Magnetic Phase Transition in a Heteromolecular Hydrogen-Bonded Complex of Nitronylnitroxide Radicals

An organic molecular acid−base complex has been synthesized from pyridine-substituted biradical 2 in a triplet (S = 1) ground state and a benzoic acid derivative of monoradical 3 with S = 1/2. The two constituent molecules are bound by an OH−N hydrogen bond in a crystalline solid state. The complex has been found to exhibit an antiferromagnetic phase transition at 5 K. The complex is the first example of a hydrogen-bonded heterospin, heteromolecular complex exhibiting a magnetic phase transition in purely organic molecule-based materials.