Abstract
To further explore anthracene derivatives with bulky 9,10-substituents and a bent molecular skeleton due to repulsive interactions with adjacent ring hydrogens, we have synthesized 9,10-bis(diisopropylsilyl)anthracene and determined its molecular structure. Reduction with lithium metal in THF solution under aprotic conditions and argon yields its radical anion, which has been characterized by its ESR and ENDOR signal patterns. Crystallization from the red THF solution following addition of an n-hexane layer yielded the radical anion as blue, air- and moisture-sensitive needles. Its structure, determined at 130 K in an N 2 flow, is discussed by comparison with that of the neutral molecule and those of 9,10-bis(trimethylsilyl)anthracene and its solvent-separated radical ion pair [((H 3C) 3Si) 2C 14H 8 •−]-[Na +(DME) 3], and in the light of literature examples and the results of MNDO calculations.
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