Synthesis and Anion Recognition Features of a Molecular Cage Containing Both Hydrogen Bond Donors and Acceptors

Oh, Ju Hyun; Kim, Jeong Hyeon; Kim, Dong Sub; Han, Hye Jin; Lynch, Vincent M.; Sessler, Jonathan L.; Kim, Sung Kuk

doi:10.1021/acs.orglett.9b01515

Title: Synthesis and Anion Recognition Features of a Molecular Cage Containing Both Hydrogen Bond Donors and Acceptors

Abstract

A molecular cage, macrobicycle 2, containing amide and pyrrole groups as hydrogen-bonding donors and imine groups as hydrogen-bonding acceptors has been synthesized. Compound 2 was discovered to recognize tetrahedral oxyanions with high affinities, such as H₂PO₄^–, HSO₄^–, SO₄^2–, and HP₂O₇^3–, as well as the spherical halide anions, in chloroform. A single-crystal X-ray diffraction analysis illustrated that compound 2 formed a 1:1 complex with H₂PO₄^– in the solid state

Authors:

Oh, Ju Hyun ^[1]; Kim, Jeong Hyeon ^[1]; Kim, Dong Sub ^[2]; Han, Hye Jin ^[1]; Lynch, Vincent M. ^[2];

^[2];

^[1]

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

Publication Date:: Fri May 24 00:00:00 EDT 2019

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

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

OSTI Identifier:: 1615762

Grant/Contract Number:: FG02-01ER15186

Resource Type:: Accepted Manuscript

Journal Name:: Organic Letters

Additional Journal Information:: Journal Volume: 21; Journal Issue: 11; Journal ID: ISSN 1523-7060

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; amides; anions; nuclear magnetic resonance spectroscopy; receptors; titration

Citation Formats


                    Oh, Ju Hyun, Kim, Jeong Hyeon, Kim, Dong Sub, Han, Hye Jin, Lynch, Vincent M., Sessler, Jonathan L., and Kim, Sung Kuk. Synthesis and Anion Recognition Features of a Molecular Cage Containing Both Hydrogen Bond Donors and Acceptors.  United States: N. p., 2019. 
Web.  doi:10.1021/acs.orglett.9b01515.

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                    Oh, Ju Hyun, Kim, Jeong Hyeon, Kim, Dong Sub, Han, Hye Jin, Lynch, Vincent M., Sessler, Jonathan L., & Kim, Sung Kuk. Synthesis and Anion Recognition Features of a Molecular Cage Containing Both Hydrogen Bond Donors and Acceptors.  United States.  https://doi.org/10.1021/acs.orglett.9b01515

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                    Oh, Ju Hyun, Kim, Jeong Hyeon, Kim, Dong Sub, Han, Hye Jin, Lynch, Vincent M., Sessler, Jonathan L., and Kim, Sung Kuk. Fri .  
"Synthesis and Anion Recognition Features of a Molecular Cage Containing Both Hydrogen Bond Donors and Acceptors".  United States.  https://doi.org/10.1021/acs.orglett.9b01515.  https://www.osti.gov/servlets/purl/1615762.

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@article{osti_1615762,

  title        = {Synthesis and Anion Recognition Features of a Molecular Cage Containing Both Hydrogen Bond Donors and Acceptors},

  author       = {Oh, Ju Hyun and Kim, Jeong Hyeon and Kim, Dong Sub and Han, Hye Jin and Lynch, Vincent M. and Sessler, Jonathan L. and Kim, Sung Kuk},

  abstractNote = {A molecular cage, macrobicycle 2, containing amide and pyrrole groups as hydrogen-bonding donors and imine groups as hydrogen-bonding acceptors has been synthesized. Compound 2 was discovered to recognize tetrahedral oxyanions with high affinities, such as H2PO4–, HSO4–, SO42–, and HP2O73–, as well as the spherical halide anions, in chloroform. A single-crystal X-ray diffraction analysis illustrated that compound 2 formed a 1:1 complex with H2PO4– in the solid state},

  doi          = {10.1021/acs.orglett.9b01515},

  journal      = {Organic Letters},

  number       = 11,

  volume       = 21,

  place        = {United States},

  year         = {Fri May 24 00:00:00 EDT 2019},

  month        = {Fri May 24 00:00:00 EDT 2019}

}

Copy to clipboard

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https://doi.org/10.1021/acs.orglett.9b01515

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Works referencing / citing this record:

Molecularly Mixed Composite Membranes: Challenges and Opportunities
journal, March 2020

Zhu, Guanghui; O'Nolan, Daniel; Lively, Ryan P.
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Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity
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Title: Synthesis and Anion Recognition Features of a Molecular Cage Containing Both Hydrogen Bond Donors and Acceptors

Abstract

Citation Formats

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

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

Supramolecular Encapsulation of Tetrahedrally Hydrated Guests in a Tetrahedron Host journal, January 2012

Anion receptor chemistry: highlights from 2010 journal, January 2012

Highly Efficient Extraction of Sulfate Ions with a Tripodal Hexaurea Receptor journal, December 2010

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

Trapped Bifluoride journal, March 2006

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

Non-cyclic formylated dipyrromethanes as phosphate anion receptors journal, January 2016

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

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

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

Synthesis of 2,2′-bipyrrole-5-carboxaldehydes and their application in the synthesis of B-ring functionalized prodiginines and tambjamines journal, September 2013

C 3 v Symmetric Receptors Show High Selectivity and High Affinity for Phosphate journal, April 2003

Anion receptor chemistry: highlights from 2007 journal, January 2009

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

Controlling the Recognition and Reactivity of Alkyl Ammonium Guests Using an Anion Coordination-Based Tetrahedral Cage journal, March 2018

Tunable, shape-shifting capsule for dicarboxylates journal, January 2011

Calixpyrroles journal, January 1998

Tricyclic Host for Linear Anions journal, September 2010

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

Calix[4]pyrrole: An Old yet New Ion-Pair Receptor journal, April 2005

Recognition of Anions through NHπ Hydrogen Bonds in a Bicyclic Cyclophane—Selectivity for Nitrate journal, November 1997

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

Molecularly Mixed Composite Membranes: Challenges and Opportunities journal, March 2020

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

Small triiminopyrrolic molecular cage with high affinity and selectivity for fluoride journal, January 2019

Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity journal, January 2020

Anthracene‐Based Amido−Amine Cage Receptor for Anion Recognition under Neutral Aqueous Conditions journal, January 2020

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

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

Supramolecular Encapsulation of Tetrahedrally Hydrated Guests in a Tetrahedron Host
journal, January 2012

Anion receptor chemistry: highlights from 2010
journal, January 2012

Highly Efficient Extraction of Sulfate Ions with a Tripodal Hexaurea Receptor
journal, December 2010

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

Trapped Bifluoride
journal, March 2006

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

Non-cyclic formylated dipyrromethanes as phosphate anion receptors
journal, January 2016

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

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

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

Synthesis of 2,2′-bipyrrole-5-carboxaldehydes and their application in the synthesis of B-ring functionalized prodiginines and tambjamines
journal, September 2013

C ₃ _v Symmetric Receptors Show High Selectivity and High Affinity for Phosphate
journal, April 2003

Anion receptor chemistry: highlights from 2007
journal, January 2009

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

Controlling the Recognition and Reactivity of Alkyl Ammonium Guests Using an Anion Coordination-Based Tetrahedral Cage
journal, March 2018

Tunable, shape-shifting capsule for dicarboxylates
journal, January 2011

Calixpyrroles
journal, January 1998

Tricyclic Host for Linear Anions
journal, September 2010

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

Calix[4]pyrrole: An Old yet New Ion-Pair Receptor
journal, April 2005

Recognition of Anions through NHπ Hydrogen Bonds in a Bicyclic Cyclophane—Selectivity for Nitrate
journal, November 1997

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

Molecularly Mixed Composite Membranes: Challenges and Opportunities
journal, March 2020

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

Small triiminopyrrolic molecular cage with high affinity and selectivity for fluoride
journal, January 2019

Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity
journal, January 2020

Anthracene‐Based Amido−Amine Cage Receptor for Anion Recognition under Neutral Aqueous Conditions
journal, January 2020