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Oxidation scanning probe lithography was used to systematically fabricate graphene/defective graphene ribbon arrays on a graphene sheet. The tribological, structural, and chemical natures of the defects created by o-SPL were characterized using lateral force microscopy (LFM), micro-Raman (μ-RS) and micro-X-ray spectroscopy (μ-XPS), respectively. While LFM revealed all fabricated patterns exhibited increase in friction, μ-RS and μ-XPS analysis showed that a transition of defect type from structural to chemical defects occurred in the defective graphene ribbons at a threshold voltage (8.5 V). Subsequently, micro-photoluminescence (μ-PL) quenching spectroscopy was measured for a thin layer of polystyrene containing isolated fluorophores (MEH-PPV) spin cast on the ribbon patterns. Whilst the quenching efficiency was suppressed more significantly as defect concentration increased, for pure structural defects, the μ-PL lifetime varied linearly with defect concentration and then saturated to a constant as chemical defects dominated. Among all oxygen related functional groups, the presence of C[dbnd]O bonds led to greatly reduced quenching efficiency while simultaneously reducing the strong blue spectral shift seen for pure graphene with the spectrum at higher C[dbnd]O bond concentration approaching to pristine MEH-PPV. This work demonstrated that local chemical and structural composition in 2D quencher strongly affects the quenching efficiency and dynamics.