In this study, we report a synthetically simple donor-acceptor (D-A)-type organic solid-state emitter 1 that displays unique fluorescence switching under mechanical stimuli. Orange and yellow emissive crystals of 1 (1O, 1Y) exhibit an unusual "back and forth" fluorescence response to mechanical force. Gentle crushing (mild pressure) of the orange or yellow emissive crystal results in hypsochromic shift to cyan emissive fragments (lambda(em) = 498-501 nm) with a large wavelength shift Delta lambda(em) = -71 to -96 nm, while further grinding results in bathochromic swing to green emissive powder lambda(em) = 540-550 nm, Delta lambda(em) = + 40 to 58 nm. Single-crystal X-ray diffraction study reveals that molecules are packed by weak interactions, such as C-H center dot center dot center dot pi, C-H center dot center dot center dot N, and C-H center dot center dot center dot F, which facilitate intermolecular charge transfer in the crystal. With the aid of structural, spectroscopic, and morphological studies, we established the interplay between intermolecular and intramolecular charge-transfer interaction that is responsible for this elusive mechanochromic luminescence. Moreover, we have also demonstrated the application of this organic material for chlorine gas sensing in solid state.