Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Revealing the Hidden Costs of Organization in Host–Guest Chemistry Using Chloride-Binding Foldamers and Their Solvent Dependence

Journal Article · · Journal of the American Chemical Society
DOI:https://doi.org/10.1021/jacs.1c10758· OSTI ID:1978449

Not provided.

Research Organization:
Indiana Univ., Bloomington, IN (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
DOE Contract Number:
SC0002728
OSTI ID:
1978449
Journal Information:
Journal of the American Chemical Society, Vol. 144, Issue 3; ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English

References (115)

Anion Selectivity in Zwitterionic Amide-Functionalised Metal Salt Extractants journal July 2007
Gadolinium Complex for the Catch and Release of Phosphate from Water journal April 2017
Selective Solid-Liquid and Liquid-Liquid Extraction of Lithium Chloride Using Strapped Calix[4]pyrroles journal June 2018
Stabilization and Extraction of Fluoride Anion Using a Tetralactam Receptor journal January 2019
A Cationic Silver Pyrazine Coordination Polymer with High Capacity Anion Uptake from Water journal June 2019
Regenerable and stable sp2 carbon-conjugated covalent organic frameworks for selective detection and extraction of uranium journal January 2020
Electroactive Anion Receptor with High Affinity for Arsenate journal July 2020
Calix[4]pyrrole‐Crosslinked Porous Polymeric Networks for the Removal of Micropollutants from Water journal February 2021
Doubling the Carbonate-Binding Capacity of Nanojars by the Formation of Expanded Nanojars journal May 2021
Solid polymer electrolytes which contain tricoordinate boron for enhanced conductivity and transference numbers journal January 2013
Supramolecular Regulation of Anions Enhances Conductivity and Transference Number of Lithium in Liquid Electrolytes journal July 2018
Tetradiketone macrocycle for divalent aluminium ion batteries journal April 2021
Ion-Selective Electrodes Based on a Pyridyl-Containing Triazolophane: Altering Halide Selectivity by Combining Dipole-Promoted Cooperativity with Hydrogen Bonding journal April 2011
A mercury( ii ) ion sensor device based on an organic field effect transistor with an extended-gate modified by dipicolylamine journal January 2015
“Off-on” aggregation-based fluorescent sensor for the detection of chloride in water journal January 2015
A Bambusuril Macrocycle that Binds Anions in Water with High Affinity and Selectivity journal November 2014
Guest Back-Folding: A Molecular Design Strategy That Produces a Deep-Red Fluorescent Host/Guest Pair with Picomolar Affinity in Water journal February 2018
Di-(2-picolyl)- N- (2-quinolinylmethyl)amine-Functionalized Triarylboron: Lewis Acidity Enhancement and Fluorogenic Discrimination Between Fluoride and Cyanide in Aqueous Solution journal June 2018
Anion Recognition in Water by Charge-Neutral Halogen and Chalcogen Bonding Foldamer Receptors journal February 2019
Simple squaramide receptors for highly efficient anion binding in aqueous media and transmembrane transport journal January 2020
An Allosteric Receptor by Simultaneous “Casting” and “Molding” in a Dynamic Combinatorial Library journal November 2014
Catenation and encapsulation induce distinct reconstitutions within a dynamic library of mixed-ligand Zn 4 L 6 cages journal January 2016
Fluorogenic sensor platform for the histone code using receptors from dynamic combinatorial libraries journal January 2017
Self-templated synthesis of an orthoformate in , in -cryptand and its bridgehead inversion by dynamic covalent exchange journal January 2019
Multiple adaptation of constitutional dynamic networks and information storage in constitutional distributions of acylhydrazones journal January 2019
Glucose Binding Drives Reconfiguration of a Dynamic Library of Urea‐Containing Metal–Organic Assemblies journal January 2021
HostDesigner:  A Program for the de Novo Structure-Based Design of Molecular Receptors with Binding Sites that Complement Metal Ion Guests journal October 2002
Precedent and Theory Unite in the Hypothesis of a Highly Selective Fluoride Receptor journal April 2006
De Novo Design of Antimicrobial Polymers, Foldamers, and Small Molecules: From Discovery to Practical Applications journal January 2010
An Overlooked yet Ubiquitous Fluoride Congenitor: Binding Bifluoride in Triazolophanes Using Computer-Aided Design journal March 2014
Computer-Aided Molecular Design of Bis-phosphine Oxide Lanthanide Extractants journal February 2016
Computational Prediction and Rationalization, and Experimental Validation of Handedness Induction in Helical Aromatic Oligoamide Foldamers journal January 2017
Preorganization?From Solvents to Spherands journal December 1986
Pure CH Hydrogen Bonding to Chloride Ions: A Preorganized and Rigid Macrocyclic Receptor journal March 2008
Host-guest complexation. 35. Spherands, the first completely preorganized ligand systems journal June 1985
Rigid Macrocyclic Triamides as Anion Receptors:  Anion-Dependent Binding Stoichiometries and 1 H Chemical Shift Changes journal July 2003
A Highly Efficient, Preorganized Macrobicyclic Receptor for Halides Based on CH··· and NH···Anion Interactions journal September 2004
Computer-Aided Design of a Sulfate-Encapsulating Receptor journal May 2009
A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3]rotaxanes journal June 2013
A biomimetic receptor for glucose journal November 2018
Cucurbituril-Based Molecular Recognition journal November 2015
Cyclic Anion-Responsive π-Electronic Molecules That Overcome Energy Losses Induced by Conformation Changes journal May 2018
1,2,3-Triazole CH⋅⋅⋅Cl− Contacts Guide Anion Binding and Concomitant Folding in 1,4-Diaryl Triazole Oligomers journal May 2008
Strong, Size-Selective, and Electronically Tunable C−H···Halide Binding with Steric Control over Aggregation from Synthetically Modular, Shape-Persistent [3 4 ]Triazolophanes journal September 2008
Helicity Inversion in Responsive Foldamers Induced by Achiral Halide ion Guests journal June 2008
Flipping the Switch on Chloride Concentrations with a Light-Active Foldamer journal September 2010
Hydrophobic Collapse of Foldamer Capsules Drives Picomolar-Level Chloride Binding in Aqueous Acetonitrile Solutions journal September 2013
β-Sheet-like Hydrogen Bonds Interlock the Helical Turns of a Photoswitchable Foldamer To Enhance the Binding and Release of Chloride journal August 2014
An aryl-triazole foldamer containing a 1,8-naphthalimide fluorescent motif for monitoring and enhancing the anion-induced folding journal January 2017
Sequence-Controlled Stimuli-Responsive Single–Double Helix Conversion between 1:1 and 2:2 Chloride-Foldamer Complexes journal October 2018
Allosteric Control of Photofoldamers for Selecting between Anion Regulation and Double-to-Single Helix Switching journal November 2018
Polarity-Tolerant Chloride Binding in Foldamer Capsules by Programmed Solvent-Exclusion journal February 2021
Calix[4]pyrroles:  Old Yet New Anion-Binding Agents journal January 1996
A Calix[4]pyrrole-Based Selective Amino Acid Transporter journal November 2020
Sulfate Separation from Aqueous Alkaline Solutions by Selective Crystallization of Alkali Metal Coordination Capsules journal July 2011
Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors journal January 2014
Photocontrol of Anion Binding Affinity to a Bis-urea Receptor Derived from Stiff-Stilbene journal January 2017
Pyridine-2,6-dicarboxamide pincer-based macrocycle: a versatile ligand for oxoanions, oxometallates, and transition metals journal August 2017
Deltamides and Croconamides: Expanding the Range of Dual H-bond Donors for Selective Anion Recognition journal December 2017
Easily‐prepared Hydroxy‐containing Receptors Recognize Anions in Aqueous Media journal November 2018
Allosteric effects: structural and thermodynamic origins of binding in cooperativity in a subunit model journal October 1983
Azopyrazole-Based Photoswitchable Anion Receptor for Dihydrogen Phosphate Transport journal November 2020
Stereodivergent Anion Binding Catalysis with Molecular Motors journal January 2020
Halogen Bonding Tetraphenylethene Anion Receptors: Anion‐Induced Emissive Aggregates and Photoswitchable Recognition journal July 2021
A photoswitchable strapped calix[4]pyrrole receptor: highly effective chloride binding and release journal January 2021
Cooperative Conformational Transitions in Phenylene Ethynylene Oligomers:  Chain-Length Dependence journal April 1999
Aromatically functionalized pseudo-crown ethers with unusual solvent response and enhanced binding properties journal January 2018
Intramolecular Hydrogen Bonds Preorganize an Aryl-triazole Receptor into a Crescent for Chloride Binding journal May 2010
Modular tripodal receptors for the hydrosulfide (HS ) anion journal January 2018
The Influence of Binding Site Geometry on Anion‐Binding Selectivity: A Case Study of Macrocyclic Receptors Built on the Azulene Skeleton journal July 2018
Solvatochromism and fluorescence response of a halogen bonding anion receptor journal January 2018
Anion-Responsive π-Electronic Systems Exhibiting Diverse Conformations and Stoichiometries in Anion Binding: Anion-Responsive π-Electronic Systems Exhibiting Diverse Conformations and Stoichiometries in Anion Binding journal May 2020
The chelate effect in binding, catalysis, and chemotherapy journal January 2000
The Design of Molecular Hosts, Guests, and Their Complexes (Nobel Lecture) journal August 1988
Cryptates: the chemistry of macropolycyclic inclusion complexes journal February 1978
Ligand Binding Energy and Catalytic Efficiency from Improved Packing within Receptors and Enzymes journal May 2003
Supramolecular Chelation Based on Folding journal March 2005
Dramatic Enhancement of Binding Affinities Between Foldamer‐Based Receptors and Anions by Intra‐Receptor π‐Stacking journal April 2020
Designing Helical Molecular Capsules Based on Folded Aromatic Amide Oligomers journal March 2018
Enhancing Binding Affinity by the Cooperativity between Host Conformation and Host–Guest Interactions journal June 2011
Cooperatively Enhanced Receptors for Biomimetic Molecular Recognition journal October 2013
Rationally Designed Cooperatively Enhanced Receptors To Magnify Host–Guest Binding in Water journal January 2015
Solvophobically Driven Folding of Nonbiological Oligomers journal September 1997
1,3,5-2,4,6-Functionalized, Facially Segregated Benzenes—Exploitation of Sterically Predisposed Systems in Supramolecular Chemistry journal May 2002
(How) does 1,3,5-triethylbenzene scaffolding work? Analyzing the abilities of 1,3,5-triethylbenzene- and 1,3,5-trimethylbenzene-based scaffolds to preorganize the binding elements of supramolecular hosts and to improve binding of targets journal January 2012
A Folded, Secondary Structure in Step-Growth Oligomers from Covalently Linked, Crowded Aromatics journal March 2003
Supramolecular Chemistry book January 2009
A Combined Charge and Energy Decomposition Scheme for Bond Analysis journal March 2009
In Silico Design of Cylindrophanes: The Role of Functional Groups in a Fluoride Selective Host journal August 2020
Conformational Features and Anion-Binding Properties of Calix[4]pyrrole:  A Theoretical Study journal June 2001
Strong CH⋅⋅⋅Halide Hydrogen Bonds from 1,2,3-Triazoles Quantified Using Pre-Organized and Shape-Persistent Triazolophanes journal October 2009
Large Scale Affinity Calculations of Cyclodextrin Host–Guest Complexes: Understanding the Role of Reorganization in the Molecular Recognition Process journal June 2013
Fluorinated macrocyclic ethers as fluoride ion hosts. Novel structures and dynamic properties journal October 1990
Two levels of conformational pre-organization consolidate strong CH hydrogen bonds in chloride–triazolophane complexes journal January 2011
Anion Binding in Solution: Beyond the Electrostatic Regime journal September 2017
Polar solvent effects on tartaric acid binding by aromatic oligoamide foldamer capsules journal January 2016
Entropy/Enthalpy Compensation in Anion Binding: Biotin[6]uril and Biotin- l -sulfoxide[6]uril Reveal Strong Solvent Dependency journal February 2019
Solvent-Dependent Linear Free-Energy Relationship in a Flexible Host–Guest System journal September 2020
Oligomeric Cholates:  Amphiphilic Foldamers with Nanometer-Sized Hydrophilic Cavities journal November 2005
Foldamers:  A Manifesto journal April 1998
A Field Guide to Foldamers journal December 2001
Parameters of helix-coil transition theory for alanine-based peptides of varying chain lengths in water journal November 1991
Linear extrapolation method of analyzing solvent denaturation curves journal January 2000
Anion binding of a neutral bis(cyclopeptide) in water–methanol mixtures containing up to 95% water journal January 2014
Nuclear Magnetic Resonance as a Tool for Determining Protonation Constants of Natural Polyprotic Bases in Solution journal November 1995
Detailed Spectroscopic, Thermodynamic, and Kinetic Characterization of Nickel(II) Complexes with 2,2‘-Bipyridine and 1,10-Phenanthroline Attained via Equilibrium-Restricted Factor Analysis journal January 2008
Aromatic and Aliphatic CH Hydrogen Bonds Fight for Chloride while Competing Alongside Ion Pairing within Triazolophanes journal November 2010
Electrostatic and Allosteric Cooperativity in Ion-Pair Binding: A Quantitative and Coupled Experiment–Theory Study with Aryl–Triazole–Ether Macrocycles journal July 2015
Anions Stabilize Each Other inside Macrocyclic Hosts journal October 2016
Influence of the Attachment of a Gold(I) Phosphine Moiety at the Upper Rim of a Calix[4]pyrrole on the Binding of Tetraalkylammonium Chloride Salts journal March 2020
A test of the linear extrapolation of unfolding free energy changes over an extended denaturant concentration range journal May 1992
Biophysical Characterization of the Olfactomedin Domain of Myocilin, an Extracellular Matrix Protein Implicated in Inherited Forms of Glaucoma journal January 2011
The role of statistics and microenvironment for the photoresponse in multi-switch architectures: The case of photoswitchable oligoazobenzene foldamers journal January 2013
Predicting the energetics of osmolyte-induced protein folding/unfolding journal October 2005
Conformational Selection in Anion Recognition: cGMP-Selective Binding by a Naphthalimide-Functionalized Amido-Amine Macrocycle journal May 2019