Issue 14, 2018

Face-on vs. edge-on: tuning the structure of tetrathiafulvalene monolayers with solvent

Abstract

Tetrathiafulvalene (TTF) is one of the most widely used building blocks for organic conductors and redox-active materials. The ability to control the supramolecular structure of these materials, particularly at interfaces, is critical for application in devices. In this work, we show how the structure of N-alkylated tetrathiafulvalenecarboxyamide TTFAm18 films on graphite can be tuned between the edge-on and face-on orientation, depending on the choice of the solvent. The former orientation is realized in non-polar solvents and results in the formation of 1D π-stacks of TTF moieties that are held together by H-bonding of carboxyamide substituents. The latter orientation is enforced by the use of polar H-bonding solvents (alkanoic acids) which break intermolecular H-bonding and maximize the interaction of TTF molecules with the surface. In both cases, the surface density of TTFs is precisely defined by the length of the alkyl chain. Using Scanning Tunneling Microscopy and Atomic Force Microscopy, we show how the supramolecular assemblies observed at the liquid–solid interface can be transferred to growing dry films, thus paving the way for the application of such periodically structured materials in devices.

Graphical abstract: Face-on vs. edge-on: tuning the structure of tetrathiafulvalene monolayers with solvent

Supplementary files

Article information

Article type
Paper
Submitted
14 des 2017
Accepted
08 feb 2018
First published
08 feb 2018

J. Mater. Chem. C, 2018,6, 3787-3791

Face-on vs. edge-on: tuning the structure of tetrathiafulvalene monolayers with solvent

C. Fu, E. Orgiu and D. F. Perepichka, J. Mater. Chem. C, 2018, 6, 3787 DOI: 10.1039/C7TC05757A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements