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. 2007 Jan 5;72(1):97-101.
doi: 10.1021/jo061769i.

Enantioselective fluorescent recognition of amino alcohols by a chiral tetrahydroxyl 1,1'-binaphthyl compound

Qin Wang  1 , Xi Chen, Lan Tao, Li Wang, Dan Xiao, Xiao-Qi Yu, Lin Pu
Affiliations

Enantioselective fluorescent recognition of amino alcohols by a chiral tetrahydroxyl 1,1'-binaphthyl compound

Qin Wang et al. J Org Chem. .

Abstract

The tetrahydroxyl derivative of BINOL, (S)- or (R)-1, and its analogues are synthesized. (S)- or (R)-1 can be used to conduct the enantioselective recognition of chiral amino alcohols. In comparison with BINOL, the two additional hydroxyl groups of (S)- or (R)-1 have increased the binding of this compound with the amino alcohols and significantly improved the fluorescence quenching efficiency. The fluorescence responses of (S)- or (R)-1 toward amino alcohols are compared with those of its analogues (R)-4 and (R)-6. It shows that the interaction of the central naphthyl hydroxyl groups of (S)- or (R)-1 with the substrates is responsible for the observed fluorescence quenching, and the two additional alkyl hydroxyl groups increase the quenching efficiency.

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Figures

Figure 1
Figure 1
Fluorescence Spectra of (R)-BINOL, (R)-1, (R)-4 and (R)-6 in CH2Cl2 (8.0 × 10−6 M, λexc at 294, 298, 298 and 302 nm, respectively, emission slits: 5.0 nm).
Figure 2
Figure 2
Fluorescence Spectra of (R)-1 and (R)-BINOL (both at 1.0 × 10−5 M) in CH2Cl2/hexane (30:70) with and without (R)-7 (8.0 × 10−3 M) (λexc at 298 and 300 nm respectively).
Figure 3
Figure 3
Stern-Völmer Plot of (R)-1 (1.0 × 10−5 M) in CH2Cl2/hexane (30:70) in the presence of (R)- and (S)-7 (λexc = 298 nm).
Figure 4
Figure 4
Stern-Völmer Plot of (S)-1 (1.0 × 10−5 M) in CH2Cl2 in the presence of (R,R)- and (S,S)-11 (λexc = 255 nm).
Scheme 1
Scheme 1
Synthesis of the Tetrahydroxyl 1,1′-Binaphthyl (R)-1.
Scheme 2
Scheme 2
Synthesis of (R)-4.
Scheme 3
Scheme 3
Synthesis of (R)-6.
See this image and copyright information in PMC

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