Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap
Literature Information
Publication Date
2016-09-27
DOI
10.1039/C6QO00487C
Impact Factor
5.281
Authors
D. C. Grenz, G. Schnakenburg, B. Esser
View Original
Abstract
Dibenzo[a,e]pentalene (DBP) is a low-bandgap organic semiconductor. A versatile synthetic route to DBPs substituted with aryl or alkyl groups in the 5,10-positions and electron-donating or -accepting functionalities in the 2,7-positions is described. Six donor- or acceptor-functionalized DBP derivatives were synthesized that show amphoteric redox behavior and band gaps around 2 eV. Through choice of the 2,7-substituents, the HOMO/LUMO energy levels and band gaps can be adjusted within a range of up to 0.6 eV. In the solid state, the DBP derivatives assume herringbone-type packing structures.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
5,10,15,20-tetrakis(4-boronic acid pinacol ester phenyl) porphyrin
CAS Number:
1332748-00-1
Molecular Formula:
C68H74B4N4O8
![6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid structure](https://static.chemtradehub.com/structs/136/1369160-12-2-6524.webp "6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid structure")
6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid
CAS Number:
1369160-12-2
Molecular Formula:
C7H8N2O2
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