Herein, we report the synthesis, self-assembly, and electroluminescence characteristics of a new green-emitting, pseudodiscoid chiral molecule, OXDC, containing an electron-donating stilbene core and an electron-accepting oxadiazole substituent. The helical organization and specific interaction of the chiral pseudodiscoid molecule resulted in the formation of self-assembled nanofibers with a columnar superstructure. Macroscopic chirality was observed in both the liquid-crystalline phases and the self-assembled nanofibers of OXDC, a feature which was absent in the analogous achiral oxadiazole derivative reported earlier [Sivadas, A. P.; et al. Supergelation via Purely Aromatic pi-pi Driven Self-Assembly of Pseudodiscotic Oxadiazole Mesogens. J. Am. Chem. Soc. 2014, 136, 5416-5423]. A high-performance organic light-emitting device was demonstrated using OXDC as the emitting material, with a luminous intensity of 10 115 cd m(-2) at 5 V and chromaticity coordinates of (0.32, 0.51).