Toward an Air-Stable Triradical with Strong Spin Coupling: Synthesis of Substituted Truxene-5,10,15-triyl.

With the aim to achieve air-stable polyradical species manifesting strong spin coupling, synthetic endeavors are made toward triradical molecules featuring a truxene-triyl skeleton. Commonly used steric-hindering side groups such as 2,4,6-trichlorophenyl and 9-anthracenyl are both found to be incompetent at stabilizing the targeted truxene triradical, which appears to be elusive from isolation and characterization. Nonetheless, single-crystal structures of adducts formed by relevant radicals are obtained, which strongly suggests the transient existence of the designed triradicals. Finally, a truxene triradical comprising 1-anthracenyl along with two 9-anthracenyl substituents is successfully isolated and found to exhibit decent stability in air. We propose that because of the smaller dihedral angle assumed by 1-anthracenyl with respect to the plane of truxene-triyl, more effective π-conjugation allows the spin density to be more widely delocalized and distributed to the anthracenyl side groups. Thus, higher stability is gained by the triradical molecule.