BODIPY-Based Antiaromatic Macrocycles: Facile Synthesis by Knoevenagel Condensation and Unusual Aggregation-Enhanced Two-Photon Absorption Properties

Ming Hui Chua, Taeyeon Kim, Zheng Long Lim, Tullimilli Y. Gopalakrishna, Yong Ni, Jianwei Xu, Dongho Kim, Jishan Wu

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Two stable boron dipyrromethene (BODIPY)-based antiaromatic macrocycles, Mc-Fur and Mc-Th, were synthesized through a one-pot Knoevenagel condensation reaction between a BODIPY precursor and furan-2,5-dicarboxaldehyde or thiophene-2,5-dicarboxaldehyde, respectively. 1H NMR spectroscopic characterization of the two macrocycles supported their highly antiaromatic character. The oxidation properties of the two macrocycles were studied through electron spin resonance spectroscopy and UV/Vis absorption spectrophotometry, which suggested the formation of a stable monoradical cation species on first oxidation followed by an aromatic dicationic species on subsequent oxidation. Both molecules have a nearly planar π-conjugated backbone and show a strong tendency to aggregate in solution due to efficient stacking of the antiaromatic macrocycles. Transient absorption and two-photon absorption (TPA) measurements in solution and aggregated states of the macrocycles revealed that aggregation resulted in large enhancement of TPA cross sections and increased excited-state lifetimes, in accordance with the decrease in the antiaromatic character in the aggregated state.

Original languageEnglish
Pages (from-to)2232-2241
Number of pages10
JournalChemistry - A European Journal
Issue number9
Publication statusPublished - 2018 Feb 9


All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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