- AutorIn
- Jason Melidonie Technische Universitat Dresden, Fakultät für Chemie und Lebensmittelchemie#Center for Advancing Electronics Dresden (cfaed)
- Dr. Junzhi LiuTechnische Universitat Dresden, Fakultät für Chemie und Lebensmittelchemie#Center for Advancing Electronics Dresden (cfaed)
- Yubin FuTechnische Universitat Dresden, Fakultät für Chemie und Lebensmittelchemie#Center for Advancing Electronics Dresden (cfaed)
- Prof. Dr. Jan J. Weigand
- Dr. Reinhard Berger
- Prof. Dr. Xinliang Feng
- Titel
- Pyrene-Fused s-Indacene
- Zitierfähige Url:
- https://nbn-resolving.org/urn:nbn:de:bsz:14-qucosa2-365766
- Quellenangabe
- The journal of Organic Chemistry Herausgeber: J. Org. Chem
Erscheinungsort: Washington
Verlag: American Chemical Society
Erscheinungsjahr: 2018
Jahrgang: 83
Heft: 12
Seiten: 6633-6639
E-ISSN: 1520-6904 - Erstveröffentlichung
- 2018
- Abstract (EN)
- One antiaromatic polycyclic hydrocarbon (PH) with and without solubilizing tert-butyl substituents, namely s-indaceno[2,1-a:6,5-a′]dipyrene (IDPs), has been synthesized by a four-step protocol. The IDPs represent the longitudinal, peri-extension of the indeno[1,2-b]fluorene skeleton towards a planar 40 π-electron system. Their structures were unambiguously confirmed by X-ray crystallographic analysis. The optoelectronic properties were studied by UV/vis absorption spectroscopy and cyclic voltammetry. These studies revealed that peri-fusion renders the IDP derivatives with a narrow optical energy gap of 1.8 eV. The maximum absorption of IDPs is shifted by 160 nm compared to the parent indenofluorene. Two quasi-reversible oxidation as well as reduction steps indicate an excellent redox behavior attributed to the antiaromatic core. Formation of the radical cation and the dication was monitored by UV/vis absorption spectroscopy during titration experiments. Notably, the fusion of s-indacene with two pyrene moieties lead to IDPs with absorption maxima approaching the near infrared (NIR) regime.
- Andere Ausgabe
- Link: Link zum Artikel, der zuerst in der Zeitschrift 'The Journal of Organic Chemistry' erschienen ist.
DOI: 10.1021/acs.joc.8b00925 - Forschungsdatenverweis
- Pyrene-Fused s‑Indacene
DOI: doi.org/10.1021/acs.joc.8b00925
Link: https://pubs.acs.org/doi/10.1021/acs.joc.8b00925 - Freie Schlagwörter (DE)
- antiaromatische polycyclische Kohlenwasserstoffe, optoelektronische Eigenschaften
- Freie Schlagwörter (EN)
- antiaromatic polycyclic hydrocarbon, optoelectronic properties
- Klassifikation (DDC)
- 540
- 610
- 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-qucosa2-365766
- Veröffentlichungsdatum Qucosa
- 06.01.2020
- Dokumenttyp
- Artikel
- Sprache des Dokumentes
- Englisch
- Lizenz / Rechtehinweis