Bidirectional Synthesis of a Unilaterally Substituted Fluorotetracene
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The synthesis of a new 1,10,11,12-tetrafluorotetracene with a C2-symmetry has been successfully achieved. Compared to 1,2,9,10,11-pentafluorotetracene, 1,2,10,12-tetrafluorotetracene and 1,2,12-trifluorotetracene, which were synthesize via a convergent route, the synthesis of the new 1,10,11, 12-tetrafluorotetracene was achieved via a bidirectional synthesis route. This allows simultaneous functionalization of both sides of the naphthalene derivative as the starting material and halves the number of steps required to synthesize the target molecule. The preparation of 1,10,11,12-tetrafluorotetracene was accomplished after overcoming three main challenges, namely the attachment of a lower side chain with a terminal alkene to the naphthalene derivative, followed by the introduction of the first two fluorine substituents, and finally the attachment of the upper side chain containing a fluoroalkene. After isolating the novel tetrafluorotetracene, it was characterised using NMR spectroscopy and cyclic voltammetry to determine its electrochemical data, as well as UV-Vis spectroscopy and fluorescence spectroscopy.
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