Precise control of chirality transfer by adjusting the alkyl substituents of guests

Tingting Hu, Taotao Liu, Zhihao Zhang, Yong Wang, Yonggang Yang, David James Young, Chuanjiang Hu, Jian Ping Lang

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Chirality transfer has been investigated with an m-phthalic diamide-linked zinc bisporphyrinate as host and chiral monoalcohols with different alkyl substituents as guests. The substituent of the guest alcohol had a significant effect on chirality transfer. An increase in the number of carbon atoms from one to three resulted in circular dichroism (CD) sign inversion for the corresponding host-guest complexes. The crystal structures of these zinc bisporphyrinate-monoalcohol complexes revealed two types of orientation for the phenyl ring of the guests: one with the phenyl ring facing the porphyrin plane, and the other with the phenyl ring towards the linker. The chirality transfer mechanism was further studied by DFT and revealed that adjusting the chain length of the alkyl substituent could control the steric interaction between the alkyl group and the porphyrin plane, resulting in different chirality transfer outcomes.

Original languageEnglish
Pages (from-to)692-699
Number of pages8
JournalDyes and Pigments
Volume160
DOIs
Publication statusPublished - Jan 2019
Externally publishedYes

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Chirality
Porphyrins
Zinc
Diamide
Dichroism
Chain length
Discrete Fourier transforms
Alcohols
Carbon
Crystal structure
Atoms

Cite this

Hu, Tingting ; Liu, Taotao ; Zhang, Zhihao ; Wang, Yong ; Yang, Yonggang ; Young, David James ; Hu, Chuanjiang ; Lang, Jian Ping. / Precise control of chirality transfer by adjusting the alkyl substituents of guests. In: Dyes and Pigments. 2019 ; Vol. 160. pp. 692-699.
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abstract = "Chirality transfer has been investigated with an m-phthalic diamide-linked zinc bisporphyrinate as host and chiral monoalcohols with different alkyl substituents as guests. The substituent of the guest alcohol had a significant effect on chirality transfer. An increase in the number of carbon atoms from one to three resulted in circular dichroism (CD) sign inversion for the corresponding host-guest complexes. The crystal structures of these zinc bisporphyrinate-monoalcohol complexes revealed two types of orientation for the phenyl ring of the guests: one with the phenyl ring facing the porphyrin plane, and the other with the phenyl ring towards the linker. The chirality transfer mechanism was further studied by DFT and revealed that adjusting the chain length of the alkyl substituent could control the steric interaction between the alkyl group and the porphyrin plane, resulting in different chirality transfer outcomes.",
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Precise control of chirality transfer by adjusting the alkyl substituents of guests. / Hu, Tingting; Liu, Taotao; Zhang, Zhihao; Wang, Yong; Yang, Yonggang; Young, David James; Hu, Chuanjiang; Lang, Jian Ping.

In: Dyes and Pigments, Vol. 160, 01.2019, p. 692-699.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Zhang, Zhihao

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AU - Hu, Chuanjiang

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AB - Chirality transfer has been investigated with an m-phthalic diamide-linked zinc bisporphyrinate as host and chiral monoalcohols with different alkyl substituents as guests. The substituent of the guest alcohol had a significant effect on chirality transfer. An increase in the number of carbon atoms from one to three resulted in circular dichroism (CD) sign inversion for the corresponding host-guest complexes. The crystal structures of these zinc bisporphyrinate-monoalcohol complexes revealed two types of orientation for the phenyl ring of the guests: one with the phenyl ring facing the porphyrin plane, and the other with the phenyl ring towards the linker. The chirality transfer mechanism was further studied by DFT and revealed that adjusting the chain length of the alkyl substituent could control the steric interaction between the alkyl group and the porphyrin plane, resulting in different chirality transfer outcomes.

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