ben D. Sliwinski, Ben M. Sosnowski, Polly R. Fitzgerald, Steven Kosmas and Mark A. Benvenuto
From the journal Physical Sciences Reviews

Abstract

Two molecules, each including tris-2-amino-ethyleneamine (tren), have been produced using a Schiff’s base condensation and long-chain, aliphatic aldehydes. The syntheses are straightforward and can be run in air at ambient temperature. The ability of these molecules to complex with metal ions makes them good candidates for water remediation. The ability of these ligands to hold metal ions in 0.03M non-aqueous solutions was unexpected. Their syntheses and characterization are discussed.

References

[1] Pfeiffer, P, Breith E, Lübbe E, Tsumaki T. Tricyclische orthokondensierte Nebenvalenzringe. Liebigs Ann Chem. 1933;503:84–130.10.1002/jlac.19335030106Search in Google Scholar

[2] Saline Water Conversion Vol. 27. Washington, DC: American Chemical Society, 1960 January 01Search in Google Scholar

[3] In: Gould RF, editor(s). Saline water conversion - II Vol. 38. Washington, DC: American Chemical Society, 1963 January 01Search in Google Scholar

[4] In: Kavanaugh MC, Leckie JO, editor(s). Particulates in water: characterization, fate, effects, and removal, advances in chemistry Vol. 189. Washington, DC: American Chemical Society, 1980 November10.1021/ba-1980-0189Search in Google Scholar

[5] Vickers A. The handbook of water use and conservation. Amherst, MA: WaterFlow Press, 20011-931579-07Search in Google Scholar

[6] National Academies Press. Urban stormwater management in the United States. Washington, DC: National Academies Press, 2009Search in Google Scholar

[7] Binnie, C. Basic water treatment. 4th ed. London: Royal Society of Chemistry, 2009. ISBN 9781847558787.10.1680/bwt.36086Search in Google Scholar

[8] National Academies Press. Letter report assessing the usgs national water quality assessment program’s science framework. Washington, DC: National Academies Press, 2010Search in Google Scholar

[9] National Academies Press. Letter report assessing the usgs national water quality assessment program’s science plan. Washington, DC: National Academies Press, 2011Search in Google Scholar

[10] Ghaffour, N, Missimer TM, Amy GL. Technical review and evaluation of the economics of water desalination: current and future challenges for better water supply sustainability. Desalination. 2013;309:197–207.10.1016/j.desal.2012.10.015Search in Google Scholar

[11] In: Baker A, editor(s). Environmental chemistry of lakes and reservoirs Vol. 237. Washington, DC: American Chemical Society, 19941994. 05 May 1994Search in Google Scholar

[12] Water: Our Thirsty World. National Geographic, A Special Issue. National Geographic, 2010.Search in Google Scholar

[13] Benvenuto, MA. Industrial chemistry. Berlin: DeGruyter, 2014.10.1515/9783110295900Search in Google Scholar

[14] Paolieri M. Ferdinand Münz: EDTA and 40 years of inventions. Bull Hist Chem. 2017;42:133–40Search in Google Scholar

[15] Izatt, RM. The synthesis and ion bindings of synthetic multidentate macrocyclic compounds. Chem Rev. 1974;74:351–84.10.1021/cr60289a003Search in Google Scholar PubMed

[16] Bradshaw, JS, Izatt RM. Crown ethers: the search for selective ion ligating agents. Acc Chem Res. 1997;30:338–45.10.1021/ar950211mSearch in Google Scholar

[17] Gordon, AE, Xu J, Raymond KN, Durbin P. Rational design of sequestering agents for Plutonium and other actinides. Chem Rev. 2003;103:4207–82.10.1021/cr990114xSearch in Google Scholar PubMed

[18] Sessler, JL, Melfi PJ, Dan Pantos G. Uranium complexes of multidentate N-donor ligands. Coord Chem Rev. 2006;250:816–43.10.1016/j.ccr.2005.10.007Search in Google Scholar

[19] Hayes, CE, Leznoff DB. Actinide coordination and organometallic complexes with multidentate polyamido ligands. Coord Chem Rev. 2014;266–267:155–70.10.1016/j.ccr.2013.11.020Search in Google Scholar

[20] Jin, Y, Wang Q, Taynton P, Zhang W. Dynamic covalent chemistry approaches toward macrocycles, molecular cages, and polymers. Acc Chem Res. 2014;47:1575–86.10.1021/ar500037vSearch in Google Scholar PubMed

[21] He, Q, Zhang Z, BrewsterJT, Lynch VM, Kim SK, Sessler JL. Hemispherand-strapped calix[4]pyrrole: an ion-pair receptor for the recognition and extraction of Lithium Nitrite. J Am Chem Soc. 2016;138:9779–82.10.1021/jacs.6b05713Search in Google Scholar PubMed

[22] Kosmas S. Growing your green chemistry mind set. Green Chem Process. 2017;2:137–43.Walter DeGruyter, GmbH.10.1515/9783110445923-008Search in Google Scholar

[23] Sessler, J, Davis JM. Sapphyrins: versatile anion binding agents. Acc Chem Res. 2001;34:989–97.10.1021/ar980117gSearch in Google Scholar PubMed

[24] Liu, Z, Samanta A, Lei J, Sun J, Wanng Y, Stoddart JF. Cation-dependent gold recovery with α-Cyclodextrin facilitated by second-sphere coordination. J Am Chem Soc. 2016;138:11643–53.10.1021/jacs.6b04986Search in Google Scholar PubMed

[25] Lee, S, Hua Y, Flood AH. β-sheet-like Hydrogen bonds interlock the helical turns of a photoswitchable foldamer to enhance the binding and release of Chloride. J Org Chem. 2014;79:8383–96.10.1021/jo501595kSearch in Google Scholar PubMed

[26] Bonnesen PV, Delmau LH, Moyer BA, Lumetta GJ. Development of effective solvent modifiers for the solvent extraction of Cesium from Alkaline high‐level tank waste. Solv Extra Ion Exc. 2003;21:141–7010.1081/SEI-120018944Search in Google Scholar

[27] Lohrman, J, Telikepalli H, Johnson TS, Jackson TA, Day VW, Bowman-James K. Pyrazinetetracarboxamide: a duplex ligand for Palladium(II). Inorg Chem. 2016;55:5098–100.10.1021/acs.inorgchem.6b00594Search in Google Scholar PubMed

Published Online: 2018-09-29

© 2018 Walter de Gruyter GmbH, Berlin/Boston

Scroll Up Arrow