Issue 5, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
23 12 2016
Accepted
08 2 2017
First published
09 2 2017

Org. Chem. Front., 2017,4, 737-742

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, 4, 737 DOI: 10.1039/C6QO00845C

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