Salen-Based Amphiphiles: Directing Self-Assembly in Water by Metal Complexation

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2019 Aug 8

PMID 31389650

Citations 3

Authors

Filippo Tosi

Marc C A Stuart

Sander J Wezenberg

Ben L Feringa

Affiliations

Soon will be listed here.

Abstract

Tuning morphologies of self-assembled structures in water is a major challenge. Herein we present a salen-based amphiphile which, using complexation with distinct transition metal ions, allows to control effectively the self-assembly morphology in water, as observed by Cryo-TEM and confirmed by DLS measurements. Applying this strategy with various metal ions gives a broad spectrum of self-assembled structures starting from the same amphiphilic ligand (from cubic structures to vesicles and micelles). Thermogravimetric analysis and electric conductivity measurements reveal a key role for water coordination apparently being responsible for the distinct assembly behavior.

Citing Articles

Self-assembly of reversed bilayer vesicles through pnictogen bonding: water-stable supramolecular nanocontainers for organic solvents.

Moaven S, Watson B, Thompson S, Lyons V, Unruh D, Casadonte D Chem Sci. 2020; 11(17):4374-4380.

PMID: 33224458 PMC: 7659706. DOI: 10.1039/d0sc00206b.

Tuning of Morphology by Chirality in Self-Assembled Structures of Bis(Urea) Amphiphiles in Water.

Tosi F, Berrocal J, Stuart M, Wezenberg S, Feringa B Chemistry. 2020; 27(1):326-330.

PMID: 32785999 PMC: 7839493. DOI: 10.1002/chem.202003403.

Salen-Based Amphiphiles: Directing Self-Assembly in Water by Metal Complexation.

Tosi F, Stuart M, Wezenberg S, Feringa B Angew Chem Int Ed Engl. 2019; 58(42):14935-14939.

PMID: 31389650 PMC: 6899911. DOI: 10.1002/anie.201908010.

References

Percec V, Leowanawat P, Sun H, Kulikov O, Nusbaum C, Tran T . Modular synthesis of amphiphilic Janus glycodendrimers and their self-assembly into glycodendrimersomes and other complex architectures with bioactivity to biomedically relevant lectins. J Am Chem Soc. 2013; 135(24):9055-77. DOI: 10.1021/ja403323y. View

Li G, Yu W, Ni J, Liu T, Liu Y, Sheng E . Self-assembly of a homochiral nanoscale metallacycle from a metallosalen complex for enantioselective separation. Angew Chem Int Ed Engl. 2008; 47(7):1245-9. DOI: 10.1002/anie.200704347. View

Macdonald R, Ashley G, Shida M, Rakhmanova V, Tarahovsky Y, Pantazatos D . Physical and biological properties of cationic triesters of phosphatidylcholine. Biophys J. 1999; 77(5):2612-29. PMC: 1300535. DOI: 10.1016/S0006-3495(99)77095-5. View

Palmer L, Stupp S . Molecular self-assembly into one-dimensional nanostructures. Acc Chem Res. 2008; 41(12):1674-84. PMC: 2645948. DOI: 10.1021/ar8000926. View

Martinez D, Motevalli M, Watkinson M . Aquachloro[N,N'-ethylenebis(salicylideneiminato)]manganese(III). Acta Crystallogr C. 2002; 58(Pt 4):M258-60. DOI: 10.1107/s0108270102003529. View

Jiang J, MacLachlan M . Cationic guest inclusion in widemouthed Schiff base macrocycles. Chem Commun (Camb). 2009; (38):5695-7. DOI: 10.1039/b914564h. View

Coleman A, Beierle J, Stuart M, Macia B, Caroli G, Mika J . Light-induced disassembly of self-assembled vesicle-capped nanotubes observed in real time. Nat Nanotechnol. 2011; 6(9):547-52. DOI: 10.1038/nnano.2011.120. View

Elemans J, Wezenberg S, Coenen M, Escudero-Adan E, Benet-Buchholz J, den Boer D . Axial ligand control over monolayer and bilayer formation of metal-salophens at the liquid-solid interface. Chem Commun (Camb). 2010; 46(15):2548-50. DOI: 10.1039/b922212j. View

Dwars T, Paetzold E, Oehme G . Reactions in micellar systems. Angew Chem Int Ed Engl. 2005; 44(44):7174-99. DOI: 10.1002/anie.200501365. View

10.

Kleij A, Kuil M, Tooke D, Lutz M, Spek A, Reek J . Zn(II)-salphen complexes as versatile building blocks for the construction of supramolecular box assemblies. Chemistry. 2005; 11(16):4743-50. DOI: 10.1002/chem.200500227. View

11.

Jonsson S, Odille F, Norrby P, Warnmark K . Modulation of the reactivity, stability and substrate- and enantioselectivity of an epoxidation catalyst by noncovalent dynamic attachment of a receptor functionality--aspects on the mechanism of the Jacobsen-Katsuki epoxidation applied to a.... Org Biomol Chem. 2006; 4(10):1927-48. DOI: 10.1039/b518244a. View

12.

Fuji K, Morimoto T, Tsutsumi K, Kakiuchi K . Aqueous catalytic Pauson-Khand-type reactions of enynes with formaldehyde: transfer carbonylation involving an aqueous decarbonylation and a micellar carbonylation. Angew Chem Int Ed Engl. 2003; 42(21):2409-11. DOI: 10.1002/anie.200351384. View

13.

Li L, Feng X, Cui X, Ma Y, Ding S, Wang W . Salen-Based Covalent Organic Framework. J Am Chem Soc. 2017; 139(17):6042-6045. DOI: 10.1021/jacs.7b01523. View

14.

Consiglio G, Failla S, Finocchiaro P, Oliveri I, Purrello R, Di Bella S . Supramolecular aggregation/deaggregation in amphiphilic dipolar Schiff-base zinc(II) complexes. Inorg Chem. 2010; 49(11):5134-42. DOI: 10.1021/ic100284r. View

15.

Hui J, MacLachlan M . Fibrous aggregates from dinuclear zinc(II) salphen complexes. Dalton Trans. 2010; 39(31):7310-9. DOI: 10.1039/c0dt00234h. View

16.

Chen J, Leung F, Stuart M, Kajitani T, Fukushima T, Van der Giessen E . Artificial muscle-like function from hierarchical supramolecular assembly of photoresponsive molecular motors. Nat Chem. 2018; 10(2):132-138. DOI: 10.1038/nchem.2887. View

17.

Barclay T, Constantopoulos K, Matisons J . Nanotubes self-assembled from amphiphilic molecules via helical intermediates. Chem Rev. 2014; 114(20):10217-91. DOI: 10.1021/cr400085m. View

18.

Van Esch J, Roks M, Nolte R . Membrane-bound cytochrome P-450 mimic. Polymerized vesicles as microreactors. J Am Chem Soc. 2011; 108(19):6093-4. DOI: 10.1021/ja00279a098. View

19.

Kleij A, Kuil M, Tooke D, Spek A, Reek J . Metal-directed self-assembly of a Zn(II)-salpyr complex into a supramolecular vase structure. Inorg Chem. 2007; 46(15):5829-31. DOI: 10.1021/ic700408v. View

20.

Shultz A, Farha O, Adhikari D, Sarjeant A, Hupp J, Nguyen S . Selective surface and near-surface modification of a noncatenated, catalytically active metal-organic framework material based on Mn(salen) struts. Inorg Chem. 2011; 50(8):3174-6. DOI: 10.1021/ic101952y. View