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1,1′-Bi(2-naphthol-4,5-dicarboximide)s: blue emissive axially chiral scaffolds with aggregation-enhanced emission properties

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Abstract

1,1′-Binaphthol (BINOL) is a versatile chiral reagent with widespread applications in asymmetric catalysis and fluorescent bio-sensing and imaging. However, unsubstituted BINOLs exhibit only weak and short-wavelength emission, limiting their scope for the latter applications. Herein, we report axially chiral 1,1′-bi(2-naphthol-4,5-dicarboximide)s which show two reversible reductions, bright blue light fluorescence with fluorescence quantum yields up to 0.67, and aggregation-enhanced emission characteristics. Single crystal X-ray analysis revealed an intriguing double helical supramolecular polymer motif formed by π–π stacking interactions between 2-naphthol-4,5-dicarboximide units. The enantiomers of racemic 1,1′-bi(2-naphthol-4,5-dicarboximide)s were resolved on chiral columns and studied by CD spectroscopy.

Graphical abstract: 1,1′-Bi(2-naphthol-4,5-dicarboximide)s: blue emissive axially chiral scaffolds with aggregation-enhanced emission properties

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Publication details

The article was received on 08 Sep 2019, accepted on 07 Oct 2019 and first published on 10 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01090D
Org. Chem. Front., 2019, Advance Article

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    1,1′-Bi(2-naphthol-4,5-dicarboximide)s: blue emissive axially chiral scaffolds with aggregation-enhanced emission properties

    M. Chen, Y. Zhang, M. O. Vysotsky, J. O. Lindner, M. Li, M. Lin and F. Würthner, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01090D

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