期刊
JOURNAL OF PHYSICAL CHEMISTRY B
卷 114, 期 46, 页码 14834-14841出版社
AMER CHEMICAL SOC
DOI: 10.1021/jp104863v
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资金
- Italian Space Agency [1/015/07/0]
- European Union [211956, 164]
We report a combined study on the synthesis, spectroscopic characterization, and theoretical modeling of a series of alpha,omega-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-C(2n)-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).
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