Chromaticity sensor for discriminatory identification of aliphatic and aromatic primary amines based on conformational changes of polyacetylene

Abstract

The design and construction of suitable sensors that can selectively recognize chemically similar substances such as aliphatic and aromatic amines remain challenging. In this work, we reported a poly(phenylacetylene) bearing two aldehyde pendants as the color indicator for discriminative identification of amines. Reversible Schiff-base reaction of the aldehyde group with the amine resulted in a conformational transition of the polyacetylene backbone from cis-cisoid to cis-transoid, which further achieved a colorimetric change. Thirteen aliphatic amines and aromatic amines had been studied. Compared with aromatic amines, aliphatic amines generally caused the polyene backbone to display perceivable colorimetric change. Steric and electronic effect played a significant role in the colorimetric response. In addition, external environment, including amine content, polymer concentration, and temperature, had influence on the sensitivity of this colorimetric indicator system. The amines-induced colorimetric variation was further demonstrated by the CIELAB color space. Moreover, the colorimetric sensor exhibited excellent reversibility and recyclability.