A Flexible Self-folding Receptor for Coronene

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2020 Feb 29

PMID 32110323

Citations 2

Authors

David Lozano

Ruben Alvarez-Yebra

Ricard Lopez-Coll

Agusti Lledo

Affiliations

Soon will be listed here.

Abstract

We report a conformationally flexible deep cavitand receptor based on calix[5]arene and stabilized by a cooperative network of hydrogen bonds. The receptor binds coronene selectively over smaller polycyclic aromatic hydrocarbons, but is flexible enough to adapt to a smaller guest that presents a complementary electron deficient surface. The unique dynamic properties of this system have been thoroughly studied by NMR spectroscopy and molecular dynamics (MD) simulations.

Citing Articles

Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand.

Alvarez-Yebra R, Lopez-Coll R, Galan-Masferrer P, Lledo A Org Lett. 2023; 25(18):3190-3194.

PMID: 37038894 PMC: 10186369. DOI: 10.1021/acs.orglett.3c00463.

A contorted nanographene shelter.

Wu H, Wang Y, Song B, Wang H, Zhou J, Sun Y Nat Commun. 2021; 12(1):5191.

PMID: 34465772 PMC: 8408160. DOI: 10.1038/s41467-021-25255-6.

References

Wu J, Pisula W, Mullen K . Graphenes as potential material for electronics. Chem Rev. 2007; 107(3):718-47. DOI: 10.1021/cr068010r. View

Purse B, Ballester P, Rebek Jr J . Reactivity and molecular recognition: amine methylation by an introverted ester. J Am Chem Soc. 2003; 125(48):14682-3. DOI: 10.1021/ja036595q. View

Pasquale S, Sattin S, Escudero-Adan E, Martinez-Belmonte M, de Mendoza J . Giant regular polyhedra from calixarene carboxylates and uranyl. Nat Commun. 2012; 3:785. PMC: 3337980. DOI: 10.1038/ncomms1793. View

Samanta J, Natarajan R . Cofacial Organic Click Cage to Intercalate Polycyclic Aromatic Hydrocarbons. Org Lett. 2016; 18(14):3394-7. DOI: 10.1021/acs.orglett.6b01554. View

Mullen K, Rabe J . Nanographenes as active components of single-molecule electronics and how a scanning tunneling microscope puts them to work. Acc Chem Res. 2008; 41(4):511-20. DOI: 10.1021/ar7001446. View

Hooley R, Rebek Jr J . Deep cavitands provide organized solvation of reactions. J Am Chem Soc. 2005; 127(34):11904-5. DOI: 10.1021/ja052910s. View

Wohrle T, Wurzbach I, Kirres J, Kostidou A, Kapernaum N, Litterscheidt J . Discotic Liquid Crystals. Chem Rev. 2015; 116(3):1139-241. DOI: 10.1021/acs.chemrev.5b00190. View

Hooley R, Rebek Jr J . Chemistry and catalysis in functional cavitands. Chem Biol. 2009; 16(3):255-64. PMC: 2661873. DOI: 10.1016/j.chembiol.2008.09.015. View

Barnes J, Juricek M, Strutt N, Frasconi M, Sampath S, Giesener M . ExBox: a polycyclic aromatic hydrocarbon scavenger. J Am Chem Soc. 2012; 135(1):183-92. DOI: 10.1021/ja307360n. View

10.

Srogi K . Monitoring of environmental exposure to polycyclic aromatic hydrocarbons: a review. Environ Chem Lett. 2017; 5(4):169-195. PMC: 5614912. DOI: 10.1007/s10311-007-0095-0. View

11.

Lledo A . Complementary Binding in Urea-Based Self-Folding Cavitands. Org Lett. 2015; 17(15):3770-3. DOI: 10.1021/acs.orglett.5b01747. View

12.

Garcia-Hartjes J, Bernardi S, Weijers C, Wennekes T, Gilbert M, Sansone F . Picomolar inhibition of cholera toxin by a pentavalent ganglioside GM1os-calix[5]arene. Org Biomol Chem. 2013; 11(26):4340-9. DOI: 10.1039/c3ob40515j. View

13.

Hibbert D, Thordarson P . The death of the Job plot, transparency, open science and online tools, uncertainty estimation methods and other developments in supramolecular chemistry data analysis. Chem Commun (Camb). 2016; 52(87):12792-12805. DOI: 10.1039/c6cc03888c. View

14.

Pinalli R, Pedrini A, Dalcanale E . Biochemical sensing with macrocyclic receptors. Chem Soc Rev. 2018; 47(18):7006-7026. DOI: 10.1039/c8cs00271a. View

15.

Dale E, Vermeulen N, Thomas A, Barnes J, Juricek M, Blackburn A . ExCage. J Am Chem Soc. 2014; 136(30):10669-82. DOI: 10.1021/ja5041557. View

16.

Ibanez S, Peris E . A Rigid Trigonal-Prismatic Hexagold Metallocage That Behaves as a Coronene Trap. Angew Chem Int Ed Engl. 2019; 58(20):6693-6697. DOI: 10.1002/anie.201902568. View

17.

Ringe D, Petsko G . Biochemistry. How enzymes work. Science. 2008; 320(5882):1428-9. DOI: 10.1126/science.1159747. View

18.

Pinacho Crisostomo F, Lledo A, Shenoy S, Iwasawa T, Rebek Jr J . Recognition and organocatalysis with a synthetic cavitand receptor. J Am Chem Soc. 2009; 131(21):7402-10. PMC: 2720318. DOI: 10.1021/ja900766b. View

19.

Raynal M, Ballester P, Vidal-Ferran A, van Leeuwen P . Supramolecular catalysis. Part 2: artificial enzyme mimics. Chem Soc Rev. 2013; 43(5):1734-87. DOI: 10.1039/c3cs60037h. View