Phosphate-phosphate oligomerization drives higher order co-assemblies with stacks of cyanostar macrocycles

Chemical Science
Elisabeth M FatilaAmar H Flood

Abstract

The importance of phosphate in biology and chemistry has long motivated investigation of its recognition. Despite this interest, phosphate's facile oligomerization is only now being examined following the discovery of complexes of anion-anion dimers of hydroxyanions. Here we address how oligomerization dictates phosphate's recognition properties when engaged with planar cyanostar macrocycles that can also oligomerize by stacking. The crystal structure of cyanostar with phosphate shows an unprecedented tetrameric stack of cyanostar macrocycles threaded by a phosphate trimer, [H2PO4···H2PO4···H2PO4]3-. The solution behaviour, studied as a function of solvent quality, highlights how dimers and trimers of phosphate drive formation of higher order stacks of cyanostar into dimer, trimer and tetramer co-assemblies. Solution behaviors differ significantly from simpler complexes of bisulfate hydroxyanion dimers. Phosphate oligomerization is: (1) preferred over ion pairing with tetrabutylammonium cations, (2) inhibits disassembly of the complexes upon dilution, and (3) resists interference from competitive anion solvation. The phosphate oligomers also appear critical for stability; complexation of just one phosphate with cyanostars is un...Continue Reading

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Citations

Feb 26, 2019·Physical Chemistry Chemical Physics : PCCP·Íñigo IribarrenDavid Quiñonero
Jan 19, 2019·Chemistry : a European Journal·Dajana BarišićVladislav Tomišić
May 7, 2020·Physical Chemistry Chemical Physics : PCCP·Luis Miguel AzofraIbon Alkorta
Apr 22, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·David QuiñoneroJose Elguero
Oct 10, 2018·Chemical Communications : Chem Comm·Lisa M EytelDarren W Johnson
Jun 12, 2018·Journal of the American Chemical Society·Edward G SheetzAmar H Flood
Nov 19, 2019·Inorganic Chemistry·Sheng-Yin HuangValerie C Pierre
Aug 24, 2018·Organic Letters·Chenxing GuoJonathan L Sessler
Aug 14, 2020·The Journal of Organic Chemistry·Samuel I EtkindTimothy M Swager
Nov 23, 2018·Journal of the American Chemical Society·Fred C ParksAmar H Flood
Apr 27, 2019·Journal of the American Chemical Society·Jennifer F NealHeather C Allen
Jul 11, 2020·ACS Applied Materials & Interfaces·Huang WuJ Fraser Stoddart
Feb 25, 2020·The Journal of Physical Chemistry. a·Luis Miguel AzofraIbon Alkorta
Jun 17, 2020·Journal of the American Chemical Society·Ayan DharaAmar H Flood
Dec 7, 2018·Chemical Reviews·Teresa L MakoMindy Levine
Nov 13, 2020·Journal of the American Chemical Society·Thomas S C MacDonaldJonathon E Beves
Aug 20, 2021·Chemistry : a European Journal·Jana M HolthoffStefan M Huber

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Methods Mentioned

BETA
NMR

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