Synthesis of dibenzothiophene, dibenzofuran and carbazole donor-acceptor chromophores

TY - JOUR

T1 - Synthesis of dibenzothiophene, dibenzofuran and carbazole donor-acceptor chromophores

AU - Jepsen, Tue Heesgaard

AU - Larsen, Mogens

AU - Jørgensen, Morten

AU - Nielsen, Mogens Brøndsted

PY - 2013

Y1 - 2013

N2 - We present efficient synthetic protocols for functionalizing dibenzothiophene, dibenzofuran, and carbazole with hydroxy and nitro or cyano groups. The synthesis of these donor-acceptor chromophores is based on a key Suzuki-Miyaura coupling using an appropriately substituted aromatic boronic acid. Subsequent intramolecular SNAr reaction allows formation of the dibenzothiophene and dibenzofuran scaffolds, while a carbon-hydrogen activation reaction is employed to afford the carbazole. A final demethylation step unmasks the phenol moiety of the tricyclic chromophores. The UV/Vis absorption properties of the phenol and phenolate forms of these chromophores are also studied.

AB - We present efficient synthetic protocols for functionalizing dibenzothiophene, dibenzofuran, and carbazole with hydroxy and nitro or cyano groups. The synthesis of these donor-acceptor chromophores is based on a key Suzuki-Miyaura coupling using an appropriately substituted aromatic boronic acid. Subsequent intramolecular SNAr reaction allows formation of the dibenzothiophene and dibenzofuran scaffolds, while a carbon-hydrogen activation reaction is employed to afford the carbazole. A final demethylation step unmasks the phenol moiety of the tricyclic chromophores. The UV/Vis absorption properties of the phenol and phenolate forms of these chromophores are also studied.

U2 - 10.1055/s-0032-1318484

DO - 10.1055/s-0032-1318484

M3 - Journal article

SN - 0039-7881

VL - 45

SP - 1115

EP - 1120

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 8

ER -