Anionic Templates Drive Conversion Between a ZnL Tricapped Trigonal Prism and ZnL Pseudo-Octahedra

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2023 Jul 13

PMID 37440669

Authors

Hua-Kui Liu

Tanya K Ronson

Kai Wu

Dong Luo

Jonathan R Nitschke

Affiliations

Soon will be listed here.

Abstract

This work introduces the use of 8-aminoquinoline subcomponents to generate complex three-dimensional structures. Together with a tris(formylpyridine), 8-aminoquinoline condensed around Zn templates to produce a tris(tridentate) ligand. This ligand is incorporated into either a tricapped trigonal prismatic ZnL structure or a pair of pseudo-octahedral ZnL diastereomers, with and symmetries. Introduction of a methyl group onto the aminoquinoline modulated the coordination sphere of Zn, which favored the ZnL structure and disfavored the ZnL assembly. The tricapped trigonal prismatic ZnL architecture converted into a single ZnL cage diastereomer following the addition of a dianionic 4,4'-dinitrostilbene-2,2'-disulfonate guest. Four of these guests clustered tightly at the four windows of the ZnL cage, held in place through electrostatic interactions and hydrogen bonding, stabilize a single diastereomeric configuration with symmetry.

Citing Articles

Evolution from [Zn] to a record-high [Zn] subblock and engineering a hierarchical supramolecular framework for enhanced iodine uptake.

Tao Y, Dong Q, Wan J, Huang F, Duan J, Zeng M Chem Sci. 2024; 16(4):1730-1736.

PMID: 39677939 PMC: 11639904. DOI: 10.1039/d4sc04474f.

A CuL Cage Dynamically Reconfigures to Form Suit[4]anes and Selectively Bind Fluorinated Steroids.

Speakman N, Heard A, Nitschke J J Am Chem Soc. 2024; 146(15):10234-10239.

PMID: 38578086 PMC: 11027141. DOI: 10.1021/jacs.4c00257.

References

Anhauser J, Puttreddy R, Glanz L, Schneider A, Engeser M, Rissanen K . Subcomponent Self-Assembly of a Cyclic Tetranuclear Fe Helicate in a Highly Diastereoselective Self-Sorting Manner. Chemistry. 2019; 25(53):12294-12297. PMC: 6790559. DOI: 10.1002/chem.201903164. View

Yamashina M, Sei Y, Akita M, Yoshizawa M . Safe storage of radical initiators within a polyaromatic nanocapsule. Nat Commun. 2014; 5:4662. DOI: 10.1038/ncomms5662. View

Lewing D, Koppetz H, Hahn F . Reversible Formation and Transmetalation of Schiff-Base Complexes in Subcomponent Self-Assembly Reactions. Inorg Chem. 2015; 54(15):7653-9. DOI: 10.1021/acs.inorgchem.5b01334. View

Zarra S, Clegg J, Nitschke J . Selective assembly and disassembly of a water-soluble Fe10L15 prism. Angew Chem Int Ed Engl. 2013; 52(18):4837-40. DOI: 10.1002/anie.201209694. View

Rizzuto F, Carpenter J, Nitschke J . Multisite Binding of Drugs and Natural Products in an Entropically Favorable, Heteroleptic Receptor. J Am Chem Soc. 2019; 141(22):9087-9095. DOI: 10.1021/jacs.9b03776. View

Carpenter J, McTernan C, Ronson T, Nitschke J . Anion Pairs Template a Trigonal Prism with Disilver Vertices. J Am Chem Soc. 2019; 141(29):11409-11413. PMC: 6756586. DOI: 10.1021/jacs.9b05432. View

Howson S, Bolhuis A, Brabec V, Clarkson G, Malina J, Rodger A . Optically pure, water-stable metallo-helical 'flexicate' assemblies with antibiotic activity. Nat Chem. 2011; 4(1):31-6. DOI: 10.1038/nchem.1206. View

Zhang D, Ronson T, Guryel S, Thoburn J, Wales D, Nitschke J . Temperature Controls Guest Uptake and Release from ZnL Tetrahedra. J Am Chem Soc. 2019; 141(37):14534-14538. PMC: 6753657. DOI: 10.1021/jacs.9b07307. View

Takezawa H, Shitozawa K, Fujita M . Enhanced reactivity of twisted amides inside a molecular cage. Nat Chem. 2020; 12(6):574-578. DOI: 10.1038/s41557-020-0455-y. View

10.

Riddell I, Smulders M, Clegg J, Hristova Y, Breiner B, Thoburn J . Anion-induced reconstitution of a self-assembling system to express a chloride-binding Co10L15 pentagonal prism. Nat Chem. 2012; 4(9):751-6. DOI: 10.1038/nchem.1407. View

11.

Dhamija A, Gunnam A, Yu X, Lee H, Hwang I, Ko Y . Dramatically Enhanced Reactivity of Fullerenes and Tetrazine towards the Inverse-Electron-Demand Diels-Alder Reaction inside a Porous Porphyrinic Cage. Angew Chem Int Ed Engl. 2022; 61(44):e202209326. DOI: 10.1002/anie.202209326. View

12.

Chepelin O, Ujma J, Wu X, Slawin A, Pitak M, Coles S . Luminescent, enantiopure, phenylatopyridine iridium-based coordination capsules. J Am Chem Soc. 2012; 134(47):19334-7. DOI: 10.1021/ja309031h. View

13.

Fu J, Zheng B, Zhang H, Zhao Y, Zhang D, Zhang W . Chirality transcription in the anion-coordination-driven assembly of tetrahedral cages. Chem Commun (Camb). 2020; 56(16):2475-2478. DOI: 10.1039/c9cc09752j. View

14.

Tessarolo J, Lee H, Sakuda E, Umakoshi K, Clever G . Integrative Assembly of Heteroleptic Tetrahedra Controlled by Backbone Steric Bulk. J Am Chem Soc. 2021; 143(17):6339-6344. PMC: 8154538. DOI: 10.1021/jacs.1c01931. View

15.

Zhou X, Wu Y, Li D . Polyhedral metal-imidazolate cages: control of self-assembly and cage to cage transformation. J Am Chem Soc. 2013; 135(43):16062-5. DOI: 10.1021/ja4092984. View

16.

Ren D, Qiu D, Pang C, Li Z, Gu Z . Chiral tetrahedral iron(II) cages: diastereoselective subcomponent self-assembly, structure interconversion and spin-crossover properties. Chem Commun (Camb). 2014; 51(4):788-91. DOI: 10.1039/c4cc08041f. View

17.

Saha R, Ghosh A, Samajdar R, Mukherjee P . Self-Assembled Pd Molecular Spheroids and Their Proton Conduction Property. Inorg Chem. 2018; 57(11):6540-6548. DOI: 10.1021/acs.inorgchem.8b00668. View

18.

Gadzikwa T, Bellini R, Dekker H, Reek J . Self-assembly of a confined rhodium catalyst for asymmetric hydroformylation of unfunctionalized internal alkenes. J Am Chem Soc. 2012; 134(6):2860-3. DOI: 10.1021/ja211455j. View

19.

Zhang D, Ronson T, Mosquera J, Martinez A, Guy L, Nitschke J . Anion Binding in Water Drives Structural Adaptation in an Azaphosphatrane-Functionalized FeL Tetrahedron. J Am Chem Soc. 2017; 139(19):6574-6577. DOI: 10.1021/jacs.7b02950. View

20.

Bao S, Xu Z, Ju Y, Song Y, Wang H, Niu Z . The Covalent and Coordination Co-Driven Assembly of Supramolecular Octahedral Cages with Controllable Degree of Distortion. J Am Chem Soc. 2020; 142(31):13356-13361. DOI: 10.1021/jacs.0c07014. View