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

doi:10.1039/C9QO01377F

This content will become publicly available on January 2, 2021

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:: 2020-01-01

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 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.

Copy to clipboard


                    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.

Copy to clipboard


                    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.

Copy to clipboard


                    
@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       = ,

  volume       = ,

  place        = {United Kingdom},

  year         = {2020},

  month        = {1}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

This content will become publicly available on January 2, 2021

Publisher's Version of Record

DOI: 10.1039/C9QO01377F

Other availability

Search WorldCat to find libraries that may hold this journal

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

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

Martínez-Máñez, Ramón; Sancenón, Félix
Chemical Reviews, Vol. 103, Issue 11
DOI: 10.1021/cr010421e

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

Kim, Sung Kuk; Sessler, Jonathan L.
Accounts of Chemical Research, Vol. 47, Issue 8
DOI: 10.1021/ar500157a

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

Heinze, C.; Meyer, S.; Goris, N.
Earth System Dynamics, Vol. 6, Issue 1
DOI: 10.5194/esd-6-327-2015

Intracellular pH.
journal, April 1981

Roos, A.; Boron, W. F.
Physiological Reviews, Vol. 61, Issue 2
DOI: 10.1152/physrev.1981.61.2.296

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

De Cian, Anne; DeLemos, Elsa; Mergny, Jean-Louis
Journal of the American Chemical Society, Vol. 129, Issue 7
DOI: 10.1021/ja067352b

Anion receptor chemistry: highlights from 2010
journal, January 2012

Wenzel, Marco; Hiscock, Jennifer R.; Gale, Philip A.
Chem. Soc. Rev., Vol. 41, Issue 1
DOI: 10.1039/C1CS15257B

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

Gale, Philip A.; Caltagirone, Claudia
Chemical Society Reviews, Vol. 44, Issue 13
DOI: 10.1039/C4CS00179F

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

Gale, Philip A.
Chemical Society Reviews, Vol. 39, Issue 10
DOI: 10.1039/c001871f

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

Liu, Yun; Sengupta, Arkajyoti; Raghavachari, Krishnan
Chem, Vol. 3, Issue 3
DOI: 10.1016/j.chempr.2017.08.003

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

Krieg, Brian J.; Taghavi, Seyed Mohammad; Amidon, Gordon L.
Journal of Pharmaceutical Sciences, Vol. 103, Issue 11
DOI: 10.1002/jps.24108

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

Casey, Joseph R.
Biochemistry and Cell Biology, Vol. 84, Issue 6
DOI: 10.1139/o06-184

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

Gale, Philip A.; Sessler, Jonathan L.; Král, Vladimír
Journal of the American Chemical Society, Vol. 118, Issue 21
DOI: 10.1021/ja960307r

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

Saha, Indrajit; Lee, Jeong Tae; Lee, Chang-Hee
European Journal of Organic Chemistry, Vol. 2015, Issue 18
DOI: 10.1002/ejoc.201403701

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

Gale, Philip A.; Busschaert, Nathalie; Haynes, Cally J. E.
Chem. Soc. Rev., Vol. 43, Issue 1
DOI: 10.1039/C3CS60316D

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

Davis, Jeffery T.; Gale, Philip A.; Okunola, Oluyomi A.
Nature Chemistry, Vol. 1, Issue 2
DOI: 10.1038/nchem.178

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

Sessler, Jonathan L.; Gross, Dustin E.; Cho, Won-Seob
Journal of the American Chemical Society, Vol. 128, Issue 37
DOI: 10.1021/ja064012h

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

Lee, Chang-Hee; Miyaji, Hidekazu; Yoon, Dae-Wi
Chem. Commun., Issue 1
DOI: 10.1039/B713183F

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

Lee, Chang-Hee; Lee, Jin-Suk; Na, Hee-Kyung
The Journal of Organic Chemistry, Vol. 70, Issue 6
DOI: 10.1021/jo0487146

Anion receptor chemistry: highlights from 2007
journal, January 2009

Caltagirone, Claudia; Gale, Philip A.
Chem. Soc. Rev., Vol. 38, Issue 2
DOI: 10.1039/B806422A

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

Mulugeta, Endale; He, Qing; Sareen, Divya
Chem, Vol. 3, Issue 6
DOI: 10.1016/j.chempr.2017.10.007

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

Ko, Sung-Kyun; Kim, Sung Kuk; Share, Andrew
Nature Chemistry, Vol. 6, Issue 10
DOI: 10.1038/nchem.2021

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

Zeng, Ning
Advances in Atmospheric Sciences, Vol. 20, Issue 5
DOI: 10.1007/BF02915395

Calixpyrroles
journal, January 1998

Gale, Philip A.; Sessler, Jonathan L.; Král, Vladimír
Chemical Communications, Issue 1
DOI: 10.1039/a706280j

Amide-Based Ligands for Anion Coordination
journal, December 2006

Kang, Sung Ok; Begum, Rowshan Ara; Bowman-James, Kristin
Angewandte Chemie International Edition, Vol. 45, Issue 47
DOI: 10.1002/anie.200602006

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

Beer, Paul D.; Gale, Philip A.
Angewandte Chemie International Edition, Vol. 40, Issue 3
DOI: 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO;2-P

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

Oh, Ju Hyun; Kim, Jeong Hyeon; Kim, Dong Sub
Organic Letters, Vol. 21, Issue 11
DOI: 10.1021/acs.orglett.9b01515

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

Kim, Sung Kuk; Lynch, Vincent M.; Sessler, Jonathan L.
Organic Letters, Vol. 16, Issue 23
DOI: 10.1021/ol502991t

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

Suzuki, Iwao; Ui, Mihoko; Yamauchi, Akiyo
Journal of the American Chemical Society, Vol. 128, Issue 14
DOI: 10.1021/ja055772f

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

He, Qing; Williams, Neil J.; Oh, Ju Hyun
Angewandte Chemie International Edition, Vol. 57, Issue 37
DOI: 10.1002/anie.201805127

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

Vaughan-Jones, Richard D.; Spitzer, Kenneth W.
Biochemistry and Cell Biology, Vol. 80, Issue 5
DOI: 10.1139/o02-157

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

Zippin, Jonathan H.; Levin, Lonny R.; Buck, Jochen
Trends in Endocrinology & Metabolism, Vol. 12, Issue 8
DOI: 10.1016/S1043-2760(01)00454-4

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

Sigman, Daniel M.; Boyle, Edward A.
Nature, Vol. 407, Issue 6806
DOI: 10.1038/35038000

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

Chen, Y.
Science, Vol. 289, Issue 5479
DOI: 10.1126/science.289.5479.625

Similar records in OSTI.GOV collections:

Pyrrole- and Naphthobipyrrole-Strapped Calix[4]pyrroles as Azide Anion Receptors

Journal Article Kim, Seung Hyeon ; Lee, Juhoon ; Vargas-Zúñiga, Gabriela I. ; ... - Journal of Organic Chemistry

The binding interactions between the azide anion (N3–) and the strapped calix[4]pyrroles 2 and 3 bearing auxiliary hydrogen bonding donors on the bridging moieties, as well as of normal calix[4]pyrrole 1, were investigated via 1H NMR spectroscopic and isothermal titration calorimetry analyses. The resulting data revealed that receptors 2 and 3 have significantly higher affinities for the azide anion in organic media as compared with the unfunctionalized calix[4]pyrrole 1 and other azide receptors reported to date. Single crystal X-ray diffraction analyses and calculations using density functional theory revealed that receptor 2 binds CsN3 in two distinct structural forms. As judgedmore »« less
DOI: 10.1021/acs.joc.7b03135
Uranyl dication mediated photoswitching of a calix[4]pyrrole-based metal coordination cage

Journal Article Lee, Juhoon ; Brewster, James T. ; Song, Bo ; ... - Chemical Communications

A set of self-assembled tri- and tetrapodal metal coordination cage structures ( cage-1 and cage-2 , respectively) constructed from the uranyl dication (UO ₂ ²⁺ ) and a dibenzoic acid functionalised cis -calix[4]pyrrole ( 1 ) are described.
Cited by 1
DOI: 10.1039/C8CC05160G
The Supramolecular Chemistry of Selective Anion Recognition for Anions of Environmental Relevance

Technical Report Sessler, Jonathan L.

Work at carried out at ORNL since the inception of the project has served to demonstrate that the calix[4]pyrroles from the co-P.I.'s laboratory at the Univ. of Texas strongly enhance the extraction of sulfate by tricaprylmethylammonium nitrate or chloride in the presence of excess nitrate and chloride. Similar results were found in the case of the tetraamide macrocycles synthesized in the Bowman-James laboratory (Univ. of Kansas). Effort at the Univ. of Texas thus focused on generating new pyrrole-amide macrocycles that might combine the most favorable aspects of the calixpyrroles and the tetraamides. This culminated in the synthesis of several newmore »« less
DOI: 10.2172/884859

Full Text Available
Structure determination of two structural analogs, named 3-[1-(2-fluoro-4-biphenyl)ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C23H16F2N4S) and 3-[1-(2-fluoro-4-biphenyl)ethyl]-6-(4-chlorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C23H16ClFN4S) by synchrotron X-ray powder diffraction

Journal Article Gündoğdu, Gülsüm ; Aytaç, Sevim Peri ; Müller, Melanie ; ... - Powder Diffraction

Two novel compounds, 3-[1-(2-fluoro-4-biphenyl)ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C ₂₃H ₁₆F ₂N ₄S) (1) and 3-[1-(2-fluoro-4-biphenyl)ethyl]-6-(4-chlorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C ₂₃H ₁₆ClFN ₄S) (2), have been designed and synthesized as cytotoxic agents. The compounds were characterized by infrared, proton nuclear magnetic resonance, mass spectral data, elemental analysis and X-ray powder diffraction. The present study comprises spectral data and crystal structures of these novel compounds determined from synchrotron X-ray powder diffraction data. The structure solutions were obtained by simulated annealing. The final structures were achieved by Rietveld refinement using soft restraints for all bond lengths, bond angles, and planar groups. Both compounds crystallize in space groupmore »« less
DOI: 10.1017/S0885715617001105
Next Generation Extractants for Cesium Separation from High-Level Waste: From Fundamental Concepts to Site Implementation

Technical Report Bartsch, Richard A.

Solvent extraction with a lipophilic calix[4]arenebiscrown-6 ligand is currently the selected technology for removal of radioactive cesium-137 from DOE nuclear wastes. In this collaborative DOE-EMSP project, related "second-generation" extractants are being synthesized at Texas Tech University (TTU) and their alkali metal cation compexation and separation abilities evaluated at TTU and Oak Ridge National Laboratory (ORNL). The novel feature of the "second-generation" calix[4]arenecrown extractants is incorporation of a proton-ionizable group into the ligand structure. This modification markedly enhances the efficiency with which metal ions can be extracted from an aqueous phase into an organic diluent, since concomitant extraction of a hydrophilicmore »« less
DOI: 10.2172/885050

Full Text Available

Similar Records

This content will become publicly available on January 2, 2021

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

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

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

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

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