TY - JOUR
T1 - Synthesis, Characterization, and Modeling of Naphthyl-Terminated sp Carbon Chains
T2 - Dinaphthylpolyynes
AU - Cataldo, Franco
AU - Ravagnan, Luca
AU - Cinquanta, Eugenio
AU - Castelli, Ivano Eligio
AU - Manini, Nicola
AU - Onida, Giovanni
AU - Milani, Paolo
PY - 2010
Y1 - 2010
N2 - We report a combined study on the synthesis, spectroscopic characterization, and theoretical modeling of a series of α,ω-dinaphthylpolyynes. We synthesized this family of naphthyl-terminated sp carbon chains by reacting diiodoacetylene and 1-ethynylnaphthalene under the Cadiot−Chodkiewicz reaction conditions. By means of liquid chromatography (HPLC), we separated the products and recorded their electronic absorption spectra, which enabled us to identify the complete series of dinaphthylpolyynes Ar−C2n−Ar (with Ar = naphthyl group and n = number of acetilenic units) with n ranging from 2 to 6. The longest wavelength transition (LWT) in the electronic spectra of the dinaphthylpolyynes red shifts linearly with n away from the LWT of the bare termination. This result is also supported by DFT-LDA simulations. Finally, we probed the stability of the dinaphthylpolyynes in a solid-state precipitate by Fourier-transform infrared spectroscopy and by differential scanning calorimetry (DSC).
AB - We report a combined study on the synthesis, spectroscopic characterization, and theoretical modeling of a series of α,ω-dinaphthylpolyynes. We synthesized this family of naphthyl-terminated sp carbon chains by reacting diiodoacetylene and 1-ethynylnaphthalene under the Cadiot−Chodkiewicz reaction conditions. By means of liquid chromatography (HPLC), we separated the products and recorded their electronic absorption spectra, which enabled us to identify the complete series of dinaphthylpolyynes Ar−C2n−Ar (with Ar = naphthyl group and n = number of acetilenic units) with n ranging from 2 to 6. The longest wavelength transition (LWT) in the electronic spectra of the dinaphthylpolyynes red shifts linearly with n away from the LWT of the bare termination. This result is also supported by DFT-LDA simulations. Finally, we probed the stability of the dinaphthylpolyynes in a solid-state precipitate by Fourier-transform infrared spectroscopy and by differential scanning calorimetry (DSC).
U2 - 10.1021/jp104863v
DO - 10.1021/jp104863v
M3 - Journal article
C2 - 20973472
VL - 114
SP - 14834
EP - 14841
JO - Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical
JF - Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical
SN - 1520-6106
IS - 46
ER -