Issue 11, 2021

Selective formation of spiroborate-based double-stranded hetero-helicates assisted by donor–acceptor interactions

Abstract

Novel ortho-linked tetraphenol strands with electron-deficient naphthalene (NDI) and perylene (PDI) diimide linkers in the middle formed double-stranded homo-helicates bridged by spiroborate groups in the presence of NaBH4. The reaction of an electron-rich porphyrin-linked tetraphenol strand with the NDI-strand quantitatively afforded the double-stranded hetero-helicate assisted by donor–acceptor interactions between the porphyrin and NDI units with a similar molecular length to each other, while that with the longer PDI strand gave a mixture of the corresponding homo- and hetero-helicates. The two isolated homo- and hetero-helicates were successfully resolved into enantiomers by chiral HPLC.

Graphical abstract: Selective formation of spiroborate-based double-stranded hetero-helicates assisted by donor–acceptor interactions

Supplementary files

Article information

Article type
Research Article
Submitted
18 Nah 2021
Accepted
17 Cig 2021
First published
26 Cig 2021

Org. Chem. Front., 2021,8, 2551-2555

Selective formation of spiroborate-based double-stranded hetero-helicates assisted by donor–acceptor interactions

D. Taura, X. Wang, M. Ito and E. Yashima, Org. Chem. Front., 2021, 8, 2551 DOI: 10.1039/D1QO00286D

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