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A new series of  shell‐by‐shell  ( SbS )‐functionalized Al 2 O 3  nanoparticles (NPs) containing a perylene core in the organic interlayer as a fluorescence marker is introduced. Initially, the NPs were functionalized with both, a fluorescent perylene phosphonic acid derivative, together with the lipophilic hexadecylphosphonic acid or the fluorophilic (1 H,1 H,2 H,2H‐perfluorodecyl)phosphonic acid. The lipophilic first‐shell functionalized NPs were further implemented with amphiphiles built of aliphatic chains and polar head‐groups. However, the fluorophilic NPs were combined with amphiphiles consisting of fluorocarbon tails and polar head‐groups. Depending on the nature of the combined phosphonic acids and the amphiphiles, tuning of the perylene fluorescence can be accomplished due variations of supramolecular organization with the shell interface. Because the  SbS ‐functionalized NPs dispose excellent dispersibility in water and in biological media, two sorts of NPs with different surface properties were tested with respect to biological fluorescent imaging applications. Depending on the agglomeration of the NPs, the cellular uptake differs. The uptake of larger agglomerates is facilitated by endocytosis, whereas individualized NPs cross directly the cellular membrane. Also, the larger agglomerates were preferentially incorporated by all tested cells.

Smart Shell‐by‐Shell Nanoparticles with Tunable Perylene Fluorescence in the Organic Interlayer