Red and near infrared (NIR) emission light is a highly desirable feature for fluorescent nanoparticles in biological applications mainly due to longer wavelengths more easily being able to penetrate tissues, organs, skin, and other organic components. Additionally, graphene quantum dots (GQDs) that contain unique optical and electrical features have been targeted for their use in cell labeling applications as well as environmental analysis. Their most desirable features come in the form of low toxicity and biocompatibility; however, GQDs are frequently reported to have blue or green emission light and not the more advantageous red/NIR emission light. Furthermore, porphyrins are a subgroup of heterocyclic macrocycle organic compounds and have been used previously to synthesize nanomaterials and for nanoparticle doping in order to incorporate the red/NIR emission light property into particles that otherwise do not contain the desired emission light. Meso-tetra(4-carboxyphenyl)porphine (TCPP) is one type of porphyrin with a large conjugated π-electron system and four carboxyl groups on its exterior benzene rings. These two key characteristics of TCPP makes it ideal for incorporation into GQDs as it would design and synthesize red-emissive material as well as give rise to excellent water solubility. In this work, TCPP is used together with cis-cyclobutane-1,2-dicarboxylic acid (CBDA-2), a biomass derived organic molecule, to synthesize “green” porphyrin-based graphene quantum dots (PGQDs) with red-emission light for in vitro and in vivo confocal microscopy cell imaging and metal ion detection.

Synthesis of red-emissive porphyrin-based biomass-derived graphene quantum dots for in vitro and in vivo cell imaging and metal ion detection

ACS Fall 2021

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