A new halogen bonding 1,2-iodo-triazolium-triazole benzene motif for anion recognition

Thanthapatra Bunchuay; Andrew Docker; Nicholas G. White; Paul D. Beer

doi:10.1016/j.poly.2021.115482

A new halogen bonding 1,2-iodo-triazolium-triazole benzene motif for anion recognition

Thanthapatra Bunchuay, Andrew Docker, Nicholas G. White, Paul D. Beer^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

The synthesis of a series of halogen bonding (XB) acyclic anion receptors based on a novel 1,2-iodo-triazolium-triazole benzene motif is reported. A combination of one- and two-dimensional ¹H and ¹⁹F NMR spectroscopic techniques elucidate key conformational effects associated with the incorporation of ortho-substituted iodo-triazole based XB donors. ¹H NMR anion titration experiments highlight the anion recognition potency of a mono-cationic XB iodo-triazolium-triazole benzene receptor, remarkably forming stronger halide complexes in comparison to a dicationic hydrogen bonding (HB) bis-proto-triazolium receptor analogue. X-ray crystal structure analysis provide insights into halide binding induced conformational changes and coordination modes, revealing the unique electronic and steric consequences associated with multidentate XB donor arrays.

Original language	English
Article number	115482
Journal	Polyhedron
Volume	209
DOIs	https://doi.org/10.1016/j.poly.2021.115482
Publication status	Published - 15 Nov 2021

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title = "A new halogen bonding 1,2-iodo-triazolium-triazole benzene motif for anion recognition",

abstract = "The synthesis of a series of halogen bonding (XB) acyclic anion receptors based on a novel 1,2-iodo-triazolium-triazole benzene motif is reported. A combination of one- and two-dimensional 1H and 19F NMR spectroscopic techniques elucidate key conformational effects associated with the incorporation of ortho-substituted iodo-triazole based XB donors. 1H NMR anion titration experiments highlight the anion recognition potency of a mono-cationic XB iodo-triazolium-triazole benzene receptor, remarkably forming stronger halide complexes in comparison to a dicationic hydrogen bonding (HB) bis-proto-triazolium receptor analogue. X-ray crystal structure analysis provide insights into halide binding induced conformational changes and coordination modes, revealing the unique electronic and steric consequences associated with multidentate XB donor arrays.",

keywords = "Anion Recognition, Halogen Bonding, Host-Guest Chemistry, Sigma-Hole Interactions, Supramolecular",

author = "Thanthapatra Bunchuay and Andrew Docker and White, \{Nicholas G.\} and Beer, \{Paul D.\}",

note = "Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

year = "2021",

month = nov,

day = "15",

doi = "10.1016/j.poly.2021.115482",

language = "English",

volume = "209",

journal = "Polyhedron",

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T1 - A new halogen bonding 1,2-iodo-triazolium-triazole benzene motif for anion recognition

AU - Bunchuay, Thanthapatra

AU - Docker, Andrew

AU - White, Nicholas G.

AU - Beer, Paul D.

PY - 2021/11/15

Y1 - 2021/11/15

N2 - The synthesis of a series of halogen bonding (XB) acyclic anion receptors based on a novel 1,2-iodo-triazolium-triazole benzene motif is reported. A combination of one- and two-dimensional 1H and 19F NMR spectroscopic techniques elucidate key conformational effects associated with the incorporation of ortho-substituted iodo-triazole based XB donors. 1H NMR anion titration experiments highlight the anion recognition potency of a mono-cationic XB iodo-triazolium-triazole benzene receptor, remarkably forming stronger halide complexes in comparison to a dicationic hydrogen bonding (HB) bis-proto-triazolium receptor analogue. X-ray crystal structure analysis provide insights into halide binding induced conformational changes and coordination modes, revealing the unique electronic and steric consequences associated with multidentate XB donor arrays.

AB - The synthesis of a series of halogen bonding (XB) acyclic anion receptors based on a novel 1,2-iodo-triazolium-triazole benzene motif is reported. A combination of one- and two-dimensional 1H and 19F NMR spectroscopic techniques elucidate key conformational effects associated with the incorporation of ortho-substituted iodo-triazole based XB donors. 1H NMR anion titration experiments highlight the anion recognition potency of a mono-cationic XB iodo-triazolium-triazole benzene receptor, remarkably forming stronger halide complexes in comparison to a dicationic hydrogen bonding (HB) bis-proto-triazolium receptor analogue. X-ray crystal structure analysis provide insights into halide binding induced conformational changes and coordination modes, revealing the unique electronic and steric consequences associated with multidentate XB donor arrays.

KW - Anion Recognition

KW - Halogen Bonding

KW - Host-Guest Chemistry

KW - Sigma-Hole Interactions

KW - Supramolecular

UR - https://www.scopus.com/pages/publications/85115382272

U2 - 10.1016/j.poly.2021.115482

DO - 10.1016/j.poly.2021.115482

M3 - Article

SN - 0277-5387

VL - 209

JO - Polyhedron

JF - Polyhedron

M1 - 115482

ER -

A new halogen bonding 1,2-iodo-triazolium-triazole benzene motif for anion recognition

Abstract

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