Covalent functionalization tailors carbon nanotubes for a wide range of applications in varying environments. Its strength and stability of attachment come at the price of degrading the carbon nanotubes sp2 network and destroying the tubes electronic and optoelectronic features. Here we present a non-destructive, covalent, gram-scale functionalization of single-walled carbon nanotubes by a new [2+1] cycloaddition. The reaction rebuilds the extended π-network, thereby retaining the outstanding quantum optoelectronic properties of carbon nanotubes, including bright light emission at high degree of functionalization (1 group per 25 carbon atoms). The conjugation method described here opens the way for advanced tailoring nanotubes as demonstrated for light-triggered reversible doping through photochromic molecular switches and nanoplasmonic gold-nanotube hybrids with enhanced infrared light emission.

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A fundamental issue for biomedical applications of graphene is the correlation between its physicochemical properties and cellular uptake mechanism. However, such studies are challenging due to the intrinsic polydispersity of graphene. In this work, a series of water soluble graphene sheets with the same polymer coverage, density of functional groups, and fluorescence intensity but three different sizes and surface charges are produced. The effect of the latter two factors and their combination on the mechanism of cellular uptake and intracellular pathways of these defined nanosheets is investigated via confocal and Raman microscopies. While positively (NH3+) and negatively (OSO3−) charged sheets show an energy dependent uptake, their neutral analogs do not show any significant uptake. The cellular uptake efficacy of positively charged graphene sheets is independent of the size and occurs both through phagocytosis and clathrin‐mediated endocytosis pathways. However, cellular uptake efficacy of graphene sheets with negative surface charge strongly depends on the size of the sheets. They cross the membrane mainly through phagocytosis and sulfate‐receptor‐mediated endocytosis. This study demonstrates that the impact of the size of graphene derivatives on their cellular uptake pathways highly depends on their surface charges and vice versa.