Chiral effect on the self-assembly of chiral molecules synthesized from cholesterol

Sri Fitriyani, Chun-Yen Liu, Yuyun Yuniarti, Jui-Hsiang Liu

研究成果: Article

摘要

One predesigned chiral steroid base compound cholesteryl 4-(carbonyloxy) 4-(hexyloxyl) benzoate (CCH*) and two achiral compounds with various alkyl chain length oxalyl acid N’,N’-di(4-(hexyloxy)benzoyl)-hydrazide (AG6) and oxalyl acid N’,N’-di(4-(undecyloxy)benzoyl)-hydrazide (AG11) have been successfully synthesized. Formation of asymmetric self-assembled constructions via self-assembly of achiral molecules in chiral environment was investigated. Due to steric hindrance, CCH* could not form gel in any kind of organic solvents. On the other hand, AG6 and AG11 formed achiral gels in many kinds of solvent. The results suggest that polarity, side branch and intermolecular forces are the key factors for the gelation. Temperature-dependent 1H NMR analysis of the fabricated gels show that van der Waals forces and π-π interactions are key factors leading to self-assembly of molecules result in three-dimensional networks. In addition, CCH* was used as a chiral dopant added into achiral compounds forming asymmetric self-assembled constructions. The results indicate that doping of CCH* into achiral gelators giving a chiral environment leads to the formation of helical constructions. The fabricated asymmetric constructions were confirmed using circular dichroism (CD) spectroscopy and small angle X-ray scattering (SAXS).

原文English
頁(從 - 到)481-488
頁數8
期刊Journal of the Taiwan Institute of Chemical Engineers
91
DOIs
出版狀態Published - 2018 十月 1

指紋

Cholesterol
Self assembly
Molecules
Gels
Doping (additives)
Circular dichroism spectroscopy
Van der Waals forces
Acids
Benzoates
Gelation
X ray scattering
Chain length
Organic solvents
Steroids
Nuclear magnetic resonance
Temperature

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

引用此文

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title = "Chiral effect on the self-assembly of chiral molecules synthesized from cholesterol",
abstract = "One predesigned chiral steroid base compound cholesteryl 4-(carbonyloxy) 4-(hexyloxyl) benzoate (CCH*) and two achiral compounds with various alkyl chain length oxalyl acid N’,N’-di(4-(hexyloxy)benzoyl)-hydrazide (AG6) and oxalyl acid N’,N’-di(4-(undecyloxy)benzoyl)-hydrazide (AG11) have been successfully synthesized. Formation of asymmetric self-assembled constructions via self-assembly of achiral molecules in chiral environment was investigated. Due to steric hindrance, CCH* could not form gel in any kind of organic solvents. On the other hand, AG6 and AG11 formed achiral gels in many kinds of solvent. The results suggest that polarity, side branch and intermolecular forces are the key factors for the gelation. Temperature-dependent 1H NMR analysis of the fabricated gels show that van der Waals forces and π-π interactions are key factors leading to self-assembly of molecules result in three-dimensional networks. In addition, CCH* was used as a chiral dopant added into achiral compounds forming asymmetric self-assembled constructions. The results indicate that doping of CCH* into achiral gelators giving a chiral environment leads to the formation of helical constructions. The fabricated asymmetric constructions were confirmed using circular dichroism (CD) spectroscopy and small angle X-ray scattering (SAXS).",
author = "Sri Fitriyani and Chun-Yen Liu and Yuyun Yuniarti and Jui-Hsiang Liu",
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T1 - Chiral effect on the self-assembly of chiral molecules synthesized from cholesterol

AU - Fitriyani, Sri

AU - Liu, Chun-Yen

AU - Yuniarti, Yuyun

AU - Liu, Jui-Hsiang

PY - 2018/10/1

Y1 - 2018/10/1

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AB - One predesigned chiral steroid base compound cholesteryl 4-(carbonyloxy) 4-(hexyloxyl) benzoate (CCH*) and two achiral compounds with various alkyl chain length oxalyl acid N’,N’-di(4-(hexyloxy)benzoyl)-hydrazide (AG6) and oxalyl acid N’,N’-di(4-(undecyloxy)benzoyl)-hydrazide (AG11) have been successfully synthesized. Formation of asymmetric self-assembled constructions via self-assembly of achiral molecules in chiral environment was investigated. Due to steric hindrance, CCH* could not form gel in any kind of organic solvents. On the other hand, AG6 and AG11 formed achiral gels in many kinds of solvent. The results suggest that polarity, side branch and intermolecular forces are the key factors for the gelation. Temperature-dependent 1H NMR analysis of the fabricated gels show that van der Waals forces and π-π interactions are key factors leading to self-assembly of molecules result in three-dimensional networks. In addition, CCH* was used as a chiral dopant added into achiral compounds forming asymmetric self-assembled constructions. The results indicate that doping of CCH* into achiral gelators giving a chiral environment leads to the formation of helical constructions. The fabricated asymmetric constructions were confirmed using circular dichroism (CD) spectroscopy and small angle X-ray scattering (SAXS).

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