We report the synthesis, characterization, and application of novel zwitterions. The zwitterionic structures consist of a positively charged cyanine and negatively charged dienolate moieties, confirmed by experimental observations and theoretical calculations. Single crystal X-ray studies revealed that BIT-(NPh)(2) is a coplanar molecule that forms 1-D chains via pi-pi interactions. In contrast, BIT-(NHexyl)(2) is a twisted molecule with a dihedral angle of 78 degrees between the charged planes. In charge transport studies, thin films of the flat zwitterion show semiconducting properties, with a hole mobility of 2.1 X 10(-4) cm(2) V-1 s(-1) while the twisted zwitterion is a high resistivity insulator.