In massively multi core System on Chips (SoCs), high throughput, low delay and fault tolerance are essential factors to fully harness the computational power offered by tens and hundreds of Processing Elements (PEs). Network on Chips (NoCs) have emerged as a recognized solution to fulfill the ever growing communication demands to interconnect the PEs in modern SoCs.A number of topologies have been proposed in the literature to meet the communication demands of SoCs. In this thesis we proposed and evaluated a novel self similar and highly scalable NoC topology (called PentaNoC) with desirable topological properties including, low node degree, low average hop count, low diameter and high path diversity as well as bisection width. The new topology is based on cascading and interconnecting any number of pentagon shape blocks. The research involved formulating the topological properties of the proposed topology, devising a deadlock free routing protocol and comparing the performance of the proposed topology with its counterparts both analytically and experimentally.Analytically, against three topologies, the PentaNoC topology showed better results in terms of having the smallest average hop count and diameter, and the maximum bisection width.Experimentally, and under different set of parameters, the proposed topology and two of its counterparts were tested and statistics were collected to evaluate their performance. The PentaNoC showed better results than its opponents in small network sizes and the difference is theoretically expected to grow bigger with the growth of the network's size in favor of the PentaNoC.