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

Citation:

Li, T. ; Zhang, D. ; Wang, R. ; Fan, Y. ; Guo, X. ; Liu, S. ; Ma, Y. *; Zhao, D. *. Synthesis, Solvent-Dependent Emission and Two- Photon Absorption of a Triangular -[D-Π-A]3- Macrocycle. Org. Chem. Front. 2017, 4, 737-742.

摘要:

A large triangular arylene-ethynylene macrocycle featuring unique circularly arranged -[D-pi-A](3)- electronic characteristics is designed and synthesized. The shape-persistent pi-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 pi-scaffold and a cyclic -[D-pi-A](3)- motif, evident two-photon absorption (2PA) and two-photon excitation fluorescence properties are exhibited, with a 2PA cross section maximum of 3 x 10(3) GM determined by the Z-scan method.

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See also: 2017