20199-34-2Relevant academic research and scientific papers
Synthesis, characterization, and modeling of naphthyl-terminated sp carbon chains: Dinaphthylpolyynes
Cataldo, Franco,Ravagnan, Luca,Cinquanta, Eugenio,Castelli, Ivano Eligio,Manini, Nicola,Onida, Giovanni,Milani, Paolo
experimental part, p. 14834 - 14841 (2011/03/17)
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).
