Title
Air- and Water-Stable, Fluorescent Oligomers of 9,10-Dihydro-9,10-diboraanthracene
Author
Christian Reus, Fang Guo, Alexandra John, Marcel Winhold, Hans-Wolfram Lerner, Frieder Jäkle, Matthias Wagner
Year
2014
Journal
Macromolecules
Abstract
Air- and water-stable, π-conjugated [−donor–acceptor−]n oligomers containing thiophene fragments as donors and 9,10-dimesityl-9,10-dihydro-9,10-diboraanthracene (DBA(Mes)2) as acceptor units were prepared through Stille-type C–C-coupling protocols. The reaction between 2,6-dibromo-DBA(Mes)2 (1), 2,7-dibromo-DBA(Mes)2 (2), 2-bromo-6,7-dimethyl-DBA(Mes)2 (3), and 2,5-bis(trimethylstannyl)thiophene (7) furnished monodisperse, short-chain model systems80 (2 × DBA(Mes)2, 1 × 2,5-thienylene) and 81 (3 × DBA(Mes)2, 2 × 2,5-thienylene) after GPC separation. In the absence of 3, the oligomerization of 1/2 with 7 provided analogous longer chain macromolecules 9 (MALDI–MS reveals up to 7 repeating units; GPC indicates also significantly longer chains). UV/vis absorption spectroscopy suggests that the obtained chain lengths of 9 are already sufficient to reach the maximum effective conjugation length (the lower limit of the HOMO–LUMO band gap corresponds to 2.3 eV). 9 gives rise to a dark orange fluorescence, both in C6H6 solution (ϕf = 47%) and as thin film (ϕf = 13%).
Full Article
Instrument
FP-8300
Keywords
Fluorescence, Materials