A chemosensor having electron pushing donor and pulling acceptor material based on conjugation bridges, namely D-pi-A structural chemosensor, was herein designed and synthesized. This chemosensor 3 contained guajazulene and indole moieties, which was synthesized through a one-step condensation reaction. The synthesized material showed very selective sensing properties towards anions. Upon the addition of CN- and F-, the remarkable changes in absorption spectra were monitored. However, each of others did not show any noticeable optical changes. The original intramolecular charge transfer system of chemosensor 3 was altered by the formation of N- at iindole moiety with anion reaction: caused by the deprotonation of NH at the indole moiety of chemosensor. With intermolecular charge transfer system between chemosensor 3 and anions, the electron density and distribution were determined by frontier calculation method.