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C‐Halogenated 9,10‐Diboraanthracenes: How the Halogen Load and Distribution Influences Key Optoelectronic Properties
Author(s) -
Brend'amour Simon,
Gilmer Jannik,
Bolte Michael,
Lerner HansWolfram,
Wagner Matthias
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804288
Subject(s) - homo/lumo , halogen , bathochromic shift , photochemistry , quantum yield , chemistry , fluorescence , absorption (acoustics) , electroluminescence , band gap , materials science , molecule , optoelectronics , organic chemistry , physics , alkyl , optics , layer (electronics) , composite material
9,10‐Dihydro‐9,10‐diboraanthracenes (DBAs) have low‐energy LUMOs and narrow HOMO–LUMO gaps and are thus attractive electron‐transporting and light‐emitting materials in optoelectronic devices. A systematic series of ten C‐halogenated 9,10‐(Mes) 2 ‐DBAs was synthesized and studied by cyclic voltammetry, UV/Vis absorption and emission spectroscopy, and quantum‐chemical calculations (Mes=mesityl). We probed the influence of the nature of the halogen atoms and the halogen substitution patterns on key optoelectronic properties of the DBAs. All 9,10‐(Mes) 2 derivatives can be reversibly reduced at the DBA cores and at electrode potentials between E 1/2 Red1 =−1.84 and −1.26 V (vs. FcH/FcH + ). The most bathochromic UV/Vis absorption and the fluorescence emission of each DBA correspond to an ICT transition between the Mes rings and the DBA core. Br substituents lower the DBA LUMO energy and narrow the energy gap to the highest degree along the series F