Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 5, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202104245
Keywords
pi-clusters; anthracene; CH-pi interactions; excited-state dynamics; photoisomerization
Categories
Funding
- JSPS KAKENHI [JP17K17849, JP20K05475, JP21H05395, JP21H01888]
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This study reported the synthesis of 1,2,3-tri(9-anthryl)benzene derivatives with unique electronic properties via Negishi coupling. In the crystalline state, interactions between anthracene units facilitated the formation of a two-dimensional packing structure. Understanding the excited-state dynamic behavior revealed insights into exciton localization/delocalization processes.
We report the Negishi coupling based synthesis of 1,2,3-tri(9-anthryl)benzene derivatives containing three radially arranged anthracenes in a pi-cluster. In the crystalline state of the unsubstituted derivative, intermolecular pi-pi and CH-pi interactions between the anthracene units drive the formation of the two-dimensional packing structure. Owing to though-space pi-conjugation between anthracene units, the substances have unique electronic properties. The excited-state dynamic behavior occurring between the three anthracene moieties, such as exciton localization/delocalization, was elucidated by means of transient absorption measurements and quantum chemical calculations. Interestingly, even though the three anthracenes are closely oriented with approximately 3.0 angstrom between their C-9 positions, exciton localization on two anthracene units is energetically favorable because of the flexible nature of the radially arranged aromatic rings.
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