Issue 12, 2017

Synthesis of perfluoroalkylated pentacenes and evaluation of their fundamental physical properties

Abstract

Symmetrical and unsymmetrical pentacenes carrying two perfluoroalkyl (Rf) chains, at the 6 and 13 positions, were synthesized from easily available pentacene-6,13-quinone via facile three or four step reactions. After extensive evaluation, it was clearly found that the control of both the electron density of the aromatic rings on the pentacene core and molecular alignment in the crystalline state nicely affected their physical properties. Thus, we successfully prove in this article that (1) their anti-oxidation ability was significantly enhanced due to a decrease in the HOMO and LUMO energy and (2) a distinct difference in charge-transporting properties was observed between the symmetrical and unsymmetrical pentacenes.

Graphical abstract: Synthesis of perfluoroalkylated pentacenes and evaluation of their fundamental physical properties

Supplementary files

Article information

Article type
Paper
Submitted
07 Jan 2017
Accepted
03 Feb 2017
First published
15 Feb 2017

Org. Biomol. Chem., 2017,15, 2522-2535

Synthesis of perfluoroalkylated pentacenes and evaluation of their fundamental physical properties

S. Yamada, K. Kinoshita, S. Iwama, T. Yamazaki, T. Kubota, T. Yajima, K. Yamamoto and S. Tahara, Org. Biomol. Chem., 2017, 15, 2522 DOI: 10.1039/C7OB00043J

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