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Synthesis and coordination chemistry of N-doped polyphenylenes

Authors:

SD Perera ,

Open University of Sri Lanka, LK
About SD

Professor S.D. Perera is attached to the Department of Chemistry of the Open University of Sri Lanka. His research interests are in the fields of inorganic and organometallic chemistry including transition metal catalysis. Since 2005, he has been involved in research collaboration with Professor Sylvia Draper to develop synthetic routes to novel polycyclic aromatic hydrocarbons.

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R Quesada,

ES
About R
Dr. R. Quesada was a Postdoctoral Research Fellow at Trinity College Dublin and now he is a Lecturer in Chemistry at the University of Burgos, Spain.
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SM Draper

IE
About SM

Professor S.M. Draper is the Head of Inorganic and Synthetic Materials Chemistry at Trinity College of the University of Dublin. Her Research group investigates optical, electrochemical and physical properties of novel N- and S-doped graphenes and advanced materials.

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Abstract

The N-doped polyphenylene derivatives are expected to show interesting optical, electrochemical and structural properties. 8-Azafluoranthene ligands (2a) and (2b) were prepared by a Diels-Alder cycloaddition reaction between 2-cyanopyridine and the  corresponding cyclopentadienone. Treatment of [Mo(CO)4(piperidine)2] with ligands (2) gave the  tetracarbonylmolybdenum(0) complexes [Mo(CO)4(2)] (3), in which the  ligand is coordinated to the  metal through both nitrogen donors. Treatment of (2b) with [Pd(OAc)2] gave the  cyclometallated Pd(II) complex [Pd(OAc)(L)] (4a), in which L is an anionic terdentate-ligand. Treatment of (2b) with [PdCl2(NCPh)2] gave the  complex [PdCl(L)] (4b). The  acetate group of (4a) can be easily replaced by halide ions to give [PdCl(L)] (4b), [PdBr(L)] (4c) and [PdI(L)] (4d), respectively. Treatment of (4a) with DMAP and PPh3 in dichloromethane and the  subsequent addition of NH4PF6  in methanol gave the  corresponding salts [Pd(DMAP)(L)]PF6  (6a) and [Pd(PPh3)(L)]PF6 (6b), respectively.

DOI: http://dx.doi.org/10.4038/ouslj.v6i0.4114

OUSL Journal (2010) Vol. 6, (pp. 59- 74)

Keywords: Polyphenylenes 
How to Cite: Perera, S., Quesada, R. & Draper, S., (2010). Synthesis and coordination chemistry of N-doped polyphenylenes. OUSL Journal. 6, pp.59–74. DOI: http://doi.org/10.4038/ouslj.v6i0.4114
Published on 25 Feb 2010.
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