Gang Lu, Jonathan E. Grossman, J. B. Lambert
Feb 9, 2006
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0
Influential Citations
42
Citations
Journal
The Journal of organic chemistry
Abstract
Aliphatic amines are sensitively and discriminatively detected through binding with demethylated naphthol AS-BI (7-bromo-3-hydroxy-2-naphth-o-hydroxyanilide, 2) and fluorescence of the resulting complex. Recognition of the amine by the chemosensor 2 occurs via proton transfer of the naphtholic proton to the amine and is facilitated by the presence of the phenol group. Amine basicity is the primary controller of detection. Poorly basic aromatic and conjugated amines such as pyridine and aniline are not detected. Hydrogen bonding within the complex allows further differentiation of aliphatic amines. Doubly primary, conformationally flexible diamines are the most sensitive to detection, followed by secondary amines.