TY - JOUR
T1 - Conjugated oligomers with alternating heterocycles from a single monomer
T2 - synthesis and demonstration of electroluminescence
AU - Urrego-Riveros, Sara
AU - Bremer, Matthias
AU - Hoffmann, Jonas
AU - Heitmann, Anne
AU - Reynaldo, Thibault
AU - Buhl, Janek
AU - Gates, Paul J
AU - Sönnichsen, Frank
AU - Hissler, Muriel
AU - Gerken, Martina
AU - Staubitz, Anne
PY - 2019/9/17
Y1 - 2019/9/17
N2 - Conjugated oligomers based on two different heterocycles are typically prepared by step growth polycondensation cross-coupling methods from two monomers X-Cycle1-X and M-Cycle2-M with no control of the regioselectivity. In this work, we used a new synthetic strategy that involves an extremely chemoselective reaction of a dielectrophilic compound, X1-Cycle1-X2, with a dinucleophilic component, M1-Cycle2-M2, under Stille conditions. The resulting monomers, X1-Cycle1-Cycle2-M2 are di-heterocyclic push pull monomers that still contain a nucleophilic site (boronic acid) and electrophilic site (bromide) and are set up for a controlled polymerization under Suzuki conditions. In this way, two semiconducting oligomers, based on thiophene/benzene and thiophene/pyridine motifs were synthesized. Both oligomers were characterized in terms of their thermal, electrochemical, absorption, emission and electroluminescence properties
AB - Conjugated oligomers based on two different heterocycles are typically prepared by step growth polycondensation cross-coupling methods from two monomers X-Cycle1-X and M-Cycle2-M with no control of the regioselectivity. In this work, we used a new synthetic strategy that involves an extremely chemoselective reaction of a dielectrophilic compound, X1-Cycle1-X2, with a dinucleophilic component, M1-Cycle2-M2, under Stille conditions. The resulting monomers, X1-Cycle1-Cycle2-M2 are di-heterocyclic push pull monomers that still contain a nucleophilic site (boronic acid) and electrophilic site (bromide) and are set up for a controlled polymerization under Suzuki conditions. In this way, two semiconducting oligomers, based on thiophene/benzene and thiophene/pyridine motifs were synthesized. Both oligomers were characterized in terms of their thermal, electrochemical, absorption, emission and electroluminescence properties
U2 - 10.1039/c9qo00947g
DO - 10.1039/c9qo00947g
M3 - Article (Academic Journal)
SN - 2052-4129
JO - Organic Chemistry Frontiers
JF - Organic Chemistry Frontiers
ER -