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Synthesis, solvent-dependent emission and two-photon absorption of a triangular –[D–π–A]3– macrocycle

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Abstract

A large triangular arylene–ethynylene macrocycle featuring unique circularly arranged –[D–π–A]3– electronic characteristics is designed and synthesized. The shape-persistent π-conjugated backbone is composed of alternating electron-rich dialkoxyphenanthrene and electron-deficient dicyanodibenzo[f,h]quinoxaline units, connected by ethynylene linkers. The synthesis of such a special macrocyclic molecule is realized by employing a post-cyclization functional group installation strategy. The absorption and emission spectra of the macrocycle are found sensitively dependent on the solvent polarity. By virtue of a conjugated π-scaffold and a cyclic –[D–π–A]3– motif, evident two-photon absorption (2PA) and two-photon excitation fluorescence properties are exhibited, with a 2PA cross section maximum of 3 × 103 GM determined by the Z-scan method.

Graphical abstract: Synthesis, solvent-dependent emission and two-photon absorption of a triangular –[D–π–A]3– macrocycle

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Publication details

The article was received on 23 Dec 2016, accepted on 08 Feb 2017 and first published on 09 Feb 2017


Article type: Research Article
DOI: 10.1039/C6QO00845C
Citation: Org. Chem. Front., 2017, Advance Article
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    Synthesis, solvent-dependent emission and two-photon absorption of a triangular –[D–π–A]3– macrocycle

    T. Li, D. Zhang, R. Wang, Y. Fan, X. Guo, S. Liu, Y. Ma and D. Zhao, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C6QO00845C

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