(N‐Phenylfluorenylidene)acridane (Ph‐FA) compounds with electron‐withdrawing and ‐donating substituents (H, MeO, Ph, NO2, Br, F) at the para position of the phenyl group were successfully synthesized by Barton–Kellogg reactions of N‐aryl thioacridones and diazofluorene. By using the substituent on the nitrogen atom to alter the electronic properties, both the folded and twisted conformers of p‐NO2‐C6H4‐FA could be crystallographically characterized, which enabled the charge transfer from the electron‐donating acridane moiety to the electron‐accepting fluorenylidene moiety to be understood. Ground‐state mechanochromism, thermochromism, vapochromism, and proton‐induced chromism were demonstrated between the folded and twisted conformations of the conformers. Protonation and chemical oxidation of Ph‐FA gave two stable acridinium compounds, namely, the fluorenylacridinium and acridinium radical cations. The present study will contribute to the development of functional dyes and organic semiconductors. Farbkontrolle: N‐(Phenylfluorenyliden)acridan‐Verbindungen mit elektronenziehenden und ‐schiebenden Substituenten an der para‐Position der Phenylgruppe wurden synthetisiert und mittels Röntgenkristallstrukturanalyse der gefalteten und verdrehten Konformere des Nitro‐Derivats bestimmt. Die Verbindungen zeigen verschiedene Farb‐ und Ladungsträgertransport‐Eigenschaften.