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The unconventional self-assembled nanodielectric (SAND) architecture is composed of solution-processed alternating inorganic (e.g., ZrOx and HfOx) and π-organic nanolayers (e.g., stilbazolium). As gate dielectrics, SANDs are compatible with a wide variety of organic and inorganic semiconductors and often impart superior thin-film transistor (TFT) performance in comparison to analogous inorganic-only dielectrics. The enhanced performance has been partly attributed to the interactions within the organic layers. To probe the role of the highly polarizable stilbazolium (Chr) organic layer in SAND structural organization and dielectric response, a saturated hydrocarbon chain-based self-assembling building block (Alk) was synthesized and incorporated in SAND structures. By using Chr and Alk in the different SAND organic layers, the effects of the Chr built-in dipole on bulk SAND structural and dielectric characteristics can be evaluated. The Zr-SAND structures are characterized by atomic force microscopy, X-ray reflectivity, metal-insulator-semiconductor electrical measurements, and pentacene-based organic TFTs. The layer identity and arrangement of the organic layers within the Zr-SAND structure are found to have a significant impact on the capacitor leakage current and pentacene transistor threshold voltage/turn-on voltage characteristics. Furthermore, significant cooperative interactions between adjacent Chr organic π-layers are important in enhancing these effects.