Functional macromolecules from single-walled carbon nanotubes: synthesis and photophysical properties of short single-walled carbon nanotubes functionalised with 9,10-diphenylanthracene

Carmela Aprile; Roberto Martín; Mercedes Alvaro; Juan C Scaiano; Hermenegildo Garcia

doi:10.1002/chem.200800186

Functional macromolecules from single-walled carbon nanotubes: synthesis and photophysical properties of short single-walled carbon nanotubes functionalised with 9,10-diphenylanthracene

Chemistry. 2008;14(16):5030-8. doi: 10.1002/chem.200800186.

Authors

Carmela Aprile¹, Roberto Martín, Mercedes Alvaro, Juan C Scaiano, Hermenegildo Garcia

Affiliation

¹ Instituto de Tecnología Química CSIC-UPV, Universidad Politécnica de Valencia, Av. de los Naranjos s/n, 46022 Valencia, Spain.

PMID: 18418827
DOI: 10.1002/chem.200800186

Abstract

9,10-Diphenylanthracene (DPA), a well-studied organic chromophore (Phi(fl) = 0.98) that exhibits electroluminescence, has been covalently bound through 2-(ethylthio)ethylamido linkers to the carboxylic acid groups of short, soluble single-walled carbon nanotubes (sSWNTs) of 1 microm average length, and the resulting DPA-functionalised sSWNT (DPA- sSWNT) macromolecular adducts (4.6 wt % DPA content) characterised by solution (1)H NMR, Raman and IR spectroscopy and thermogravimetric analysis. Comparison of the quenching of DPA fluorescence (steady-state and time-resolved) and of the transient optical spectra of sSWNTs and DPA-sSWNTs show that the covalent linkage boosts the interaction between the DPA and the sSWNT units. DPA-sSWNTs exhibit emission in the near-IR region from 1100-1400 nm with an enhanced quantum yield (Phi = 5.7x10(-3)) compared with sSWNTs (Phi = 3.9x10(-3)).