An Approach to Paracyclophane-Based Tetrathiafulvalenes: Synthesis and Characterization of a Pseudo-Geminal [2.2]Paracyclophane 1,3-Dithia-2-Thione

Lucian G Bahrin; Henning Hopf; Peter G Jones; Mihail L Birsa; Laura G Sarbu

doi:10.3390/molecules25225262

An Approach to Paracyclophane-Based Tetrathiafulvalenes: Synthesis and Characterization of a Pseudo-Geminal [2.2]Paracyclophane 1,3-Dithia-2-Thione

Molecules. 2020 Nov 11;25(22):5262. doi: 10.3390/molecules25225262.

Authors

Lucian G Bahrin^{1

2}, Henning Hopf², Peter G Jones³, Mihail L Birsa^{2

4}, Laura G Sarbu^{2

4}

Affiliations

¹ Petru Poni Institute of Macromolecular Chemistry, Intelcenter. 41A Grigore Ghica Vodă Alley, 700487 Iasi, Romania.
² Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
³ Institute of Inorganic and Analytical Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
⁴ Department of Chemistry, Alexandru Ioan Cuza University of Iasi, 11 Carol I Blvd., 700506 Iasi, Romania.

Abstract

The synthesis of paracyclophane-based tetrathiafulvalene precursors is described in the context of the importance of these compounds in the field of material chemistry. Pseudo-geminal bis(1,3-dithia-2-thione) was synthesized via the corresponding 1,3-dithiol-2-ylium salt. The latter was obtained by a synthetic procedure that involves 4,15-bis(acetyl)[2.2]paracyclophane, a new compound of interest for many researchers.

Keywords: 1,3-dithiolium salts; [2.2]paracyclophanes; dithiocarbamates; trithiones.

MeSH terms

Chemistry Techniques, Synthetic / methods*
Crystallography, X-Ray
Heterocyclic Compounds / chemistry*
Magnetic Resonance Spectroscopy
Models, Chemical
Models, Molecular
Molecular Structure
Polycyclic Compounds / chemistry
Stereoisomerism
Thiones / chemistry*

Substances

Heterocyclic Compounds
Polycyclic Compounds
Thiones
tetrathiafulvalene