A novel perylene diimide (PDI) derivative with typical amphiphilic character, 2, was designed and prepared. The spectroscopic studies on this compound in solution revealed the face-to-face dimeric configuration and effective pi-pi interaction between the two perylene rings. This amphiphilic PDI derivative was fabricated into highly ordered films by Langmuir-Blodgett (LB) technique and fabricated into an organic field effect transistor (OFET), which shows carrier mobility around 0.05 cm(2) V(-1) s(-1) and current modulation of 10(3). This OFET performance is much better than that of monomeric PDI 1 and can be attributed to the unique face-to-face structure of 2, which promotes the interactions between neighboring PDI ring in LB film as indicated by the pi-A isotherms and UV-vis absorption.