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Issue 21, 2017
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4N electron aromatic cycles in polycyclic hydrocarbons

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Polycyclic fully conjugated hydrocarbons in which aromatics are fused to aromatics – or aromatics to antiaromatics – are important as potential organic semiconductors. Herein we explore the only remaining fusion pattern of antiaromatics to antiaromatics. It is shown computationally that the central antiaromatic unit (cyclobutadiene or pentalene) in such a three-unit polycyclic hydrocarbon, generated by fusion of three antiaromatic molecules, turns aromatic according to magnetic shielding (NICS) criteria. The resulting neutral 4N electron molecules possess a 4N π electron perimeter with pronounced CC bond length equalization (as indicated by the HOMA geometric index) and significant aromatic stabilization energies (computed using the isomerization-stabilization method) and could be promising synthetic targets with small HOMO–LUMO gaps.

Graphical abstract: 4N electron aromatic cycles in polycyclic hydrocarbons

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The article was received on 09 Apr 2017, accepted on 04 May 2017 and first published on 18 May 2017

Article type: Paper
DOI: 10.1039/C7CP02288C
Citation: Phys. Chem. Chem. Phys., 2017,19, 14066-14072
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    4N electron aromatic cycles in polycyclic hydrocarbons

    M. Mauksch and S. B. Tsogoeva, Phys. Chem. Chem. Phys., 2017, 19, 14066
    DOI: 10.1039/C7CP02288C

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