Journal
ORGANIC LETTERS
Volume 8, Issue 14, Pages 3009-3012Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol060923k
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- NIGMS NIH HHS [S06 GM 08194] Funding Source: Medline
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[GRAPHICS] Azophenol dyes having the permethylated cyclodextrin and/or crown moieties have been synthesized. Compound 1 provides critical information on discriminating 1-3 degrees amines with unique color changes. Addition of 1 degrees and 2 degrees amines to 1 shifts the absorbance maximum of 1 from 380 to similar to 580 and similar to 530 nm, respectively, but no change is observed with 3 degrees amines. The high selectivity of 1 is mainly due to H-bonding between the ammonium H atoms of the amine and oxygen atoms of the crown-6.
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