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Annulated Azuleno[2,1,8-ija]azulenes: Synthesis and Properties |
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| Authors: | Pierre Mathey Frédéric Lirette Prof. Dr. Israel Fernández Lukas Renn Prof. Dr. R. Thomas Weitz Prof. Dr. Jean-François Morin |
| Affiliation: | 1. Department of Chemistry and Centre de Recherche sur les Matériaux Avancés (CERMA), Université Laval, 1045 Ave de la Medecine, Québec, QC, G1V0A6 Canada These authors contributed equally to this work.;2. Departamento de Química Orgánica and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, Spain;3. 1st Institute of Physics, Faculty of Physics, Georg-August-University, Göttingen, Germany International Center for Advanced Studies of Energy Conversion (ICASEC), University of Göttingen, Göttingen, Germany;4. Department of Chemistry and Centre de Recherche sur les Matériaux Avancés (CERMA), Université Laval, 1045 Ave de la Medecine, Québec, QC, G1V0A6 Canada |
| Abstract: | Non-alternant non-benzenoid hydrocarbons exhibit very different optical and electronic properties than their well-studied benzenoid analogues. However, preparing such structures with extended conjugation length, remains challenging. Herein, we report the synthesis and properties of azuleno[2,1,8-ija]azulene derivatives using a two-step sequence involving a four-fold aldol condensation between aromatic dialdehydes and readily available tetrahydropentalene-2,5-(1H,3H)-dione. Molecules with band gap values ranging from 1.69 to 2.14 eV and molar extinction coefficients (ϵ) of nearly 3×105 M−1 cm−1 have been prepared. These annulene-like structures exhibit significant diatropic ring currents (aromatic), as supported by 1H NMR spectroscopy and DFT calculations. Field-effect transistors (OFETs) using azuleno[2,1,8-ija]azulene derivatives as semiconductors exhibit charge mobility values of up to 0.05 cm2 V−1 s−1. |
| Keywords: | Annulene Aromaticity Azulene Semiconductors π-Conjugated Molecules |