Journal article
Synthesis, Characterization, and Modeling of Naphthyl-Terminated sp Carbon Chains: Dinaphthylpolyynes
Actinium Chemical Research, Via Casilina 1626/A, I-00133 Rome, Italy, Istituto Nazionale di Astrofisica. Osservatorio Astrofisica di Catania, Via S. Sofia 78, I-95123 Catania, Italy, Dipartimento di Fisica, Università degli Studi di Milano, Via Celoria 16, I-20133 Milano, Italy, CIMAINA, Via Celoria 16, I-20133 Milano, Italy, Dipartimento di Scienza dei Materiali, Università degli Studi di Milano Bicocca, Via Cozzi 53, I-20125 Milano, Italy, and European Theoretical Spectroscopy Facility (ETSF), Via Celoria 16, 20133 Milano, Italy
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).
| Language: | English |
|---|---|
| Publisher: | American Chemical Society |
| Year: | 2010 |
| Pages: | 14834-14841 |
| ISSN: | 15205207 and 15206106 |
| Types: | Journal article |
| DOI: | 10.1021/jp104863v |
