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Synfacts 2013; 9(1): 0045
DOI: 10.1055/s-0032-1317885
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Electron-Acceptor Pentacene Derivative

Contributor(s):
Timothy M. Swager
,
Silvia V. Rocha
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
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Publication History

Publication Date:
17 December 2012 (online)

 
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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.


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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.


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