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Amphiphilic Schiff Base Organogels: Metal‐Ion‐Mediated Chiral Twists and Chiral Recognition
Author(s) -
Jin Qingxian,
Zhang Li,
Zhu Xuefeng,
Duan Pengfei,
Liu Minghua
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103187
Subject(s) - schiff base , metal ions in aqueous solution , amphiphile , fluorescence , ion , quenching (fluorescence) , tartaric acid , metal , polymer chemistry , chemistry , materials science , nuclear chemistry , organic chemistry , copolymer , polymer , citric acid , physics , quantum mechanics
New amphiphilic gelators that contained both Schiff base and L ‐glutamide moieties, abbreviated as o ‐SLG and p ‐SLG, were synthesized and their self‐assembly in various organic solvents in the absence and presence of metal ions was investigated. Gelation test revealed that o ‐SLG formed a thermotropic gel in many organic solvents, whilst p‐ SLG did not. When metal ions, such as Cu 2+ , Zn 2+ , Mg 2+ , Ni 2+ , were added, different behaviors were observed. The addition of Cu 2+ induced p‐ SLG to from an organogel. In the case of o‐ SLG, the addition of Cu 2+ and Mg 2+ ions maintained the gelating ability of the compound, whilst Zn 2+ and Ni 2+ ions destroyed the gel. In addition, the introduction of Cu 2+ ions caused the nanofiber gel to perform a chiral twist, whilst the Mg 2+ ions enhanced the fluorescence of the gel. More interestingly, the Mg 2+ ‐ion‐mediated organogel showed differences in the fluorescence quenching by D ‐ and L ‐tartaric acid, thus showing a chiral recognition ability.