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N-1- and N-2-anthryl succinimide derivatives: C-N bond rotational behaviors and fluorescence energy transfer.

New rigid bicyclic N-anthrylsuccinimide 1a, 1b, 2a, and 2b were prepared. The C(aryl)-N(imide) bond rotational barriers, intra/intermolecular arene-arene interactions, and photophysical properties were investigated. The rotational behaviors are more significantly controlled by the position of C(aryl)-N(imide) connection than the sidewall framework. The fluorescence energy transfer (Φ(ET)) in 1a and 1b was estimated to be 61% and 53%, respectively. The difference is attributed to the position of C(aryl)-N(imide) connection, which directly influences the relative orientation of donor (naphthalene) and acceptor (anthracene).