Multicolor emission based on a N, N'-Disubstituted dihydrodibenzo [a, c] phenazine crown ether macrocycle

Chang-Shun Ma; Chengyuan Yu; Cai-Xin Zhao; Shang-Wu Zhou; Ruirui Gu

doi:10.3389/fchem.2022.1087610

Multicolor emission based on a N, N'-Disubstituted dihydrodibenzo [a, c] phenazine crown ether macrocycle

Front Chem. 2022 Dec 5:10:1087610. doi: 10.3389/fchem.2022.1087610. eCollection 2022.

Authors

Chang-Shun Ma¹, Chengyuan Yu¹, Cai-Xin Zhao¹, Shang-Wu Zhou¹, Ruirui Gu¹

Affiliation

¹ Key Laboratory for Advanced Materials, Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, Institute of Fine Chemicals, East China University of Science and Technology, Shanghai, China.

Abstract

Dynamic fluorophore 9,14-diphenyl-9,14-dihydrodibenzo[a,c]phenazine (DPAC) affords a new platform to produce diverse emission outputs. In this paper, a novel DPAC-containing crown ether macrocycle D-6 is synthesized and characterized. Host-guest interactions of D-6 with different ammonium guests produced a variety of fluorescence with hypsochromic shifts up to 130 nm, which are found to be affected by choice of solvent or guest and host/guest stoichiometry. Formation of supramolecular complexes were confirmed by UV-vis titration, ¹H NMR and HRMS spectroscopy.

Keywords: conformational adaptivity; host-guest interactions; multicolor emission; supramolecular chemistry; vibration-induced emission.