Bifunctional maleimide dyes as selective anion sensors

A class of disubstituted maleimide dyes with two symmetrical NH binding sites was found to exhibit distinct color change and fluorescence quenching effect for fluoride, cyanide, and dihydrogen phosphate anions. The intense red emission displayed apparent solvatochromic shift, indicating a strong charge-transfer character. The interactions between the dyes and anions were variable depending on the amine substituents at C(3,4) of the maleimides. For the dyes with two pyrrolyl receptor sites, the NH protons were deprotonated by more basic anions such as fluoride or cyanide. For those with two indolyl receptor sites, formation of a chelate with H2PO4− through hydrogen bonds played a major role.