A novel triphenylamine based oxidative chemosensor TOC was synthesized. The chromogenic and fluorogenic behaviors of TOC towards Hg2+ and Cu2+ ions in a binary mixture of MeCN/H2O (9/1) were dramatically different. TOC displays colorimetric 'naked eye' recognition of Hg2+ and fluorogenic 'turn on' response towards Cu2+ via a unique cyclization reaction using two different detection modes. Moreover, TOCAZOL obtained from the oxidative cyclization reaction of TOC with Cu(ClO4)2 can be used as a selective fluorescent sensor toward Hg2+ ion.