1,1′-Bi(2-naphthol-4,5-dicarboximide)s: blue emissive axially chiral scaffolds with aggregation-enhanced emission properties
Literature Information
Publication Date
2019-10-10
DOI
10.1039/C9QO01090D
Impact Factor
5.281
Authors
Meng-Ting Chen, Yang Zhang, Myroslav O. Vysotsky, Joachim O. Lindner, Meng-Hua Li, Mei-Jin Lin, Frank Würthner
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
4,4,5,5-Tetramethyl-2-(1-propyn-1-YL)-1,3,2-dioxaborolane
CAS Number:
347389-75-7
Molecular Formula:
C9H15BO2
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