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)
Highlights
Polyphenylenes or hexaarylbenzene derivatives (I) are of considerable interest as they are the precursors for polycyclic aromatic hydrocarbons (Watson et al 2001)
Scheme 1 Synthesis of ligands (2) and molybdenum complexes (3), and atom labelling used for the assignment of NMR data
First we studied the coordination chemistry of these two ligands with zerovalent molybdenum centres stabilised by carbonyl ligands
Summary
Polyphenylenes or hexaarylbenzene derivatives (I) are of considerable interest as they are the precursors for polycyclic aromatic hydrocarbons (Watson et al 2001). A few years ago we reported the synthesis of N-heterosuperbenzene (N-HSB) (II) by cyclodehydrogenation of the precursor (III) (Draper et al 2002). We reported the synthesis of a pyridyl-centred polyphenylene (IV) and its coordination chemistry, with rhodium and palladium (Ollagnier et al 2008). The presence of a fused 5-membered ring in the skeleton makes fluoranthene derivatives suitable for the preparation of curved molecules such as corannulene and semibuckminsterfullerene (Sygula & Rabidean, 1999). Fluoranthene derivatives can be cyclodehydrogenated to generate large aromatic sheets (Debad et al 1996 & Wehmeier et al 2001).
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