An organometallic coupling electrophile-induced cyclization strategy for the synthesis of p-terphenyl compds. has been extended to the synthesis of p-quinquephenyl systems. In this work the authors report the synthesis of various polycyclic arom. systems contg. nine annelated rings including the synthesis of functionalized polycyclic arom. systems. An interesting side reaction which leads to an indenyl spiro ring system is also described. This side reaction can be suppressed by changing the electrophile (from H+ to I+) or by modification of the cyclization precursor. The UV-vis and fluorescence spectra of several of these polycyclic aroms. and the p-quinquephenyl precursors are also reported. [on SciFinder(R)]