title: Hydroquinone-pyrrole dyads with varied linkers.
abstract: A series of pyrroles functionalized in the 3-position with p-dimethoxybenzene via various linkers (CH2, CH2CH2, CH=CH, C≡C) has been synthesized. Their electronic properties have been deduced from (1)H NMR, (13)C NMR, and UV-vis spectra to detect possible interactions between the two aromatic subunits. The extent of conjugation between the subunits is largely controlled by the nature of the linker, with the largest conjugation found with the trans-ethene linker and the weakest with the aliphatic linkers. DFT calculations revealed substantial changes in the HOMO-LUMO gap that correlated with the extent of conjugation found experimentally. The results of this work are expected to open up for use of the investigated compounds as components of redox-active materials in sustainable, organic electrical energy storage devices.
authors.affiliation: Nanotechnology and Functional Materials, Department of Engineering Sciences, The Ångström Laboratory, Uppsala University, Box 534, SE-751 21 Uppsala, Sweden.
authors.forename: Hao
authors.initials: H
authors.lastname: Huang
authors.affiliation: Nanotechnology and Functional Materials, Department of Engineering Sciences, The Ångström Laboratory, Uppsala University, Box 534, SE-751 21 Uppsala, Sweden.
authors.forename: Christoffer
authors.initials: C
authors.lastname: Karlsson
authors.affiliation: Nanotechnology and Functional Materials, Department of Engineering Sciences, The Ångström Laboratory, Uppsala University, Box 534, SE-751 21 Uppsala, Sweden.
authors.forename: Maria
authors.initials: M
authors.lastname: Strømme
authors.affiliation: Nanotechnology and Functional Materials, Department of Engineering Sciences, The Ångström Laboratory, Uppsala University, Box 534, SE-751 21 Uppsala, Sweden.
authors.forename: Martin
authors.initials: M
authors.lastname: Sjödin
authors.affiliation: Department of Chemistry - BMC, Biomedical Centre, Uppsala University, Box 576, SE-751 23 Uppsala, Sweden.
authors.forename: Adolf
authors.initials: A
authors.lastname: Gogoll
keywords: conjugation; heterocycles; hydroquinone; linker effect; pyrrole