A new class of tailor-made push-pull isoindole fluorophores has been synthesized through the combination of Suzuki coupling and Knoevenagel reactions. The efficient synthetic strategy rendered the isoindole scaffold as the π-bridge and the isolation spacer and provided dyes bearing various types of electron donors and electron acceptors for manipulating their energy gaps and tuning their absorptions and emissions. Most of the N-alkylated isoindole dyes showed aggregation-induced emission behaviors suitable for bioimaging and nice solid-state emission with maxima up to 851 nm.