Synthetic materials exhibiting contrast imaging properties have become vital to the field of biomedical imaging. However, polymeric biomaterials are lacking imaging contrast properties for deep tissue imaging. this report details the synthesis and characterization of a suite of aryl-iodo monomers, which were used to prepare iodinated polyesters using a pre-functionalization approach. commercially available 4-iodo-phenylalanine or 4-iodobenzyl bromide served as the starting materials for the synthesis of three iodinated monomeric moieties (a modified lactide, morpholine-2,5-dione, and caprolactone), which under a tin-mediated ring-opening polymerization (Rop), generated their respective polyesters (pe) or poly(ester amides) (peA). An increase in X-ray intensity of all synthesized iodine-containing polymers, in comparison to non-iodinated poly(lactic acid) (pLA), validated their functionality as radio-opaque materials. the iodinated-poly(lactic acid) (ipLA) material was visualized through varying thicknesses of chicken tissue, thus demonstrating its potenial as a radio-opaque biomaterial. Medical imaging, a technique that provides structural visualization inside the body, aides in the study of specific morphological changes within living and nonliving systems 1,2. One particular imaging modality, X-ray radiography, is frequently used as a diagnostic tool for non-invasive, in vivo, real-time examinations of three-dimensional opaque objects. X-ray imaging can be used to monitor response, degradation, and defects of biomedical devices 3. Concerns over the long-term stability of prolonged or permanent implantable devices have led to the development of polyester-based materials due to their desirable properties (i.e. biocompatibility, biodegradability, and facile synthesis) 4-8. The evolution of biodegradable polyester devices, like staples, stents, sutures, and implants, have had a significant impact on the biomedical field 4,9,10. Perhaps the most noteworthy advantage is their ability to be degraded and excreted from the body, obviating the need for their removal or surgical revision. This can be vital in major surgical procedures such as fracture fixation, spinal fixation, and abdominal wall repair 4,10. While commercially available polyester devices have seen a considerable amount of use in the biomedical field, their in vivo performance can be difficult to predict and evaluate due to the complex biological environment associated with tissues 10,11. Therefore, the real-time monitoring of these devices is critical in order to understand their performance and fate in the body. The major drawback of polyester-based devices is that they lack inherent contrast imaging properties, making it difficult to visualize the area of interest. Imaging techniques are useful only when the intensity of a signal is sufficient enough to distinguish the target from surrounding tissues or materials. This issue becomes even more evident when imaging materials through deep tissue or when monitoring minor defects in biomaterials 12. Recent ...