TY - JOUR
T1 - Air- and water-stable, fluorescent oligomers of 9,10-dihydro-9,10- diboraanthracene
AU - Reus, Christian
AU - Guo, Fang
AU - John, Alexandra
AU - Winhold, Marcel
AU - Lerner, Hans Wolfram
AU - Jäkle, Frieder
AU - Wagner, Matthias
PY - 2014/6/10
Y1 - 2014/6/10
N2 - Air- and water-stable, -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 systems 80 (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 (f = 47%) and as thin film ( f = 13%).
AB - Air- and water-stable, -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 systems 80 (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 (f = 47%) and as thin film ( f = 13%).
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U2 - 10.1021/ma500518x
DO - 10.1021/ma500518x
M3 - Article
AN - SCOPUS:84902134493
SN - 0024-9297
VL - 47
SP - 3727
EP - 3735
JO - Macromolecules
JF - Macromolecules
IS - 11
ER -