Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity

doi:10.1039/C9QO01377F

Title: Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity

Abstract

Calix[4]pyrroles 1 and 2 , diametrically strapped with a phenanthroline via ester and amide linkages, respectively, have been synthesized as anion receptors.

Authors:

Heo, Nam Jung ^[1]; Oh, Ju Hyun ^[1]; Lee, Jeong Tae ^[2];

^[3];

^[4];

^[1]

Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University, Jinju 52828, Korea
Department of Chemistry and Institute of Applied Chemistry, Hallym University, Chuncheon 24252, Korea
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
Department of Chemistry, The University of Texas at Austin, Austin, USA

Publication Date:: 2020-02-05

Sponsoring Org.:: USDOE

OSTI Identifier:: 1581835

Grant/Contract Number:: FG02-01ER15186

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Organic Chemistry Frontiers (Online)

Additional Journal Information:: Journal Name: Organic Chemistry Frontiers (Online) Journal Volume: 7 Journal Issue: 3; Journal ID: ISSN 2052-4129

Publisher:: Royal Society of Chemistry (RSC)

Country of Publication:: United Kingdom

Language:: English

Citation Formats


                    Heo, Nam Jung, Oh, Ju Hyun, Lee, Jeong Tae, He, Qing, Sessler, Jonathan L., and Kim, Sung Kuk. Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity.  United Kingdom: N. p., 2020. 
        Web.  doi:10.1039/C9QO01377F.

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                    Heo, Nam Jung, Oh, Ju Hyun, Lee, Jeong Tae, He, Qing, Sessler, Jonathan L., & Kim, Sung Kuk. Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity.  United Kingdom.  doi:10.1039/C9QO01377F.

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                    Heo, Nam Jung, Oh, Ju Hyun, Lee, Jeong Tae, He, Qing, Sessler, Jonathan L., and Kim, Sung Kuk. Wed .  
        "Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity".  United Kingdom.  doi:10.1039/C9QO01377F.

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@article{osti_1581835,

  title        = {Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity},

  author       = {Heo, Nam Jung and Oh, Ju Hyun and Lee, Jeong Tae and He, Qing and Sessler, Jonathan L. and Kim, Sung Kuk},

  abstractNote = {Calix[4]pyrroles 1 and 2 , diametrically strapped with a phenanthroline via ester and amide linkages, respectively, have been synthesized as anion receptors.},

  doi          = {10.1039/C9QO01377F},

  journal      = {Organic Chemistry Frontiers (Online)},

  number       = 3,

  volume       = 7,

  place        = {United Kingdom},

  year         = {2020},

  month        = {2}

}

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DOI: 10.1039/C9QO01377F

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Title: Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity

Abstract

Citation Formats

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

Calix[4]pyrrole-Based Ion Pair Receptors journal, June 2014

The ocean carbon sink – impacts, vulnerabilities and challenges journal, January 2015

Intracellular pH. journal, April 1981

Highly Efficient G-Quadruplex Recognition by Bisquinolinium Compounds journal, February 2007

Anion receptor chemistry: highlights from 2010 journal, January 2012

Anion sensing by small molecules and molecular ensembles journal, January 2015

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

Anion Binding in Solution: Beyond the Electrostatic Regime journal, September 2017

In Viv o Predictive Dissolution: Transport Analysis of the CO 2 , Bicarbonate In Vivo Buffer System journal, November 2014

Why bicarbonate?This paper is one of a selection of papers published in this Special Issue, entitled CSBMCB — Membrane Proteins in Health and Disease. journal, December 2006

Calix[4]pyrroles: Old Yet New Anion-Binding Agents journal, January 1996

Recent Advancements in Calix[4]pyrrole-Based Anion-Receptor Chemistry: Calix[4]pyrrole-Based Anion Receptor Chemistry journal, March 2015

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

Using small molecules to facilitate exchange of bicarbonate and chloride anions across liposomal membranes journal, April 2009

Calix[4]pyrrole as a Chloride Anion Receptor: Solvent and Countercation Effects journal, September 2006

Strapped and other topographically nonplanar calixpyrrole analogues. Improved anion receptors journal, January 2008

Cis- and Trans-Strapped Calix[4]pyrroles Bearing Phthalamide Linkers: Synthesis and Anion-Binding Properties journal, March 2005

Thermodynamics of solvation of ions. Part 5.—Gibbs free energy of hydration at 298.15 K journal, January 1991

Anion receptor chemistry: highlights from 2007 journal, January 2009

Recognition, Sensing, and Trapping of Bicarbonate Anions with a Dicationic meso-Bis(benzimidazolium) Calix[4]pyrrole journal, December 2017

Synthetic ion transporters can induce apoptosis by facilitating chloride anion transport into cells journal, August 2014

Glacial-interglacial atmospheric CO2 change —The glacial burial hypothesis journal, September 2003

Calixpyrroles journal, January 1998

Amide-Based Ligands for Anion Coordination journal, December 2006

Cryptand-like anion receptors journal, January 2010

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

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

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

Supramolecular Probe for Bicarbonate Exhibiting Anomalous Pyrene Fluorescence in Aqueous Media journal, April 2006

Selective Solid-Liquid and Liquid-Liquid Extraction of Lithium Chloride Using Strapped Calix[4]pyrroles journal, June 2018

Role of bicarbonate in the regulation of intracellular pH in the mammalian ventricular myocyte journal, October 2002

CO2/HCO3−-responsive soluble adenylyl cyclase as a putative metabolic sensor journal, October 2001

Glacial/interglacial variations in atmospheric carbon dioxide journal, October 2000

Soluble Adenylyl Cyclase as an Evolutionarily Conserved Bicarbonate Sensor journal, July 2000

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

Calix[4]pyrrole-Based Ion Pair Receptors
journal, June 2014

The ocean carbon sink – impacts, vulnerabilities and challenges
journal, January 2015

Intracellular pH.
journal, April 1981

Highly Efficient G-Quadruplex Recognition by Bisquinolinium Compounds
journal, February 2007

Anion receptor chemistry: highlights from 2010
journal, January 2012

Anion sensing by small molecules and molecular ensembles
journal, January 2015

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

Anion Binding in Solution: Beyond the Electrostatic Regime
journal, September 2017

In Viv o Predictive Dissolution: Transport Analysis of the CO 2 , Bicarbonate In Vivo Buffer System
journal, November 2014

Why bicarbonate?This paper is one of a selection of papers published in this Special Issue, entitled CSBMCB — Membrane Proteins in Health and Disease.
journal, December 2006

Calix[4]pyrroles: Old Yet New Anion-Binding Agents
journal, January 1996

Recent Advancements in Calix[4]pyrrole-Based Anion-Receptor Chemistry: Calix[4]pyrrole-Based Anion Receptor Chemistry
journal, March 2015

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

Using small molecules to facilitate exchange of bicarbonate and chloride anions across liposomal membranes
journal, April 2009

Calix[4]pyrrole as a Chloride Anion Receptor: Solvent and Countercation Effects
journal, September 2006

Strapped and other topographically nonplanar calixpyrrole analogues. Improved anion receptors
journal, January 2008

Cis- and Trans-Strapped Calix[4]pyrroles Bearing Phthalamide Linkers: Synthesis and Anion-Binding Properties
journal, March 2005

Thermodynamics of solvation of ions. Part 5.—Gibbs free energy of hydration at 298.15 K
journal, January 1991

Anion receptor chemistry: highlights from 2007
journal, January 2009

Recognition, Sensing, and Trapping of Bicarbonate Anions with a Dicationic meso-Bis(benzimidazolium) Calix[4]pyrrole
journal, December 2017

Synthetic ion transporters can induce apoptosis by facilitating chloride anion transport into cells
journal, August 2014

Glacial-interglacial atmospheric CO2 change —The glacial burial hypothesis
journal, September 2003

Calixpyrroles
journal, January 1998

Amide-Based Ligands for Anion Coordination
journal, December 2006

Cryptand-like anion receptors
journal, January 2010

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

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

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

Supramolecular Probe for Bicarbonate Exhibiting Anomalous Pyrene Fluorescence in Aqueous Media
journal, April 2006

Selective Solid-Liquid and Liquid-Liquid Extraction of Lithium Chloride Using Strapped Calix[4]pyrroles
journal, June 2018

Role of bicarbonate in the regulation of intracellular pH in the mammalian ventricular myocyte
journal, October 2002

CO2/HCO3−-responsive soluble adenylyl cyclase as a putative metabolic sensor
journal, October 2001

Glacial/interglacial variations in atmospheric carbon dioxide
journal, October 2000

Soluble Adenylyl Cyclase as an Evolutionarily Conserved Bicarbonate Sensor
journal, July 2000