Subscribe to RSS
DOI: 10.1055/s-2008-1042717
Functionalized Naphthalene Diimides
Contributor(s):Timothy M. Swager, Trisha L. AndrewFraunhofer Institute Applied Polymer Research, Potsdam, Humboldt-Universität zu Berlin and Berliner Elekronenspeicherring-Gesellschaft für Synchrotonstrahlung, Germany
Hybrid Supramolecular Naphthalene Diimide-thiophene Structures and Their Application in Polymer Electronics
Adv. Funct. Mater. 2007, 17: 3715-3723
Publication History
Publication Date:
21 February 2008 (online)
Key words
naphthalene diimides - field-effect transistors - donor-acceptor interactions
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.
Comment
Naphthalene diimides are highly electron-deficient molecules and therefore act as excellent electron acceptors. Compounds 1 and 2 are interesting because, although the four thiophene moieties are non-coplanar with the naphthalene core, a significant red shift (ca. 200 nm) in the absorption maximum is observed relative to the unfunctionalized dianhydride. Moreover, although compound 2 seems perfectly suited for electrochemical polymerization, its irreversible electrochemistry under oxidative conditions precludes the possibility of clean electropolymerization.