Synthesis and cofacial pi-stacked packing arrangement of 6,13-bis(alkylthio)pentacene

Kenji Kobayashi; Reishi Shimaoka; Masatoshi Kawahata; Masamichi Yamanaka; Kentaro Yamaguchi

doi:10.1021/ol060679x

Synthesis and cofacial pi-stacked packing arrangement of 6,13-bis(alkylthio)pentacene

Org Lett. 2006 May 25;8(11):2385-8. doi: 10.1021/ol060679x.

Authors

Kenji Kobayashi¹, Reishi Shimaoka, Masatoshi Kawahata, Masamichi Yamanaka, Kentaro Yamaguchi

Affiliation

¹ Department of Chemistry, Faculty of Science, Shizuoka University, Suruga-ku, Japan. skkobay@ipc.shizuoka.ac.jp

PMID: 16706532
DOI: 10.1021/ol060679x

Abstract

[reaction: see text] 6,13-Bis(alkylthio)pentacenes directed toward organic field-effect transistors (OFETs) were synthesized by the ZnI(2)-mediated reaction of trans-6,13-dihydroxy-6,13-dihydropentacene with alkylthiols, followed by the dehydrogenative aromatization of the resulting trans-6,13-bis(alkylthio)-6,13-dihydropentacenes with p-chloranil. The X-ray crystallographic analysis of 6,13-bis(methylthio)pentacene reveals that this compound is arranged as a result of cofacial pi-stacking with S-S and S-pi interactions.