We report the first class of stable, two-dimensional (2D) anti-ferromagnetically coupled dendritic polyradicaloids. A kinetically blocked fluorenyl radical was used to build up the first and second generation dendrons FR-G1 and FR-G2 containing three and seven fluorenyl units, respectively. The neighboring fluorenyl radicals in FR-G1 and FR-G2 show moderate anti-ferromagnetic exchange interaction, resulting in a doublet and quartet ground state, respectively, with a small doublet-quartet energy gap. From FR-G1 to FR-G2, the energy gap decreased and the two-photon absorption was enhanced owing to more extended 2D π-conjugation. Both compounds showed multiple redox waves due to their polyradical character.
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