Abstract

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.

Highlights

  • Covalent functionalization tailors carbon nanotubes for a wide range of applications in varying environments

  • Bio-imaging greatly benefits from the wavelength at which single-walled carbon nanotubes (SWNTs) emit light; it lies in the second window of tissue transparency (1,100–1,400 nm) with a large penetration depth, but low tissue scattering and autofluorescence[6,7]

  • Optoelectronic applications heavily rely on the read-out of the SWNT fluorescence

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Summary

Ring opening and rehybridization

Even at highest functionalization (SWNT-high, one triazine ring per 25 carbon atoms) the ratio remained identical to the pristine material ID/IG 1⁄4 0.1, proving that no conversion of C atoms from sp[2] to sp[3] occurred. The overall twodimensional luminescence intensity of SWNT-high is identical to that of the pristine tubes (Fig. 2d). Some functionalized species show even brighter emission than their pristine counterparts (compare, for example, the (9,4) tube in the left and right panel of Fig. 2d). Sensing and imaging in biological environment, on the other hand, benefit from enhanced overall emission With such applications in mind, we present two functional examples for covalently tailored luminescent SWNTs: A conjugated photochromic molecular switch to control the emission from the SWNTs and covalently attached AuNPs to plasmonically enhance the nanotubes optical response. Under ultraviolet irradiation the SP-functionalized SWNTs (SP-SWNTs) hybrids convert into MC-SWNTs by the molecular

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