Synthesis, Characterization, and Modeling of Naphthyl-Terminated sp Carbon Chains: Dinaphthylpolyynes

Franco Cataldo, Luca Ravagnan, Eugenio Cinquanta, Ivano Eligio Castelli, Nicola Manini, Giovanni Onida, Paolo Milani

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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).
Original languageEnglish
JournalJournal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical
Volume114
Issue number46
Pages (from-to)14834-14841
ISSN1520-6106
DOIs
Publication statusPublished - 2010
Externally publishedYes

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