This Letter reports some interesting results on twisted intramolecular charge transfer emission of 4-N,N-dimethylaminocinnamic acid complexed with alpha -cyclodextrin. Salient features of this investigation, as revealed from twisted intramolecular charge transfer emission intensity and position dependence on alpha -CD concentration, are the formation of 1:2 barrel-shaped complex in addition to 1:1complex, while twisted intramolecular charge transfer (TICT) band intensity shows an increase and then a sharp decrease (bell-shaped variation) along with blue shift and initial addition of base to the solution obstructs the formation of 1:2 complex.