Small triiminopyrrolic molecular cage with high affinity and selectivity for fluoride

Han, Hye Jin; Oh, Ju Hyun; Sessler, Jonathan L.; Kim, Sung Kuk

doi:10.1039/C9CC05613K

Title: Small triiminopyrrolic molecular cage with high affinity and selectivity for fluoride

Abstract

We report that a small molecular cage (4) with high affinity and complete selectivity for fluoride to the limit of detection over other competing small anions was synthesized. Cage 4 was also found to retain the encapsulated fluoride anion within its cavity even after one or two pyrrolic NH protons were subject to deprotonation.

Authors:

Han, Hye Jin ^[1]; Oh, Ju Hyun ^[1];

^[2]; Kim, Sung Kuk ^[1]

Gyeongsang National Univ., Jinju (Korea)
Univ. of Texas, Austin, TX (United States)

Publication Date:: 2019-08-12

Research Org.:: Univ. of Texas, Austin, TX (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Research Foundation of Korea (NRF); Robert A. Welch Foundation

OSTI Identifier:: 1598888

Alternate Identifier(s):: OSTI ID: 1558130

Grant/Contract Number:: FG02-01ER15186; NRF-2019R1F1A1061780; 2017R1A4A1014595; F-0018

Resource Type:: Accepted Manuscript

Journal Name:: ChemComm

Additional Journal Information:: Journal Volume: 55; Journal Issue: 73; Journal ID: ISSN 1359-7345

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Han, Hye Jin, Oh, Ju Hyun, Sessler, Jonathan L., and Kim, Sung Kuk. Small triiminopyrrolic molecular cage with high affinity and selectivity for fluoride.  United States: N. p., 2019. 
Web.  doi:10.1039/C9CC05613K.

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                    Han, Hye Jin, Oh, Ju Hyun, Sessler, Jonathan L., & Kim, Sung Kuk. Small triiminopyrrolic molecular cage with high affinity and selectivity for fluoride.  United States.  https://doi.org/10.1039/C9CC05613K

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                    Han, Hye Jin, Oh, Ju Hyun, Sessler, Jonathan L., and Kim, Sung Kuk. Mon .  
"Small triiminopyrrolic molecular cage with high affinity and selectivity for fluoride".  United States.  https://doi.org/10.1039/C9CC05613K.  https://www.osti.gov/servlets/purl/1598888.

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@article{osti_1598888,

  title        = {Small triiminopyrrolic molecular cage with high affinity and selectivity for fluoride},

  author       = {Han, Hye Jin and Oh, Ju Hyun and Sessler, Jonathan L. and Kim, Sung Kuk},

  abstractNote = {We report that a small molecular cage (4) with high affinity and complete selectivity for fluoride to the limit of detection over other competing small anions was synthesized. Cage 4 was also found to retain the encapsulated fluoride anion within its cavity even after one or two pyrrolic NH protons were subject to deprotonation.},

  doi          = {10.1039/C9CC05613K},

  journal      = {ChemComm},

  number       = 73,

  volume       = 55,

  place        = {United States},

  year         = {2019},

  month        = {8}

}

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Journal Article:

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Accepted Manuscript (DOE)

Publisher's Version of Record

https://doi.org/10.1039/C9CC05613K

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Cited by: 6 works

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Figures / Tables:

Figure 1: Partial ¹H NMR spectra recorded during the titration of cage 4 (3 mM) with TBAF (tetrabutylammonium fluoride) in the presence of TBACl, TBABr, TBAI, and (TBA)₂SO₄ (>10 equiv. each) in CDCl₃.

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Figures / Tables found in this record:

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Title: Small triiminopyrrolic molecular cage with high affinity and selectivity for fluoride

Abstract

Citation Formats

Figures / Tables:

A Half-century of Community Water Fluoridation in the United States: Review and Commentary journal, March 1993

Systematic review of water fluoridation journal, October 2000

Expertise, Health, and Popular Opinion: Debating Water Fluoridation, 1945–80 journal, September 2008

The role of Fluoride in the Prevention of Osteoporosis journal, June 1998

Determination of urinary fluoride by ion chromatography journal, March 1993

Developmental neurotoxicity of industrial chemicals journal, December 2006

Relationship between cardiopulmonary mortality and cancer risk and quantitative exposure to polycyclic aromatic hydrocarbons, fluorides, and dust in two prebake aluminum smelters journal, March 2009

Fluoride Effects: The Two Faces of Janus journal, August 2010

Molecular mechanisms of fluoride toxicity journal, November 2010

Serum Fluoride and Sialic Acid Levels in Osteosarcoma journal, April 2009

Fluorescence and Colorimetric Chemosensors for Fluoride-Ion Detection journal, March 2014

Fluoride Ion Complexation and Sensing Using Organoboron Compounds journal, July 2010

Highlights on contemporary recognition and sensing of fluoride anion in solution and in the solid state journal, January 2013

Recognition and sensing of fluoride anion journal, January 2009

Selective recognition of fluoride anion in water by a copper( ii ) center embedded in a hydrophobic cavity journal, January 2014

Cone Calix[4]arene Diethyl Ester Strapped Calix[4]pyrrole: A Selective Receptor for the Fluoride Anion journal, November 2014

Calix[4]pyrroles with Shortest Possible Strap: Exclusively Selective toward Fluoride Ion journal, August 2015

Anion Recognition and Sensing: The State of the Art and Future Perspectives journal, January 2001

Fluorogenic and Chromogenic Chemosensors and Reagents for Anions journal, November 2003

Anion receptor chemistry: highlights from 2011 and 2012 journal, January 2014

Anion receptor chemistry: highlights from 2010 journal, January 2012

Anion receptor chemistry: highlights from 2008 and 2009 journal, January 2010

Amide-Based Ligands for Anion Coordination journal, December 2006

Cryptand-like anion receptors journal, January 2010

Tricyclic Host for Linear Anions journal, September 2010

Fluoride-Facilitated Deuterium Exchange from DMSO- d 6 to Polyamide-Based Cryptands journal, October 2004

Anion Binding Motifs: Topicity and Charge in Amidocryptands journal, October 2005

Trapped Bifluoride journal, March 2006

Reversible Reduction of Oxygen to Peroxide Facilitated by Molecular Recognition journal, January 2012

Convenient synthesis of tripodal-pyrrole receptor and anion binding properties journal, November 2009

Oxoanion recognition by benzene-based tripodal pyrrolic receptors journal, January 2012

Synthesis and Anion Recognition Features of a Molecular Cage Containing Both Hydrogen Bond Donors and Acceptors journal, May 2019

Pyrrolic tripodal receptors for carbohydrates. Role of functional groups and binding geometry on carbohydrate recognition journal, January 2011

Air-Stable N , N ′-Dihydroporphycene: A Quinoxaline-Fused Tetrapyrrolic Macrocycle That Detects Fluoride Anion via Deprotonation journal, February 2019

Trapped Bifluoride journal, March 2006

Fluorogenic and Chromogenic Chemosensors and Reagents for Anions journal, February 2004

Developmental neurotoxicity of industrial chemicals journal, March 2007

Amide-Based Ligands for Anion Coordination journal, March 2007

Fighting Deactivation: Classical and Emerging Strategies for Efficient Stabilization of Molecular Electrocatalysts journal, January 2020

Anthracene‐Based Amido−Amine Cage Receptor for Anion Recognition under Neutral Aqueous Conditions journal, December 2019

A Half-century of Community Water Fluoridation in the United States: Review and Commentary
journal, March 1993

Systematic review of water fluoridation
journal, October 2000

Expertise, Health, and Popular Opinion: Debating Water Fluoridation, 1945–80
journal, September 2008

The role of Fluoride in the Prevention of Osteoporosis
journal, June 1998

Determination of urinary fluoride by ion chromatography
journal, March 1993

Developmental neurotoxicity of industrial chemicals
journal, December 2006

Relationship between cardiopulmonary mortality and cancer risk and quantitative exposure to polycyclic aromatic hydrocarbons, fluorides, and dust in two prebake aluminum smelters
journal, March 2009

Fluoride Effects: The Two Faces of Janus
journal, August 2010

Molecular mechanisms of fluoride toxicity
journal, November 2010

Serum Fluoride and Sialic Acid Levels in Osteosarcoma
journal, April 2009

Fluorescence and Colorimetric Chemosensors for Fluoride-Ion Detection
journal, March 2014

Fluoride Ion Complexation and Sensing Using Organoboron Compounds
journal, July 2010

Highlights on contemporary recognition and sensing of fluoride anion in solution and in the solid state
journal, January 2013

Recognition and sensing of fluoride anion
journal, January 2009

Selective recognition of fluoride anion in water by a copper( ii ) center embedded in a hydrophobic cavity
journal, January 2014

Cone Calix[4]arene Diethyl Ester Strapped Calix[4]pyrrole: A Selective Receptor for the Fluoride Anion
journal, November 2014

Calix[4]pyrroles with Shortest Possible Strap: Exclusively Selective toward Fluoride Ion
journal, August 2015

Anion Recognition and Sensing: The State of the Art and Future Perspectives
journal, January 2001

Fluorogenic and Chromogenic Chemosensors and Reagents for Anions
journal, November 2003

Anion receptor chemistry: highlights from 2011 and 2012
journal, January 2014

Anion receptor chemistry: highlights from 2010
journal, January 2012

Anion receptor chemistry: highlights from 2008 and 2009
journal, January 2010

Amide-Based Ligands for Anion Coordination
journal, December 2006

Cryptand-like anion receptors
journal, January 2010

Tricyclic Host for Linear Anions
journal, September 2010

Fluoride-Facilitated Deuterium Exchange from DMSO- d ₆ to Polyamide-Based Cryptands
journal, October 2004

Anion Binding Motifs: Topicity and Charge in Amidocryptands
journal, October 2005

Trapped Bifluoride
journal, March 2006

Reversible Reduction of Oxygen to Peroxide Facilitated by Molecular Recognition
journal, January 2012

Convenient synthesis of tripodal-pyrrole receptor and anion binding properties
journal, November 2009

Oxoanion recognition by benzene-based tripodal pyrrolic receptors
journal, January 2012

Synthesis and Anion Recognition Features of a Molecular Cage Containing Both Hydrogen Bond Donors and Acceptors
journal, May 2019

Pyrrolic tripodal receptors for carbohydrates. Role of functional groups and binding geometry on carbohydrate recognition
journal, January 2011

Air-Stable N , N ′-Dihydroporphycene: A Quinoxaline-Fused Tetrapyrrolic Macrocycle That Detects Fluoride Anion via Deprotonation
journal, February 2019

Trapped Bifluoride
journal, March 2006

Fluorogenic and Chromogenic Chemosensors and Reagents for Anions
journal, February 2004

Developmental neurotoxicity of industrial chemicals
journal, March 2007

Amide-Based Ligands for Anion Coordination
journal, March 2007

Fighting Deactivation: Classical and Emerging Strategies for Efficient Stabilization of Molecular Electrocatalysts
journal, January 2020

Anthracene‐Based Amido−Amine Cage Receptor for Anion Recognition under Neutral Aqueous Conditions
journal, December 2019