- AutorIn
- Prof. Dr. Junzhi Liu Technische Universität, Fakultät für Chemie und Lebensmittelchemie#Center for Advancing Electronics Dresden (cfaed)
- Dr. Ji MaTechnische Universität Dresden, Fakultät für Chemie und Lebensmittelchemie#Center for Advancing Electronics Dresden (cfaed)
- Ke ZhangMax-Planck Institut für Polymerforschung, Mainz
- Prince Ravat
- Peter Machata
- Stanislav Avdoshenko
- Dr. Felix Hennersdorf
- Hartmut Komber
- Wojciech Pisula
- Prof. Dr. Jan J. Weigand
- Alexey A. Popov
- Dr. Reinhard Berger
- Prof. Klaus Müllen
- Prof. Dr. Xinliang Feng
- Titel
- π-Extended and Curved Antiaromatic Polycyclic Hydrocarbons
- Zitierfähige Url:
- https://nbn-resolving.org/urn:nbn:de:bsz:14-qucosa2-365771
- Quellenangabe
- Journal of the American Chemical Society Erscheinungsort: Washington
Verlag: ACS Publications
Erscheinungsjahr: 2017
Jahrgang: 139
Heft: 22
Seiten: 7513-7521
E-ISSN: 1520-5126 - Erstveröffentlichung
- 2017
- Abstract (EN)
- Synthesis of antiaromatic polycyclic hydrocarbons (PHs) is challenging because the high energy of their highest occupied molecular orbital and low energy of their lowest unoccupied molecular orbital cause them to be reactive and unstable. In this work, two large antiaromatic acene analogues, namely, cyclopenta[pqr]indeno[2,1,7-ijk]tetraphene (CIT, 1a) and cyclopenta[pqr]indeno[7,1,2-cde]picene (CIP, 1b), as well as a curved antiaromatic molecule with 48 πelectrons, dibenzo[a,c]diindeno[7,1,2-fgh:7′,1′,2′-mno]-phenanthro[9,10-k]tetraphene (DPT, 1c), are synthesized on the basis of the corona of indeno[1,2-b]fluorene. These three antiaromatic PHs possess a narrow energy gap down to 1.55 eV and exhibit high kinetic stability under ambient conditions. Moreover, these compounds display reversible electron transfer processes in both the cathodic and anodic regimes. Their cation and anion radicals are characterized by in situ vis−NIR absorption and electron paramagnetic resonance spectroelectrochemistry. The X-ray crystallographic analysis confirms that while CIP and CIT manifest planar structures, DPT shows a curved πconjugated carbon skeleton. The synthetic strategy starting from ortho-substituted benzene units to construct five-membered rings in this work provides a unique entry to novel pentagon-embedding or curved antiaromatic polycyclic hydrocarbons. In addition, besides the detailed chemical and physical investigations, microscale single-crystal fiber field-effect transistors were also fabricated.
- Andere Ausgabe
- Linz zum Artikel, der zuerst in der Zeitschrift 'Journal of the American Chemical Society' erschienen ist.
DOI: 10.1021/jacs.7b01619 - Freie Schlagwörter (DE)
- Antiaromatische polyzyklische Kohlenwasserstoffe, Photovoltaik, HOMO − LUMO-Energielücke
- Freie Schlagwörter (EN)
- Antiaromatic Polycyclic Hydrocarbons, photovoltaics, HOMO−LUMO energy gap
- Klassifikation (DDC)
- 540
- Verlag
- ACS Publications, Washington
- Förder- / Projektangaben
- Europäischer Sozialfonds Horizon2020
Graphenzentrum Dresden (GraphD)
ID: 100270084 - Version / Begutachtungsstatus
- publizierte Version / Verlagsversion
- URN Qucosa
- urn:nbn:de:bsz:14-qucosa2-365771
- Veröffentlichungsdatum Qucosa
- 06.01.2020
- Dokumenttyp
- Artikel
- Sprache des Dokumentes
- Englisch
- Lizenz / Rechtehinweis