Given the wide-spread usage of bipyridines and 2-phenyl pyridines as ligands or ligand precursors, we reasoned that the obtained spirocycles can be connected to a metal center to impart intriguing material properties. By utilizing products 8q and 8b, we rapidly accessed the chiral variants of widely applied copper-based light-emitting electrochemical cells (LEC) and platinum-based organic light-emitting diodes (OLEDs) , 11a and 11b, respectively (Fig. ). The luminescence properties of 11a and 11b were analyzed and fluorescence lifetimes and quantum yields compared well with literature (Fig. , Table ). To further showcase the utility of the process with complex molecules displaying intriguing chiroptical properties, we prepared a chiral C2-symmetric bis-spiro fluorene 11c with a highly conjugated heptacyclic core in a rapid synthetic sequence. Bis-pyridine 8ab was prepared in 95% yield with an 87:13 dr and >99:1 er by a double enantioselective [2+2+2] heterocyclization of 1,4-dicyanobenzene with dialkyne 1d. A double pyridine-directed electrophilic borylation gave tetrabromide 8ac. Subsequent treatment of 8ac with AlMe3 exhaustively replaced all four bromides by methyl groups leading to compound 11c in 50 % yield. The photophysical and advanced chiroptical properties of 11c were measured. (Fig. ) The emission spectrum of 11c ranges from 350 nm to 650 nm, with three prominent maxima, the maximum was blue shifted in solid state by ~2820 cm -1 . The fluorescence lifetimes of 11c are on a microsecond scale which are similar to the known thermally activated delayed fluorescence (TADF) materials (Table ). Notably, compound 11c exhibited an appreciable CPL activity, with a dissymmetric factor |glum| = 1.5 × 10 -3 at 490 nm (Fig. & Fig. ). The value of the important dissymmetric factor of 11c is of similar magnitude than the ones of existing chiral organic dyes as well as helicenes.