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

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

Research output: Contribution to journalArticlepeer-review

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).

Original languageEnglish
Pages (from-to)481-488
Number of pages8
JournalJournal of the Taiwan Institute of Chemical Engineers
Volume91
DOIs
Publication statusPublished - 2018 Oct

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

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