Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.orgel.2012.07.015
Title: Isomers of dialkyl diketo-pyrrolo-pyrrole: Electron-deficient units for organic semiconductors
Authors: Zhao, B.
Sun, K.
Xue, F. 
Ouyang, J. 
Keywords: Band gap
Diketo-pyrrolo-pyrrole (DPP)
Electron-deficient unit
Isomer
Organic solar cell
Issue Date: Nov-2012
Citation: Zhao, B., Sun, K., Xue, F., Ouyang, J. (2012-11). Isomers of dialkyl diketo-pyrrolo-pyrrole: Electron-deficient units for organic semiconductors. Organic Electronics: physics, materials, applications 13 (11) : 2516-2524. ScholarBank@NUS Repository. https://doi.org/10.1016/j.orgel.2012.07.015
Abstract: Diketo-pyrrolo-pyrrole (DPP) is an important electron-deficient unit, and the alkylation of DPP can gives rise to good solubility of organic and polymer semiconductors in solvent. In this paper, we report our observations on the isomers of dialkyl DPP. The alkylation of DPP can take place on both the nitrogen and oxygen atoms, leading to the formation of three isomers. The presence of the isomers is evidenced by the nuclear magnetic resonance (NMR) and mass spectra. The yields of the isomers are affected by the experimental conditions, including the reaction temperature, reaction time and solvent. The isomers have different electronic structures and optical properties as revealed by the UV-Vis absorption spectroscopy, fluorescent spectroscopy, cyclic voltammetry and theoretical simulation using Gaussian 03 program with B3LYP/6-31G(d). Small molecules based on the DPP isomers with dialkylation at different sites were synthesized and investigated as donor materials of organic solar cells (OSCs). The photovoltaic performances of OSCs are consistent with the electronic structures of the DPP isomers. © 2012 Elsevier B.V. All rights reserved.
Source Title: Organic Electronics: physics, materials, applications
URI: http://scholarbank.nus.edu.sg/handle/10635/64925
ISSN: 15661199
DOI: 10.1016/j.orgel.2012.07.015
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