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229
A Divalent Pentastable Redox-Switchable Donor-Acceptor Rotaxane

H.V. Schröder, H. Hupatz, A.J. Achazi, S. Sobottka, B. Sarkar, B. Paulus, C.A. Schalley— 2017

Donor-acceptor materials with small HOMO-LUMO gaps are important in molecular electronics, but often difficult to synthesise. A simple and efficient way to position tetrathiafulvalene (TTF) as the donor and naphthalene diamide (NDI) as the acceptor in close proximity to each other in a divalent crown/ammonium pseudo[2]rotaxane is presented. The divalent design provides high chelate cooperativity and much stronger binding compared to a monovalent analogue. The pseudo[2]rotaxane is then doubly interlocked by stoppering it in a catalyst-free 1,3-dipolar cycloaddition. UV/Vis and cyclic voltammetry experiments with the resulting [2]rotaxane reveal the optoelectronic properties of the intramolecular charge-transfer with a small HOMO-LUMO energy gap. Redox-switching experiments show the rotaxane to be pentastable. DFT calculations provide insight into the electronic structures of the five redox-states.

Title229
A Divalent Pentastable Redox-Switchable Donor-Acceptor Rotaxane
AuthorH.V. Schröder, H. Hupatz, A.J. Achazi, S. Sobottka, B. Sarkar, B. Paulus, C.A. Schalley
Date20170106
IdentifierDOI: 10.1002/chem.201605710
Source(s)
CitationChem. Eur. J. 2017, 23, 2960-2967
TypeText