Stoichiometrically controlled chirality inversion in zinc bisporphyrinate-monoamine complexes

Tingting Hu, Chuanjiang Hu, Yong Wang, David James Young, Jian Ping Lang

Research output: Contribution to journalArticle

Abstract

We have designed and synthesized a novel amide-linked bisporphyrin with a 2-naphthalenecarboxamide substituent on the linker. The chirality sensing ability of this zinc porphyrinate towards chiral monoamines has been examined. Circular dichroism studies indicate chirality transfer from chiral monoamines to the corresponding host-guest complexes. Interestingly, when optically pure 1-(1-naphthyl)ethylamine is used as a guest, stoichiometrically controlled chirality inversion occurs in the formation of the corresponding zinc bisporphyrinate-monoamine complexes. Both CD and NMR spectra indicate that 1:1 and 1:2 complexes are formed in solution. DFT calculations suggest that steric interactions between the substituent of the linker and the guest in the 1:2 complex are responsible for this unprecedented observation. Our studies provide a unique bisporphyrin system for demonstrating that chirality transfer to the host can be tuned by changing the substituent of the linker.

Original languageEnglish
Pages (from-to)5503-5512
Number of pages10
JournalDalton Transactions
Volume47
Issue number15
DOIs
Publication statusPublished - 21 Apr 2018
Externally publishedYes

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