The current dental restorations suffer from reduced longevity mainly due to interfacial breakdown. The premature failure in this area leads to microleakage, sensitivity, recurrent caries, restoration removal/replacement, and extensive loss of sound tooth structure. The annual cost for replacement in dentistry is about $5 billion in the USA, accounting for nearly 75% of all operative dentistry. The causes of interfacial breakdown have been summarized in the literature as (1) poor quality of adhesive infiltrated into the dentin collagen; (2) low interfacial stress-absorbing potential; (3) degradation of adhesive by bacterial acids at the tooth/restoration interface; and (4) degradation of unprotected collagen fibrils by endogenous MMPs. Thus, there is an increased need to develop a new generation of multifunctional dental adhesives to improve their properties and longevity. Therefore, the specific aims of this dissertation are (1) to perform a critical review of the degradation and failure phenomena at the dentin bonding interface to capture the underlying mechanisms; (2) systematically reviewed the recent studies on core-shell nanostructures incorporated into dental resin-based materials, their intended properties, synthesis methods, and assessment tests employed; (3) design and synthesize multifunctional core-shell nanoparticles for dental adhesives with a magnetic-guided motion for chlorhexidine delivery; and (4) evaluate the incorporation of core-shell nanoparticles into Bis-GMA/HEMA dental adhesives and the impact on the core properties of dental adhesives and the antibacterial outcome performance. This platform is intended to combine better adhesive infiltration by magnetic motion, resistance against bacterial bond degradation processes, and additional bioactive potential in light of the clinically relevant desired antibacterial and anti-MMPs properties. The multifunctional platform was synthesized using the modified sol-gel method, then characterized. First, the CHX loading/releasing profiles were measured using UV-Vis spectroscopy, TGA/DTA, and HPLC. Then, the antibacterial properties were tested against S.mutans biofilms, the most studied bacterium causing dental caries. The multifunctional platform was successfully synthesized, and the CHX release was increased over time with higher amounts in a neutral environment. Moreover, the platform did not affect the cell viability of HGF and DPSC. After that, the platform was incorporated into the dental adhesive, and assessed the impact on core properties required for a satisfactory performance inside the mouth. We found that the overall performance of the adhesive containing iron oxide/mesoporous silica core-shell nanostructures is reached with concentrations 4 and 5 wt.%. Lastly, we investigated the long-term performance following artificial aging. The newly synthesized adhesives have efficiently inhibited S.mutans and slightly decreased the microtensile bond strength to dentin compared to the baseline results. The triple benefits of reinforcement, antibacterial, and anti-MMPs have great potential to assist the long-term performance of bonded restorations.