Double lactonization in triarylamine-conjugated dimethyl diethynylfumarate: formation of intensely colored and luminescent quadrupolar molecules including a missing structural isomer of Pechmann dyes

Mikihiro Hayashi; Fumiyuki Toshimitsu; Ryota Sakamoto; Hiroshi Nishihara

doi:10.1021/ja2054176

Double lactonization in triarylamine-conjugated dimethyl diethynylfumarate: formation of intensely colored and luminescent quadrupolar molecules including a missing structural isomer of Pechmann dyes

J Am Chem Soc. 2011 Sep 21;133(37):14518-21. doi: 10.1021/ja2054176. Epub 2011 Aug 25.

Authors

Mikihiro Hayashi¹, Fumiyuki Toshimitsu, Ryota Sakamoto, Hiroshi Nishihara

Affiliation

¹ Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 21842858
DOI: 10.1021/ja2054176

Abstract

Acid-induced double lactonization in triarylamine-conjugated dimethyl diethynylfumarate E-1 opens up a new synthetic route to Pechmann dyes. This one-pot reaction affords three donor-acceptor-donor quadrupolar molecules (P(55)-1, P(66)-1, and P(56)-1); P(56)-1 comprises a missing structural isomer of Pechmann dyes. They are intensely colored and brightly luminescent. An organic field-effect transistor device fabricated with P(66)-1 functions as a p-type semiconductor.