Issue 50, 2017

A facile approach toward 1,2-diazabenzo[ghi]perylene derivatives: structures and electronic properties

Abstract

A new class of pyridazine fused aromatics, 1,2-diazabenzo[ghi]perylenes, is conveniently synthesized from 2,7-dihydroxynaphthalene via intermolecular oxidative coupling followed by a condensation reaction. These new compounds are fully characterized via X-ray crystallographic analysis, optical spectroscopy and electrochemistry, in addition to DFT calculations. They show a twisted structure and unique P-/P- and M-/M-enantiomer pairs are observed in their single crystals. They exhibit intramolecular charge transfer character and emit at a longer wavelength with a larger Stokes shift compared with their all-carbon analog.

Graphical abstract: A facile approach toward 1,2-diazabenzo[ghi]perylene derivatives: structures and electronic properties

Supplementary files

Article information

Article type
Communication
Submitted
01 May 2017
Accepted
25 May 2017
First published
25 May 2017

Chem. Commun., 2017,53, 6740-6743

A facile approach toward 1,2-diazabenzo[ghi]perylene derivatives: structures and electronic properties

H. Wei, T. Qiu, X. Huang, J. Zhou, J. Guo, C. Jiang, S. Luo, Z. Zeng and J. Wu, Chem. Commun., 2017, 53, 6740 DOI: 10.1039/C7CC03362A

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