New two-step synthesis of N-(2-ethylhexyl)-2,7-diiodocarbazole as a monomer for conjugated polymers

0382706 - ÚMCH 2013 RIV NL eng J - Journal Article
Výprachtický, Drahomír - Kmínek, Ivan - Pokorná, Veronika - Kaňková, Dana - Cimrová, Věra
New two-step synthesis of N-(2-ethylhexyl)-2,7-diiodocarbazole as a monomer for conjugated polymers.
Designed Monomers and Polymers. Roč. 16, č. 1 (2013), s. 31-37. ISSN 1385-772X. E-ISSN 1568-5551
R&D Projects: GA MŠMT(CZ) 1M06031; GA ČR GAP106/12/0827
Institutional research plan: CEZ:AV0Z40500505
Institutional support: RVO:61389013
Keywords : monomer synthesis * carbazole * ring closure
Subject RIV: BM - Solid Matter Physics ; Magnetism
Impact factor: 2.210, year: 2013

A reasonably efficient two-step synthesis of N-(2-ethylhexyl)-2,7-diiodocarbazole is presented. In the first step, the 4,4′-diiodobiphenyl was nitrated to a mixture of 4,4′-diiodo-2-nitrobiphenyl and 4-iodo-4′-nitrobiphenyl. In the second step, the mixture of these compounds was converted by simultaneous carbazole ring closure and N-alkylation to the N-(2-ethylhexyl)-2,7-diiodocarbazole by means of tris(2-ethylhexyl) phosphite. The synthesis represents a shorter alternative to the known more tedious procedures. The prepared compound is a suitable monomer for synthesis of conjugated polymers for optoelectronic applications.
Permanent Link: http://hdl.handle.net/11104/0212850