A tetrathiafulvalene-functionalized naphthalene diimide: synthesis, electrochemical and photophysical properties

Jaggi, Michael; Schmid, Belinda; Liu, Shi-Xia; Bhosale, Sheshanath V.; Rivadehi, Shadi; Langford, Steven J.; Decurtins, Silvio (2011). A tetrathiafulvalene-functionalized naphthalene diimide: synthesis, electrochemical and photophysical properties. Tetrahedron, 67(38), pp. 7231-7235. Kidlington, UK: Elsevier Science 10.1016/j.tet.2011.07.069

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A tetrathiafulvalene donor has been attached to the naphthalene diimide core via a rigid bridge affording a new planar molecular dyad. Its electronic properties have been studied experimentally by the combination of electrochemistry and UV-vis-NIR spectroscopy. Various electronic excited charge-transfer states are generated in different oxidation states, leading to almost full absorption in the visible to near-IR region with high extinction coefficients. The observed electronic properties are explained on the basis of density-functional-theory. In particular, the oxidized radical species show a strong tendency to undergo aggregation, in which the long-distance attractive interactions overcome the electrostatic repulsions. (C) 2011 Elsevier Ltd. All rights reserved.

Item Type:

Journal Article (Original Article)


08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)

UniBE Contributor:

Liu, Shi-Xia, Decurtins, Silvio




Elsevier Science




Factscience Import

Date Deposited:

04 Oct 2013 14:26

Last Modified:

05 Dec 2022 14:08

Publisher DOI:


Web of Science ID:



https://boris.unibe.ch/id/eprint/9572 (FactScience: 215329)

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