The fabrication of modern microelectronic silicon devices mechanically challenges these thin silicon substrates during manufacturing operations. Melt and solution polyesterification enabled the synthesis of polyesters containing photoreactive o-nitro benzyl ester units for use as a potential photocleavable adhesive. Melt transesterification provided a solvent-free method for synthesis of 2-nitro-p-xylylene glycol (NXG)-containing polyesters of controlled molecular weights. 1 H NMR spectroscopy confirmed the chemical composition of the photoactive polyesters. Size exclusion chromatography (SEC) determined the number-average molecular weights (M n ) of the polyesters synthesized in the range of 6000 to 12000 g=mol. 1 H NMR spectroscopy confirmed increasing levels of photocleavage of the o-nitro benzyl ester functionality with increasing exposure to broad wavelength UV irradiation, and exposure levels ranged from 0-187 J=cm 2 UVA. Photocleaveage of approximately 90% of the o-nitro benzyl ester (ONB) units within the backbone of the polymer occurred at maximum dosage. Wedge fracture testing revealed approximately a two-fold decrease in fracture energy upon UV irradiation, suggesting that these structural adhesives offer potential for commercial ''flip bonding'' applications.