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Chiral Binaphthalene Building Blocks for Self-Assembled Nanoscale CPL Emitters

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The introduction of biuret hydrogen-bonding sites onto chiral binaphthalene-based chromophores was investigated as a route to sub-micron-sized, vesicle-like aggregates endowed with chiroptical properties. The synthesis was conducted from the corresponding… Click to show full abstract

The introduction of biuret hydrogen-bonding sites onto chiral binaphthalene-based chromophores was investigated as a route to sub-micron-sized, vesicle-like aggregates endowed with chiroptical properties. The synthesis was conducted from the corresponding chiral 4,4′-dibromo-1,1′-bis(2-naphthol) via Suzuki–Miyaura coupling to afford luminescent chromophores whose emission spectrum could be tuned from blue to yellow-green through extension of the conjugation. For all compounds, the spontaneous formation of hollow spheres with a diameter of ca. 200–800 nm was evidenced by scanning electron microscopy, along with strong asymmetry in the circularly polarized absorption spectra. For some compounds, the emission also displayed circular polarization with values of glum = ca. 10–3 which could be increased upon aggregation.

Keywords: chiral binaphthalene; blocks self; binaphthalene building; binaphthalene; self assembled; building blocks

Journal Title: Molecules
Year Published: 2023

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