Lie J, Xiong Y, Wu Q, Wang S, Gao X, Li H * Shanghai Institute of Organic Chemistry,
P. R. of China
Synthesis and Physicochemical Properties of Strong Electron Acceptor 14,14,15,15-Tetracyano-6,13-pentacenequinodimethane
(TCPQ) Diimide.
Eur. J. Org. Chem. 2012; 6136-6139
Key words
pentacenes - cycloaddition - tetracyanoquino-dimethanes
Significance
This paper reports the synthesis of an extended tetracyanoquinodimethane (TCNQ) analogue,
1. Although this is not the first report of a TCNQ-like acene, the method reported
by the authors consists of only six steps, including a double Diels–Alder reaction
and a Knoevenagel condensation as key steps. The presence of the diimide substituents
not only increases the solubility of the final molecule, but also has implications
on its electronic properties.
Comment
Electron-acceptor molecules are essential in organic electronic materials, and an
important property of such molecules is the LUMO energy level. The authors report
a LUMO level of
–4.03 eV for 1, which makes this molecule and derivatives of it, good candidates for a variety
of applications.
