Organic Letters
Organic Letters
5 years ago

Isolable Triradical Trication of Hexaaza[16]paracyclophane with Embedded 9,10-Anthrylenes: A Frustrated Three-Spin System

Isolable Triradical Trication of Hexaaza[16]paracyclophane with Embedded 9,10-Anthrylenes: A Frustrated Three-Spin System
Tetsuo Iwanaga, Takashi Matsumoto, Masashi Uebe, Daisuke Sakamaki, Ryohei Kurata, Akihiro Ito, Mariko Kinoshita
A new derivative of hexaaza[16]paracyclophane in which p-phenylenes are alternately replaced by 9,10-anthrylenes was prepared to investigate the impact on overall π-conjugation as well as conformational change of the macrocycle. The charge and spin distribution for one-electron and three-electron oxidation of the macrocycle was elucidated by means of electrochemical, spectroelectrochemical, EPR spectroscopic, and SQUID magnetometric methods. In particular, the triradical trication was successfully isolated as an air-stable salt, and moreover, its structure was disclosed by X-ray analysis. The triradical trication was characterized as a spin-frustrated three-spin system with the antiferromagnetic exchange interaction (J/kB ≃ – 74 K).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02088

DOI: 10.1021/acs.orglett.7b02088

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