Naphtho[1,2-b:5,6-b′]dithiophene Building Blocks and their Complexation with Cyclobis(paraquat-p-phenylene)

Morten Jensen, Gunnar Olsen, Rikke Kristensen, Kazuo Takimiya, Jan O. Jeppesen*

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The synthesis and characterization of 2,7-bis(hydroxymethyl)naphtho[1,2-b:5,6-b′]dithiophene 1 is described. Electrochemical investigations revealed that 1 and its precursor naphtho[1,2-b:5,6-b′]dithiophene (NDT) are moderate π-electron donors. It was found that both compounds can form 1:1 complexes with the π-electron accepting cyclophane cyclobis(paraquat-p-phenylene) (CBPQT4+). UV/Vis spectroscopy was used to determine the binding constants (Ka) associated with the complexation process leading to the formation of the [2]pseudorotaxanes and the superstructures were characterized using 1H NMR spectroscopy and molecular modelling. The results show that the Ka value for 1⊂CBPQT4+ is approximately seven times larger as compared to NDT⊂CBPQT4+, which can be ascribed to the fact that 1 is a better π-electron donor compared to the parent NDT and therefore is capable of forming stronger charge transfer (CT) interactions with CBPQT4+. The strong π-electron donor tetrathiafulvalene (TTF) was used to carry out switching studies between the [2]pseudorotaxanes NDT⊂CBPQT4+ and TTF⊂CBPQT4+ and the results suggest that NDT derivatives in combination with TTF appear as promising building blocks for the development of new electroactive molecular machines based on CBPQT4+.

TidsskriftEuropean Journal of Organic Chemistry
Udgave nummer46
Sider (fra-til)7532-7540
StatusUdgivet - 15. dec. 2019

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