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 | |
| Publication status | Published - Jan 2019 |
| Externally published | Yes |
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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 journal › Article › Research › peer-review
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
VL - 160
SP - 692
EP - 699
JO - Dyes and Pigments
JF - Dyes and Pigments
SN - 0143-7208
ER -