학술논문
Symmetrically functionalized diketopyrrolopyrrole with alkylated thiophene moiety: from synthesis to electronic devices applications.
Document Type
Article
Author
Source
Subject
*PYRROLE derivatives
*SEMICONDUCTOR synthesis
*STILLE reaction
*COUPLING reactions (Chemistry)
*CHEMISTRY methodology
*CHEMICAL synthesis
*FRONTIER orbitals
*THIOPHENES
*ALKYL group
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Language
ISSN
0022-2461
Abstract
A symmetrically conjugated molecular semiconductor derived from diketopyrrolopyrrole (DPP), i.e., 2,5-dihexadecyl-3,6-bis(5-(3-hexylthiophen-2-yl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione [ DPP(3HT)2], has been synthesized using the Stille coupling reaction. The optical band gap of DPP(3HT)2 is found to be 1.65 eV with HOMO energy level of −5.13 eV. DPP(3HT)2 is thermally stable up to 348 °C exhibiting only 5 % weight loss. X-ray diffraction analysis revealed the DPP(3HT)2 to be polycrystalline with a high degree of crystallinity. It showed highly narrow and strong diffraction peaks with a d-spacing of ca. 30.18 Å (at 2 θ = 2.09°, full width at half maximum: 2 θ = 0.126°) indicating an end-to-end packing distance with the long alkyl chains (along the a-axis) being slightly tilted and partially interdigitated for effective packing. Field-effect transistors and complementary inverters employing DPP(3HT)2 as a p-channel semiconductor have been fabricated and characterized. Graphical Abstract: [Figure not available: see fulltext.] [ABSTRACT FROM AUTHOR]