Synthesis, solvent-dependent emission and two-photon absorption of a triangular –[D–π–A]3– macrocycle. Issue 5 (21st February 2017)

• Record Type: Journal Article
• Authors: Li, Tian; Zhang, Di; Wang, Ranran; Fan, Yuanpeng; Guo, Xinyan; Liu, Shuai; Ma, Yuguo; Zhao, Dahui
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 5(2017)
• Page Start: 737
• Page End: 742
• Publication Date: 2017-02-21
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c6qo00845c
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A large π–conjugated macrocycle featuring a –[D–π–A]3 – backbone is synthesized, exhibiting strongly solvent-dependent fluorescence and evident two-photon absorption ability. 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 × 10 3 GM determined by the Z -scan method.