Double Lactonization in Triarylamine-Conjugated Dimethyl Diethynylfumarate: Formation of Intensely Colored and Luminescent Quadrupolar Molecules Including a Missing Structural Isomer of Pechmann Dyes

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.