alpha-CD/crown-appended diazophenol for selective sensing of amines

[reaction: see text] 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 approximately 580 and approximately 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.