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Synthesis,solid-state photophysical properties and electropolymerization of novel diazulenyl ethenes
Authors:Eugenia Andreea Dragu  Simona Nica  Matei Raicopol  Adriana Baran  Dan-Florin Anghel  Bogdan Cojocaru  Laszlo Tarko  Alexandru C. Razus
Affiliation:1. Institute of Organic Chemistry, ‘C.D. Nenitzescu’ of Romanian Academy, 202 B Splaiul Independentei, Bucharest 060023, Romania;2. ‘Petru Poni’ Institute of Macromolecular Chemistry of Romanian Academy, 41 A, Grigore-Ghica Voda Alley, Iasi 700847, Romania;3. University ‘Politehnica’ of Bucharest, Faculty of Applied Chemistry and Materials Science, ‘C.D. Nenitzescu’ Organic Chemistry Department, 1-7 Polizu, Bucharest 011061, Romania;4. ‘Ilie Murgulescu’ Institute of Physical Chemistry of Romanian Academy, Department of Colloidal Chemistry, 202 Splaiul Independentei, Bucharest 060021, Romania;5. University of Bucharest, Faculty of Chemistry, Department of Chemical Technology and Catalysis, Bd. Regina Elisabeta 4-12, Bucharest 030016, Romania
Abstract:The novel 1,2-di(azulen-1-yl)cyclopent-1-ene 3 was conveniently synthesized via a two-step procedure involving Vilsmeier–Haack acylation of azulene with N,N,N′,N′-tetraethylglutaramide (TEGA) and POCl3, followed by an intramolecular McMurry coupling of the resulting diketone. In contrast with the previously reported (E)-1,2-di(azulen-1-yl)ethene that shows negligible fluorescence in the solid state, alkene 3 displays fluorescence emission from the S2 excited state of the azulene moieties. This compound easily polymerizes upon electrochemical oxidation, leading to the formation of a conducting polymer film at the electrode surface.
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