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. 2016 Nov 24;16(12):1985.
doi: 10.3390/s16121985.

One-Pot Click Access to a Cyclodextrin Dimer-Based Novel Aggregation Induced Emission Sensor and Monomer-Based Chiral Stationary Phase

Xiaoli Li  1   2 , Rui Zhao  3   4 , Xiaoying Tang  5   6 , Yanyan Shi  7   8 , Chunyi Li  9 , Yong Wang  10   11
Affiliations

One-Pot Click Access to a Cyclodextrin Dimer-Based Novel Aggregation Induced Emission Sensor and Monomer-Based Chiral Stationary Phase

Xiaoli Li et al. Sensors (Basel). .

Abstract

A 'two birds, one stone' strategy was developed via a one-pot click reaction to simultaneously prepare a novel cyclodextrin (CD) dimer based aggregation induced emission (AIE) sensor (AIE-DCD) and a monomer based chiral stationary phase (CSP-MCD) for chiral high performance liquid chromatography (CHPLC). AIE-DCD was found to afford satisfactory AIE response for specific detection of Zn2+ with a detection limit of 50 nM. CSP-MCD exhibits excellent enantioseparation ability toward dansyl amino acids, where the resolution of dansyl amino leucine reaches 5.43.

Keywords: aggregation induced emission; chiral stationary phase; click; cyclodextrin.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
‘One-pot’ click synthetic pathway of the AIE-CD dimer sensor (TPE-2triazole-2CD) and monomer CD-CSP (Triazole-CD-CSP).
Figure 1
Figure 1
(a) Fluorescence emission spectra for solution of TPE-2triazole-2CD (50 μM) in different ratios of DMSO/H2O (λex = 330 nm, ex/em slits = 5/5); (b) Fluorescence response of the sensor (50 mM) in different solvent compositions of H2O/DMSO at 475 nm (λex = 370 nm).
Figure 2
Figure 2
(a) The FL intensity of TPE-2triazole-2CD (50 μM) in DMSO/H2O (2/3, v/v) in the presence of 5 equivalent of different metal ions; (b) Fluorescence response of the sensor (50 μM) to 0.5 equivalent of metal ions (the green bar) and to the mixture of 0.5 equivalent of other metal ions with 0.5 equivalent of Zn2+ (the blue bar) and the fluorescence response of TPE-2triazole-2CD toward Zn2+ + all metal ions (the red bar) (λex = 330 nm, λem = 478 nm).
Figure 3
Figure 3
(a) Fluorescence emission spectra change of TPE-2triazole-2CD exposed to Zn2+ of various concentrations: 0, 0.5, 1, 2.5, 5, 7.5, 10, 12.5, 15, 17.5, 20.0, 25, 37.5, 50 μM from bottom to top (DMSO/H2O = 2/3, v/v); (b) Fluorescence titration curve of TPE-2triazole-2CD with Zn2+ in DMSO-H2O (2/3, v/v) solution.
Figure 4
Figure 4
Possible proposed mechanistic pathway for sensing Zn2+ ion-based on Aggregation Induced Emission.
Figure 5
Figure 5
Representative chromatograms on Triazole-CD-CSP. Conditions: 1% TEAA buffer (pH 4.11)/MeOH (50/50 v/v); flow rate = 0.8 mL/min. (a) Dansyl amino leucine; (b) Dansyl amino methionine.
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