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Singlet exciton fission photovoltaic technology requires chromophores with their lowest excited states arranged so that 2E(T1) less then E(S1) and E(S1) less then E(T2). Herein, qualitative theory and quantum chemical calculations are used to develop explicit strategies on how to use Baird's 4n rule on excited-state aromaticity, combined with Hückel's 4n + 2 rule for ground-state aromaticity, to tailor new potential chromophores for singlet fission. We first analyze the E(T1), E(S1), and E(T2) of benzene and cyclobutadiene (CBD) as exc
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