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Synfacts 2008(3): 0253-0253  
DOI: 10.1055/s-2008-1042717
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Functionalized Naphthalene Diimides

Contributor(s): Timothy M. Swager, Trisha L. Andrew
H. Krüger*, S. Janietz, D. Sainova, D. Dobreva, N. Koch, A. Vollmer
Fraunhofer Institute Applied Polymer Research, Potsdam, Humboldt-Universität zu Berlin and Berliner Elekronenspeicherring-Gesellschaft für Synchrotonstrahlung, Germany
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Publication History

Publication Date:
21 February 2008 (online)

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Significance

Tetrabrominated naphthalene di­anhydride was efficiently functionalized with four thiophene rings to yield compound 1, which is soluble in organic solvents unlike its precursors. Following imidation, the four thiophene arms were synthetically extended by iterating bromination and Stille-coupling steps to yield compound 3 in 32% yield. Both compounds 2 and 3 displayed long-wavelength absorption maxima (514 nm and 664 nm, respectively) due to the donor-acceptor interaction between the thiophene (donor) and naphthalene diimide (acceptor) moieties. Field-effect-transistor (FET) devices containing either 2 or 3 showed satisfactory performance under both p-channel and n-channel operation.