To create lowb and-gap,f luorescent, and elastic organic crystal emitters,w ef ocused on an extended pconjugated system based on:a )aplanar conformation,b) arigid structure,and c) controlled intermolecular interactions. Herein, we report on two fluorescent and highly flexible organic crystals (1 and 2)whichcould bend under an applied stress.T he bent crystals rapidly recover their straight shape upon release of the stress.C rystal 1 with at etrafluoropyridyl terminal unit and al ower band-gap energy (orange emission, l em = 573 nm, F F = 0.50), showed no bending mechanofluorochromism and had superior performance as an optical waveguide with reddish orange emission. The waveguide performance of the crystal did not decrease under bending stress.F or crystal 2 with ap entafluorophenyl terminal unit (green emission, l em = 500 nm, F F = 0.38), the original waveguide performance decreased under an applied bending stress; however,this crystal showed aunique bending mechanofluorochromism.