Abstract

The six-membered cyclic 1,4-radical cation 2•+ forms a “twisted π-space” due to noncoplanarity of the cumyl radical 3• and cumyl cation 3+ originating from a chair conformation of the central cyclohexane ring system. The results of substituent effects on absorption wavelengths of 2•+ indicate that both through-space (TS) and through-bond (TB) orbital interactions operate in a “twisted π-space” of 2•+, resulting in the theoretically maximal orbital interactions between 3• and 3+. An operation of similar TS and TB orbital interactions is also suggested in the excited-state biradical 12••* by the results of substituent effects on thermoluminescence wavelengths.

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