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

doi:10.1016/j.dyepig.2018.09.004

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 journal › Article › peer-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 language	English
Pages (from-to)	692-699
Number of pages	8
Journal	Dyes and Pigments
Volume	160
DOIs	https://doi.org/10.1016/j.dyepig.2018.09.004
Publication status	Published - Jan 2019
Externally published	Yes

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10.1016/j.dyepig.2018.09.004

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title = "Precise control of chirality transfer by adjusting the alkyl substituents of guests",

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.",

keywords = "Chirality transfer, Circular dichroism, Porphyrin",

author = "Tingting Hu and Taotao Liu and Zhihao Zhang and Yong Wang and Yonggang Yang and Young, {David James} and Chuanjiang Hu and Lang, {Jian Ping}",

year = "2019",

month = jan,

doi = "10.1016/j.dyepig.2018.09.004",

language = "English",

volume = "160",

pages = "692--699",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier",

}

TY - JOUR

T1 - Precise control of chirality transfer by adjusting the alkyl substituents of guests

AU - Hu, Tingting

AU - Liu, Taotao

AU - Zhang, Zhihao

AU - Wang, Yong

AU - Yang, Yonggang

AU - Young, David James

AU - Hu, Chuanjiang

AU - Lang, Jian Ping

PY - 2019/1

Y1 - 2019/1

N2 - 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.

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.

KW - Chirality transfer

KW - Circular dichroism

KW - Porphyrin

UR - http://www.scopus.com/inward/record.url?scp=85053051030&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2018.09.004

DO - 10.1016/j.dyepig.2018.09.004

M3 - Article

AN - SCOPUS:85053051030

VL - 160

SP - 692

EP - 699

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

ER -

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

Abstract

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