Electron Push-Pull Effects in 3,9-Bis(p-(R)-diphenylamino)perylene and Constraint on Emission Color Tuning.

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ID: 27381
2019
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Abstract
A series of perylene-based donor-acceptor-donor (D-A-D) compounds, 3,9-Bis(p-(R)-diphenylamino)perylene (R: CN (2a), F (2b), H (2c), Me (2d), and OMe (2e)), were synthesized using 3,9-dibromoperylene with p-(R)-diphenylamine, and the intramolecular charge transfer (ICT) on the D-A-D system with regards to the electron push-pull substituents effect was investigated. By introducing various p-(R)-diphenylamine derivatives with electron-donating or electron-withdrawing R groups, the energy band gaps of the D-A-D compounds were systematically controlled, and the emission colors were efficiently tuned from green to red. As expected, the steady state emission spectra of all D-A-D compounds were observed, as well as the emission color being controlled, depending on the Hammett substituent constants (σp). In the Lippert-Mataga plots, the different charge transfer character was observed depending on the electron push-pull substitution, which showed gradually increased ICT characters from the electron-withdrawing to donating substitution. However, exceptionally, the strong electron withdrawing group of CN substituted 2a did not correlate with the other R group compounds. From the experimental data and DFT calculations, we assume that there is a constraint on emission color tuning to make higher energy of blue emission in the D-A-D molecular system, due to the reverse charge transfer property caused by the strong electron withdrawing group.
Reference Key
ahn2019electronthe Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Ahn, Mina;Kim, Min-Ji;Wee, Kyung-Ryang;
Journal The Journal of organic chemistry
Year 2019
DOI
10.1021/acs.joc.9b01849
URL
Keywords Keywords not found

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