Bis- and Tris-fused Tetrathiafulvalenes Extended with Anthracene-9,10-diylidene

Daisuke Ogi; Yusuke Fujita; Shigeki Mori; Takashi Shirahata; Yohji Misaki

doi:10.1021/acs.orglett.6b02944

Bis- and Tris-fused Tetrathiafulvalenes Extended with Anthracene-9,10-diylidene

Org Lett. 2016 Nov 18;18(22):5868-5871. doi: 10.1021/acs.orglett.6b02944. Epub 2016 Nov 4.

Authors

Daisuke Ogi¹, Yusuke Fujita¹, Shigeki Mori^{2

3}, Takashi Shirahata^{1

3}, Yohji Misaki^{1

3}

Affiliations

¹ Department of Applied Chemistry, Graduate School of Engineering, Ehime University , 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan.
² Advanced Research Support Center, Ehime University , 2-5 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan.
³ Research Unit for Power Generation and Storage Materials, Ehime University , Matsuyama, Ehime 790-8577, Japan.

PMID: 27934508
DOI: 10.1021/acs.orglett.6b02944

Abstract

Bis- and tris-fused π-electron donors composed of extended tetrathiafulvalene with anthraquinoid spacers (4 and 5) were successfully synthesized. X-ray structure analysis of tetrakis(methylthio)-5 (5a) revealed that the molecule adopted a transoid-cisoid conformation. The cyclic voltammogram of 4a is composed of two pairs of two-electron redox waves, while the cyclic voltammogram of tetrakis(hexylthio) derivative 5b consists of one pair of four-electron redox waves and one pair of two-electron redox waves, respectively. Spectroelectrochemistry of 4a and ¹H NMR spectrum of a 4b salt revealed that two positive charges in 4²⁺ are distributed mainly on one TTFAQ (9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene) moiety.

Publication types

Research Support, Non-U.S. Gov't