Chiral Binaphthalene Building Blocks for Self-Assembled Nanoscale CPL Emitters

Author:

Hsieh Yu-Yu12,Shyue Jing-Jong3,Chao Yu-Chiang4,Wong Ken-Tsung25,Bassani Dario M.1ORCID

Affiliation:

1. Univ. Bordeaux, CNRS, Bordeaux INP, ISM UMR 5255, F-33400 Talence, France

2. Department of Chemistry, National Taiwan University, Taipei 10617, Taiwan

3. Research Center for Applied Sciences, Academia Sinica, Taipei 11529, Taiwan

4. Department of Physics, National Taiwan Normal University, Taipei 11677, Taiwan

5. Institute of Atomic and Molecular Science, Academia Sinica, Taipei 10617, Taiwan

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.

Funder

ANR

MOST

IDEX University of Bordeaux

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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