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10) has been synthesized [161a]. Both hexaphenyl- and tetraphenyl-carbo-benzenes fulfill the criteria of aromatic structures: they are stable, diatropic (deshielded 1H NMR chemical shifts), with a quasi D6h central ring (according to X-ray crystal structures). These experimental data served as references for following theoretical investigations. 3 x Structural criterion. 10). 369 â) [127,162]. In contrast, HF  or AM1 calculations  failed to reproduce the D6h symmetry. 10 Experimentally determined (X-ray) and calculated (B3PW91/6-31G*) structures of tetraphenyl carbo-benzene.
Push-pull chromophores involving carbo-phenylene units were investigated for possible first-order NLO properties. At the ZINDO level, the static quadratic hyperpolarizability of the full carbo-mer of p-nitroaniline (b0 = 841 q 10 –30 cm5 esu–1) is 80 times greater than that of p-nitroaniline (b0 = 10 q 10 –30 cm5 esu–1) . 16) still exhibit a promising b0 exaltation: b0(X = NH2) = 810 q 10 –30 cm5 esu–1, b0(X = H) = 633 q 10 –30 cm5 esu–1. However, carbo-merization of the acceptor NO2 group remains essential.
The “electronic” aromaticity criterion is based on the ELF analysis of r(r) . 2), carbo-annulenes possess a cyclically homoconjugated in-plane pxy MO system, and the ELF tool allows for a relative weighting of resonance forms associated with in-plane and outof-plane cyclic delocalization . The aromaticity of the ring carbo-mers of the first annulenes was theoretically investigated according to these four criteria. The process is detailed first for carbo-benzene (C18H6), which was proposed as a synthetic challenge in 1995 .