Molecular and Spin Structures of a Through-Space Conjugated Triradical System.

A through-space conjugated multi-phenalenyl triradical 1 a has been prepared and characterized. Partial occupancy of doubly degenerate molecular orbitals in 1 a leads to Jahn-Teller distortion, creating a molecular skeleton in which C2v doublet states are lower in energy than undistorted D3h doublet and quartet states. Triradical 1 a exists in an acute form in the solution state, whereas it adopts a preferred obtuse form in the solid state. The results of the investigation show that these two distorted forms are reversibly interconverted by thermal energy.

A facile synthesis of trinaphtho[3.3.3]propellane and its π-extension and the formation of a two-dimensional honeycomb molecular assembly.

The multi-gram-scale synthesis of trinaphtho[3.3.3]propellane (TNP) and its π-extension were achieved. X-ray crystallographic analysis revealed that charge transfer complexes of the π-extended TNP with F4-TCNQ form a two-dimensional honeycomb lattice.