This report details the synthesis of new NON trianionic pincer ligand precursors and metalation reactions to form group (IV) complexes. N,N'[1,3-phenylenebis(methylene)]bis-2,6-diisopropylaniline [2,6-(PrNCN)-Pr-i]H-3 (8) was converted to the N,N'-substituted Si(IV), Sn(IV), Mg(II), and Zn(II) derivatives. [2,6-(PrNCHN)-Pr-i](SiMe3)(2) (9-Si) and [2,6-(PrNCHN)-Pr-i](SnMe3)(2) (9-Sn) form by first treating 8 with MeLi followed by Me3MCl, where M = Si or Sn. Single crystal X-ray experiments indicate 8, 9-Si, and 9-Sn have similar structural features in the solid state. [2,6-(PrNCHN)-Pr-i](mu-MgCl center dot THF)(2) (12) forms by treating 8 with MeMgCl, and its solid state structure revealed a bis-mu-MgCl bridging unit. The H-1 NMR spectrum of 12 reveals a dynamic process occurs in solution. A variable temperature H-1 NMR experiment failed to quench the dynamic process. {[2,6-(PrNCHN)-Pr-i]Zn}(2) (13) forms upon treating {[2,6-(PrNCHN)-Pr-i]Li-2}(2) (10) with anhydrous ZnCl2 and is a dimer in the solid state. Again, dynamic H-1 NMR behavior is observed, and a mechanism is provided to explain the apparent low symmetry of 13 in solution. Extension of the aliphatic arm of the NON ligand provides the new (NCN)-C-C-N-C pincer ligand precursors N,N'-(2,2'center dot(1,3-phenylene)bis(ethane-2,1-diyl))bis(3,5-bis(trifluoromethyl)anili ne) [3,5-(CF3NCN)-C-C-N-C]H-3 (16) and [3,5-(CF3NCHN)-C-C-N-C](SiMe3)(2) (17). A more rigid ligand architecture was accessed by synthesis of the anthracene derived pincer ligand anthracene-1,8-diylbis(N-3,5-bistrifluormethylaniline) [3,5-(CF3NCanthN)-C-C-N-C]H-3 (18). Treating {Zr(NMe2)(4)}(2) with 2 equiv of 16 provides the dimer {(mu-3,5CF(3)N(C)CH(C)N)Zr(NMe2)(3)NHMe2}(2) (19). Treating Hf(NMe2)(4) with 18 provides the bimetallic complex (mu-3,5-(CF3NCHanthN)-C-C-N-C){Hf(NMe2)(3)NHMe2}(2) (20) in which one ligand bridges two Hf(IV) ions. Salt metathesis between 10 and ZrCl2(NMe2)(2)(THF)(2) provides the mononuclear complex [2,6-(PrNCHN)-Pr-i]Zr(NMe2)(2) (21) in which the NCN ligand is bound as a chelating diamide. Thermoysis of 21 does not lead to formation of a trianionic pincer complex. Instead, treating HfCl4 with {[2,6-(PrNCN)-Pr-i]Li-3}(2) (11) followed by MeLi provides the trianionic pincerate complex [2,6-(PrNCNHfMe2)-Pr-i][Li(DME)(2)] (23). In the solid state the Hf ion has distorted trigonal bipyramidal geometry.