Critical Role of Achiral Guest Molecules in Planar Chirality Inversion of Alanine-Appended Pillar[5]arenes

被引：32

作者：

Park, Jaehyeon ^{[1
,2
]}

Choi, Yeonweon ^{[3
]}

Lee, Shim Sung ^{[1
,2
]}

Jung, Jong Hwa ^{[1
,2
]}

机构：

[1] Gyeongsang Natl Univ, Dept Chem, Jinju 52828, South Korea

[2] Gyeongsang Natl Univ, Res Inst Nat Sci, Jinju 52828, South Korea

[3] Natl Inst Chem Safety, Accid Prevent & Assessment Div 2, Daejeon 34111, South Korea

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 04期

关键词：

DIASTEREOSELECTIVE SYNTHESIS; SELF-ASSEMBLES; COMPLEXATION; HOST; CYCLOADDITION; CHEMISTRY; CASCADE; SWITCH;

D O I：

10.1021/acs.orglett.9b00277

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Planar chirality inversion of pillar[5]arenes bearing D- or L-alanine substituents on both rims was investigated upon addition of guest molecules having pyridinium or imidazole moieties and long alkyl chains. The D- and L-alanine-substituted pillar[5]arenes exhibited pS and pR planar chirality, respectively. However, this planar chirality was inverted upon inclusion of certain achiral molecules, comprising pyridinium or imidazole moieties and long alkyl chains with terminal hydroxyl or methyl groups.

引用

页码：1232 / 1236

页数：5

共 12 条

[1] Unraveling planar chirality in pillar[5]arenes
Hu, Xiaoyu
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[2] Alignment and Dynamic Inversion of Planar Chirality in Pillar[n]arenes
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (47)
[3] Holding of planar chirality of pillar[5]arene by kinetic trapping using host-guest interactions with achiral guest solvents
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[4] Dynamic-to-Static Planar Chirality Conversion in Pillar[5]arenes Regulated by Guest Solvents or Amplified by Crystallization
Wada, Keisuke
Suzuki, Misaki
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Yamagishi, Tada-aki
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Fa, Shixin
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (19)
[5] Adaptive Planar Chirality of Pillar[5]arenes Invertible by n-Alkane Lengths
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Fa, Shixin
Wada, Keisuke
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[6] Temperature-driven chirality inversion of complexes of bromoalkyl-substituted pillar[5]arenes
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TETRAHEDRON LETTERS, 2023, 125
[7] Pre-regulation of the planar chirality of pillar[5]arenes for preparing discrete chiral nanotubes
Fa, Shixin
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[8] Two pillar[5]arene-based mechanically selflocked molecules (MSMs): planar chirality in crystals and conformer inversion in solutions
Cheng, Ming
Wang, Qi
Cao, Yihan
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Yang, Zhen
Jiang, Juli
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TETRAHEDRON LETTERS, 2016, 57 (37) : 4133 - 4137
[9] Achiral guest-induced chiroptical changes of a planar-chiral pillar[5]arene containing one π-conjugated unit
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[10] Computational Unravelling of the Role of Alkyl Groups on the Host-Guest Complexation of Pillar[5]arenes with Neutral Dihalobutanes
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Jaccob, Madhavan
Solomon, Rajadurai Vijay
CHEMISTRYSELECT, 2018, 3 (04): : 1321 - 1334

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