Visual chiral recognition of 1,1′-binaphthol through enantioselective collapse of gel based on an amphiphilic Schiff-base gelator

doi:10.1007/s11705-017-1633-3

Front. Chem. Sci. Eng.

2017, Vol. 11

Issue (2) : 231-237 https://doi.org/10.1007/s11705-017-1633-3

RESEARCH ARTICLE

Visual chiral recognition of 1,1′-binaphthol through enantioselective collapse of gel based on an amphiphilic Schiff-base gelator

Xuhong Zhang, Haimiao Li, Xin Zhang, Meng An, Weiwei Fang, Haitao Yu(

)

College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024, China

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Abstract

A novel gelator that contained both Schiff base and L-lysine moieties was synthesized and its gelation behavior was tested. This gelator can form gels in various organic solvents. The resulting gel can be applied as a fascinating platform for visual recognition of enantiomeric 1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol (BINOL) through selective gel collapse. In addition, the mechanism for the reaction of the gel with chiral BINOL was investigated by scanning electron microscope and ¹H nuclear magnetic resonance.

Keywords gelator Schiff base chiral recognition gel formation gel collapse

Corresponding Author(s): Haitao Yu

Just Accepted Date: 15 February 2017 Online First Date: 06 April 2017 Issue Date: 12 May 2017

Cite this article:

Xuhong Zhang,Haimiao Li,Xin Zhang, et al. Visual chiral recognition of 1,1′-binaphthol through enantioselective collapse of gel based on an amphiphilic Schiff-base gelator[J]. Front. Chem. Sci. Eng., 2017, 11(2): 231-237.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-017-1633-3
https://academic.hep.com.cn/fcse/EN/Y2017/V11/I2/231

Fig.1 Scheme 1&chsp;Synthesis of the gelator 1.(i) Hydrazine hydrate, methanol, reflux, 8 h, 40.7%; (ii) salicylaldehyde, ethanol, reflux, 8 h, 77.1%

Fig.2 Chemical structures of 1, (S)- and (R)-BINOL

Tab.1 Gelation ability of 1 in various solvents in air at 25 °C

Fig.3 (a) SEM image of xerogel obtained from the gel of 1 in morpholine; (b) FTIR spectra of gel of 1 in morpholine

Fig.4 SEM images of xerogels obtained from the gels (35 mg/mL) of 1 in aniline (left) and in nitrobenzene (right)

Fig.5 Visual chiral recognition of (R)-BINOL and (S)- BINOL through gel 1/ morpholine (3.2 wt-%) enantioselective collapsing: (a) gel of (1+1.5 equiv (S)-BINOL), and (b) suspension of (1+1.5 equiv (R)-BINOL)

Fig.6 SEM images of (a) gel of (1+1.5 equiv (S)-BINOL)/morpholine and (b) suspension of (1+1.5 equiv (R)-BINOL)/morpholine

Fig.7 Partial ¹H NMR (500 MHz) spectra of compound 1 (12 mmol/L) and its complexes with the enantiomers of BINOL in CDCl₃ at 25 °C: (a) (S)-BINOL, (b) (R)-BINOL, (c) only compound 1, (d) 1+ (S)-BINOL (1.5 equiv), and (e) 1+ (R)-BINOL (1.5 equiv)

Fig.8 Partial ¹H NMR (500 MHz) spectra of (a) morpholine (0.05 mL), (b) gelator 1 (1.7 mg, 3.2 wt-% in morpholine), (c) morpholine+ gelator 1, and (d) morpholine+ gelator 1 + 1.5 equiv. (R)-BINOL in CDCl₃ (0.45 mL) at 25 °C

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