Protective group synthesis of poly-N-hydro-(3,6-carbazolyl)

Autor: Stephen T. Wellinghoff, Joel R. Racchini, Samson A. Jenekhe
Rok vydání: 1988
Předmět:
Zdroj: Synthetic Metals. 22:291-303
ISSN: 0379-6779
DOI: 10.1016/0379-6779(88)90102-6
Popis: Poly-N-trityl-(3,6-carbazolyl), PNTPMCZ, has been synthesized in pyridine solution using an activated nickel catalyst. 9-Trityl-3,6-diiodocarbazole was polymerized and the triphenylmethyl group subsequently removed by acid hydrolysis. The N-protected monomer was made by a phase-transfer reaction employing 3,6-diiodocarbazole, a benzotriethylammonium chloride catalyst, basic solution and triphenylmethyl chloride. A wide variety of N-substituents can be obtained in this way, allowing the molecular design of polycarbazolyls to be controlled. In addition, weakly-bound N-substituents can be employed for solubility enhancement during reaction and subsequently partially or fully cleaved from the polymer by acid hydrolysis. Poly-N-hydro-(3,6-carbazolyl), PNHCZ, obtained from PNTPMCZ, forms iodine complexes with conductivities of 10−1 ohm−1 cm−1 at room temperature. The visible-near-i.r. spectra suggest that the same radical cations responsible for conductivity in poly-N-methyl-(3,6-carbazolyl) are present. Direct comparisons of the structure and physical properties of PTPMCICZ (a predominantly poly-N-hydro-(3,6-carbazolyl) synthesized in liquid iodine) are made.
Databáze: OpenAIRE