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Nitrogen-doped star-shaped polycyclic aromatic hydrocarbons based on fused triazatruxenes: synthesis and optoelectronic properties

Abstract

A new class of nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs) based on naphthalene-fused triazatruxenes, named as TATNaCn (n = 1-3), were successfully designed, synthesized and characterized. During the oxidative cyclodehydrogenation, multiple dehydrocyclization molecules can be effectively separated apart in a single reaction, implying a stepwise ring-closed process. A combination of thermal, optical, and electrochemical characterization of these stepwise ring-closed N-PAHs was conducted to explore the influence of the ring fused process on the optoelectronic characteristics of N-PAHs. The absorption bands of the fused products TATNaCn are red-shifted compared to those of the TATNa precursor both in dilute solution and thin solid films, suggesting enlarged π-conjugation induced by the fused rings. Furthermore, the band-gap energies of these N-PAHs are facilely modulated with varying the number of closed rings, leading to tunable emission characteristics. The way of introducting triazatruxenes to construct N-PAHs provides a general guideline for exploring novel heteroatom-doped PAHs with facilely tunable optoelectronic properties.

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Publication details

The article was received on 17 Jul 2017, accepted on 07 Oct 2017 and first published on 09 Oct 2017


Article type: Paper
DOI: 10.1039/C7NJ02597A
Citation: New J. Chem., 2017, Accepted Manuscript
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    Nitrogen-doped star-shaped polycyclic aromatic hydrocarbons based on fused triazatruxenes: synthesis and optoelectronic properties

    C. Liu, C. Cheng, Y. Jiang, W. Lai and W. Huang, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ02597A

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