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Issue 12, 2014
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Electron deficient diketopyrrolopyrrole dyes for organic electronics: synthesis by direct arylation, optoelectronic characterization, and charge carrier mobility

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Abstract

Four electron deficient small molecules based on the diketopyrrolopyrrole (DPP) chromophore were synthesized using microwave-assisted direct arylation reactivity. These molecules are based upon an acceptor–donor–acceptor–donor–acceptor (A1–D–A2–D–A1) framework, where DPP is utilized as the central acceptor (A2) unit. We compared the effect of naphthalimide vs. phthalimide terminal acceptors (A1), and different DPP (A2) alkyl groups, on the optical, thermal, electrochemical and electronic properties. A combination of absorption and emission spectroscopy, differential scanning calorimetry, thermal gravimetric analysis, cyclic voltammetry, ultraviolet photoelectron spectroscopy, charge carrier mobility, and DFT calculations were used to characterize the four materials. All compounds were found to have narrow band-gaps, deep HOMO/LUMO levels, and were able to effectively act as electron transport materials.

Graphical abstract: Electron deficient diketopyrrolopyrrole dyes for organic electronics: synthesis by direct arylation, optoelectronic characterization, and charge carrier mobility

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Supplementary files

Article information


Submitted
30 Oct 2013
Accepted
22 Jan 2014
First published
24 Jan 2014

J. Mater. Chem. A, 2014,2, 4198-4207
Article type
Paper
Author version available

Electron deficient diketopyrrolopyrrole dyes for organic electronics: synthesis by direct arylation, optoelectronic characterization, and charge carrier mobility

A. D. Hendsbee, J. Sun, L. R. Rutledge, I. G. Hill and G. C. Welch, J. Mater. Chem. A, 2014, 2, 4198
DOI: 10.1039/C3TA14414C

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