Diastereoselective Control of Tetraphenylethene Reactivity by Metal Template Self-Assembly
Journal article, 2019

The reaction of 4,4′,4′′,4′′′-(ethene-1,1,2,2-tetrayl)tetraaniline with 2-pyridinecarboxaldehyde and iron(II) chloride resulted, after aqueous workup, in the diastereoselective formation of an [Fe 2 L 3 ] 4+ triple-stranded helicate structure, irrespective of the stoichiometry employed. The helicate structure was characterized in solution by multinuclear NMR spectroscopy, and in the solid state by single-crystal X-ray crystallography. The reaction of iron(II) tetrafluoroborate or iron(II) bistriflimide with the tetraaniline and 2-pyridinecarboxaldehyde allowed the formation of an [Fe 8 L 6 ] 16+ cube when the appropriate stoichiometry was used, but these structures were unstable with respect to hydrolysis. The pendant amine groups on the helicate can be functionalized by reaction with acid chlorides or anhydrides, and the resulting functionalized tetraphenylethene (TPE) units were isolated by the reaction of the helicate with tris(2-aminoethyl)amine. The emission properties of the TPE units were studied in THF/water mixtures, and they were found by dynamic light scattering to self-assemble into large (av. diameter 250 nm) structures.

self-assembly

metal template synthesis

helicates

fluorescence

iron

Author

Aaron D.W. Kennedy

University of New South Wales (UNSW)

Nicholas de Haas

University of New South Wales (UNSW)

Hasti Iranmanesh

University of New South Wales (UNSW)

Ena T. Luis

University of New South Wales (UNSW)

Chao Shen

University of New South Wales (UNSW)

Pi Wang

Zhejiang University

University of New South Wales (UNSW)

Jason R. Price

Australian Synchrotron (ANSTO)

William A. Donald

University of New South Wales (UNSW)

Joakim Andreasson

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry

Feihe Huang

Zhejiang University

J. E. Beves

University of New South Wales (UNSW)

Chemistry - A European Journal

0947-6539 (ISSN) 1521-3765 (eISSN)

Vol. 25 22 5708-5718

Subject Categories

Chemical Sciences

DOI

10.1002/chem.201806259

PubMed

30775812

More information

Latest update

5/14/2019