A new TTF donor covalently appended with a 1,5-diisopropylverdazyl radical via a cross-conjugated pyridyl linker 3 has been prepared and characterized. Reaction of 3 with TCNQ afforded the 2:1 charge transfer complex, (3)2TCNQ (4) where the IR and structural data are consistent with 0.25 e- charge transfer from the TTF donor to the TCNQ acceptor. The TTF and TCNQ molecules adopt a mixed-stack D-D-A arrangement that does not facilitate conduction.A solution EPR spectrum of 4 comprises a broad featureless singlet, consistent with the presence of a TCNQ radical anion. Theoretical studies were carried out to probe the exchange interactions within selected fragments of 4, with and without charge transfer; In the absence of charge transfer, DFT calculations reveal weak antiferromagnetic exchange between verdazyl radicals within the (3)2 monoradical unit. However, partial oxidation of the dimer (3)2 to the diradical cation leads to an S = ½ ground state in which the verdazyl radical spins are now switched to co-parallel as a consequence of antiferromagnetic exchange to the additional delocalised TTF-based spin containing unit. The magnetic properties of 4 are consistent with a net S = ½ spin state per formula unit with dominant antiferromagnetic interactions between spin-bearing building blocks.