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:: Mon Aug 12 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); 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.

Copy to clipboard


                    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

Copy to clipboard


                    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.

Copy to clipboard


                    
@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         = {Mon Aug 12 00:00:00 EDT 2019},

  month        = {Mon Aug 12 00:00:00 EDT 2019}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Accepted Manuscript (DOE)

Publisher's Version of Record

https://doi.org/10.1039/C9CC05613K

Other availability

Search WorldCat to find libraries that may hold this journal

Citation Metrics:

Cited by: 26 works

Citation information provided by
Web of Science

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.

All figures and tables (6 total)

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

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

Ripa, Louis W.
Journal of Public Health Dentistry, Vol. 53, Issue 1
DOI: 10.1111/j.1752-7325.1993.tb02666.x

Systematic review of water fluoridation
journal, October 2000

McDonagh, M. S.
BMJ, Vol. 321, Issue 7265
DOI: 10.1136/bmj.321.7265.855

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

Carstairs, Catherine; Elder, Rachel
Canadian Historical Review, Vol. 89, Issue 3
DOI: 10.3138/chr.89.3.345

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

Kleerekoper, Michael
Endocrinology and Metabolism Clinics of North America, Vol. 27, Issue 2
DOI: 10.1016/S0889-8529(05)70015-3

Determination of urinary fluoride by ion chromatography
journal, March 1993

Michigami, Yoshimasa; Kuroda, Yasuyoshi; Ueda, Kazumasa
Analytica Chimica Acta, Vol. 274, Issue 2
DOI: 10.1016/0003-2670(93)80479-5

Developmental neurotoxicity of industrial chemicals
journal, December 2006

Grandjean, P.; Landrigan, Pj
The Lancet, Vol. 368, Issue 9553
DOI: 10.1016/S0140-6736(06)69665-7

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

Friesen, Melissa C.; Benke, Geza; Del Monaco, Anthony
Cancer Causes & Control, Vol. 20, Issue 6
DOI: 10.1007/s10552-009-9329-8

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

Gazzano, E.; Bergandi, L.; Riganti, C.
Current Medicinal Chemistry, Vol. 17, Issue 22
DOI: 10.2174/092986710791698503

Molecular mechanisms of fluoride toxicity
journal, November 2010

Barbier, Olivier; Arreola-Mendoza, Laura; Del Razo, Luz María
Chemico-Biological Interactions, Vol. 188, Issue 2
DOI: 10.1016/j.cbi.2010.07.011

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

Sandhu, R.; Lal, H.; Kundu, Z. S.
Biological Trace Element Research, Vol. 144, Issue 1-3
DOI: 10.1007/s12011-009-8382-1

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

Zhou, Ying; Zhang, Jun Feng; Yoon, Juyoung
Chemical Reviews, Vol. 114, Issue 10
DOI: 10.1021/cr400352m

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

Wade, Casey R.; Broomsgrove, Alexander E. J.; Aldridge, Simon
Chemical Reviews, Vol. 110, Issue 7
DOI: 10.1021/cr900401a

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

Cametti, Massimo; Rissanen, Kari
Chem. Soc. Rev., Vol. 42, Issue 5
DOI: 10.1039/C2CS35439J

Recognition and sensing of fluoride anion
journal, January 2009

Cametti, Massimo; Rissanen, Kari
Chemical Communications, Issue 20
DOI: 10.1039/b902069a

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

Brugnara, Andrea; Topić, Filip; Rissanen, Kari
Chem. Sci., Vol. 5, Issue 10
DOI: 10.1039/C4SC01457J

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

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

Samanta, Ritwik; Kumar, B. Sathish; Panda, Pradeepta K.
Organic Letters, Vol. 17, Issue 17
DOI: 10.1021/acs.orglett.5b01866

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

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

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

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

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

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

Tricyclic Host for Linear Anions
journal, September 2010

Kang, Sung Ok; Day, Victor W.; Bowman-James, Kristin
Inorganic Chemistry, Vol. 49, Issue 18
DOI: 10.1021/ic1013297

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

Kang, Sung Ok; VanderVelde, David; Powell, Douglas
Journal of the American Chemical Society, Vol. 126, Issue 39
DOI: 10.1021/ja046078n

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

Kang, Sung Ok; Powell, Douglas; Bowman-James, Kristin
Journal of the American Chemical Society, Vol. 127, Issue 39
DOI: 10.1021/ja054332l

Trapped Bifluoride
journal, March 2006

Kang, Sung Ok; Powell, Douglas; Day, Victor W.
Angewandte Chemie International Edition, Vol. 45, Issue 12
DOI: 10.1002/anie.200504066

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

Lopez, N.; Graham, D. J.; McGuire, R.
Science, Vol. 335, Issue 6067
DOI: 10.1126/science.1212678

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

Hong, Seong-Jin; Yoo, Jaeduk; Jeong, Seung-Doo
Journal of Inclusion Phenomena and Macrocyclic Chemistry, Vol. 66, Issue 1-2
DOI: 10.1007/s10847-009-9700-0

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

Bill, Nathan L.; Kim, Dae-Sik; Kim, Sung Kuk
Supramolecular Chemistry, Vol. 24, Issue 1
DOI: 10.1080/10610278.2011.622392

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

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

Cacciarini, Martina; Nativi, Cristina; Norcini, Martina
Org. Biomol. Chem., Vol. 9, Issue 4
DOI: 10.1039/C0OB00651C

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

Yin, Ying; Sarma, Tridib; Wang, Fei
Organic Letters, Vol. 21, Issue 6
DOI: 10.1021/acs.orglett.9b00445

Trapped Bifluoride
journal, March 2006

Kang, Sung Ok; Powell, Douglas; Day, Victor W.
Angewandte Chemie, Vol. 118, Issue 12
DOI: 10.1002/ange.200504066

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

Martinez-Manez, Ramon; Sancenon, Felix
ChemInform, Vol. 35, Issue 6
DOI: 10.1002/chin.200406298

Developmental neurotoxicity of industrial chemicals
journal, March 2007

Saunders, Norman R.; Dziegielewska, Katarzyna M.
The Lancet, Vol. 369, Issue 9564
DOI: 10.1016/s0140-6736(07)60397-3

Amide-Based Ligands for Anion Coordination
journal, March 2007

Kang, Sung Ok; Begum, Rowshan Ara; Bowman-James, Kristin
ChemInform, Vol. 38, Issue 12
DOI: 10.1002/chin.200712244

Works referencing / citing this record:

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

Bairagya, Monojit Das; Bujol, Ryan J.; Elgrishi, Noémie
Chemistry – A European Journal
DOI: 10.1002/chem.201904499

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

Morozov, Boris S.; Namashivaya, Siva S. R.; Zakharko, Marina A.
ChemistryOpen, Vol. 9, Issue 2
DOI: 10.1002/open.201900309

Figures / Tables found in this record:

Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.

Similar Records in DOE PAGES and OSTI.GOV collections:

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

Journal Article Oh, Ju Hyun ; Kim, Jeong Hyeon ; Kim, Dong Sub ; ... - Organic Letters

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
Cited by 29
https://doi.org/10.1021/acs.orglett.9b01515

Full Text Available
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

Here, 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. Asmore »« less
Cited by 7
https://doi.org/10.1021/acs.joc.7b03135

Full Text Available
Soft Materials Constructed Using Calix[4]pyrrole- and “Texas-Sized” Box-Based Anion Receptors

Journal Article Ji, Xiaofan ; Chi, Xiaodong ; Ahmed, Mehroz ; ... - Accounts of Chemical Research

We present that soft materials have received considerable attention from supramolecular chemists and material scientists alike. This interest reflects the advantages provided by their soft, flexible nature and the convenience of the molecular self-assembly that underlies their preparation. Common soft supramolecular materials include polymeric gels, supramolecular polymers, nanoaggregates, and membranes. Polymeric gels are solidlike networks of cross-linked polymer chains. Supramolecular polymers contain repeat units connected through reversible non-covalent bonds. Nanoaggregates are formed as a result of hydrophobic interactions involving amphiphilic building blocks. Because of the presence of non-covalent interactions, supramolecular soft materials typically display stimuli-responsive or adaptive features. Various macrocyclicmore »« less
Cited by 53
https://doi.org/10.1021/acs.accounts.9b00187

Full Text Available
Macrocycles as Ion Pair Receptors

Journal Article He, Qing ; Vargas-Zúñiga, Gabriela I. ; Kim, Seung Hyun ; ... - Chemical Reviews

Cation and anion recognition have both played central roles in the development of supramolecular chemistry. Additionally, much of the associated research has focused on the development of receptors for individual cations or anions, as well as their applications in different areas. Rarely is complexation of the counterions considered. In contrast, ion pair recognition chemistry, emerging from cation and anion coordination chemistry, is a specific research field where co-complexation of both anions and cations, so-called ion pairs, is the center of focus. Systems used for the purpose, known as ion pair receptors, are typically di- or polytopic hosts that contain recognitionmore »« less
Cited by 183
https://doi.org/10.1021/acs.chemrev.8b00734

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

Journal Article Heo, Nam Jung ; Oh, Ju Hyun ; Lee, Jeong Tae ; ... - Organic Chemistry Frontiers (Online)

Calix[4]pyrroles 1 and 2, diametrically strapped with a phenanthroline via ester and amide linkages, respectively, have been synthesized as anion receptors. It was revealed by ¹H NMR spectroscopic analysis that receptors 1 and 2 possessing both hydrogen bonding donors and acceptors were able to bind the bicarbonate anion (as its tetraethylammonium (TEA⁺) or sodium salt) in CDCl₃, as well as in 15% aqueous DMSO with high affinity and selectivity over other anions. The amide-based receptor 2 contains additional potential hydrogen bonding donors relative to its ester-based congener 1. Nevertheless, in CDCl₃ receptor 1 was found to display a higher affinitymore »« less
Cited by 8
https://doi.org/10.1039/c9qo01377f

Full Text Available

Similar Records

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

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

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