Synthesis, Characterization, and Chiroptical Properties of [6]Helicene-Containing Nanographenes from the Modification of Axially Chiral Arenes.

Two π-extended [6]helicenes 7 and 10a have been successfully synthesized through the modification of their corresponding axially chiral precursors, which were verified by single crystal X-ray diffraction analysis. The (P)- and (M)-enantiomers of compounds 7 and 10a were resolved via chiral high-performance liquid chromatography (HPLC). However, the enantiomers of the axially chiral arenes 2, 3, and 4 could not be resolved by chiral HPLC due to their susceptibility to racemization at room temperature. The as-prepared arenes were characterized using UV-vis absorption and fluorescence spectroscopy, cyclic voltammetry, circular dichroism (CD) spectroscopy, and circularly polarized luminescence (CPL) spectroscopy. The CD and CPL spectra of 7 and 10a exhibit opposite Cotton effect and fluorescence signals, rendering them promising ingredients for CPL emitters.

• Publication year

  2025

• Venue

  Journal of Organic Chemistry

• Publication date

  2025-08-05

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.joc.5c01154PMID 40763216
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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