737756-10-4Relevant academic research and scientific papers
Graphitic molecules with partial "Zig/Zag" periphery
Wang, Zhaohui,Tomovic, Zeljko,Kastler, Marcel,Pretsch, Ramona,Negri, Fabrizia,Enkelmann, Volker,Muellen, Klaus
, p. 7794 - 7795 (2004)
A new synthetic protocol that affords novel hexa-peri-hexabenzocoronene (HBC) derivatives with partial "zig/zag" periphery and dramatically different electronic properties has been developed, which represents an important step toward understanding structu
Electron-deficient N-heteroaromatic linkers for the elaboration of large, soluble polycyclic aromatic hydrocarbons and their use in the synthesis of some very large transition metal complexes
Fogel, Yulia,Kastler, Marcel,Wang, Zhaohui,Andrienko, Denis,Bodwell, Graham J.,Muellen, Klaus
, p. 11743 - 11749 (2007)
The selective oxidation of the perimeter of an extended polycyclic aromatic hydrocarbon (PAH), namely a six-fold tert-butylated tetrabenzo[bc,ef,hi,uv] ovalene, led to the formation of an α-diketone. The newly installed carbonyl centers allowed this building block to be converted into the largest known heteroatom-containing PAHs (up to 224 atoms in the aromatic core) by way of the quinoxaline ring condensation reaction. The tert-butyl substituents caused a distortion of the usually planar aromatic frameworks, which hampered the aggregation tendency of the extended aromatic π-systems and led to extraordinarily high solubilities. All of the systems described here, even the giant phthalocyanine, could thus be purified using standard chromatographic techniques and characterized using typical spectroscopic methods. For the first time, fully resolved 1H NMR spectra of soluble, diamagnetic, 98- and 104-atom-containing aromatic systems are presented. The computed and experimental UV/vis spectra emphasize the dependence of the characteristic α-, p-, and β-bands upon the size of the PAHs. It was also possible to obtain the largest known ligand to yet be complexed around a ruthenium center. A quadrupolar solvatochromic effect was observed when two donating PAH moieties were fused to an accepting quinoxaline center, in which case the photoluminescence spanned a range of about 80 nm. Electrochemical properties of the new nanographenes were investigated using cyclic voltammetry, and this showed quasi-reversible reductions.
